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Journal articles on the topic 'Bicyclo[2.2.1]heptane'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Werstiuk, N. H., S. Yeroushalmi, and Hong Guan-Lin. "Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicyclo[2.2.1]heptane-2,5-dione and bicyclo[2.2.2]octane-2,5-dione. An AM1 computational study of bicyclic enolates." Canadian Journal of Chemistry 70, no. 3 (March 1, 1992): 974–80. http://dx.doi.org/10.1139/v92-130.

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A group of bicyclic ketones and thiones have been synthesized for homenolization studies. Bicyclo[2.2.1]heptane-2,5-dione (6) undergoes unusually rapid tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dione (1) in good yield. Treatment of 1 with P2S5 in xylene gave 3,3,6,6-tetramethylbicyclo[2.2.1]heptane-2,5-dithione (2) and 3,3,6,6-tetramethyl 15-oxo-bicyclo[2.2.1]heptane-2-thione (3), which was converted into 4 with Raney nickel. Bicyclo[2,2,2]octane-2,5-dione (7), prepared via a Diels–Alder reaction between 2-trimethylsilyloxy-1,3-cyclohexadiene and and α-acetoxyacrylonitrile followed by a one-step desilylation/hydrolysis, also undergoes facile tetramethylation giving 3,3,6,6-tetramethylbicyclo[2.2.2]octane-2,5-dione (5) in good yield. AM1 calculations were carried out on the α-enolates of bicyclo[2.2.1]heptan-2-one, 6, 5-methylidenebicyclo[2.2.1]heptan-2-one, and 4-acetylbicyclo[2.2.1]-heptan-2-one in an attempt to gain information on the source of the enhanced acidity of the C-3 hydrogens of 6 and 7. Keywords: bicyclic ketones, thiones, synthesis.

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2

Hřebabecký, Hubert, Milena Masojídková, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 3-(Hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 871–88. http://dx.doi.org/10.1135/cccc20060871.

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(1R*,2R*,3R*,4R*,5R*,6S*)-3-Amino-5-(benzyloxy)-6-(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (18) was prepared in seven easy steps from benzyl (1R*,2S*,3S*,4S*)-3-(benzyloxy)bicyclo[2.2.1]hept-5-ene-2-carboxylate (10). Reaction of amine18with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded 1-[(1R*,2R*,3R*,4R*,5S*,6R*)-6-(benzyloxy)-3-hydroxy-5- (hydroxymethyl)bicyclo[2.2.1]heptan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (21) and after deprotection by transfer hydrogenation, free thymine analogue22. The thymine derivative21was converted to 2,3'-anhydronucleoside26. Treatment of the benzyl derivative18with sodium in liquid ammonia led to amine19, which was used as key intermediate for the construction of (1R*,2R*,3R*,4R*,5R*,6S*)-3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)-bicyclo[2.2.1]heptane-2,5-diol (28) and (1R*,2R*,3R*,4R*,5R*,6S*)-3-(2-amino-6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]heptane-2,5-diol (33). Ammonolysis of28led to 6-amino-9H-purine derivative29. 6-(Dimethylamino)-9H-purine analogue30and 6-(cyclopropylamino)-9H-purine analogues31and34were prepared by aminolysis of corresponding chloropurine derivatives.

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3

Tanase, Constantin I., Anamaria Hanganu, and Constantin Draghici. "Trifluoroacetylation of Alcohols During NMR Study of Compounds with Bicyclo[2.2.1]heptane, Oxabicyclo[3.3.0]octane and Bicyclo[3.3.0]octane Skeleton." Revista de Chimie 72, no. 2 (May 7, 2021): 156–77. http://dx.doi.org/10.37358/rc.21.2.8428.

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TFA was added to a solution of a bicyclo[2.2.1]heptane azide-alcohol in CDCl3 to correctly characterize the compound, but during 24 h gave the trifluoro acetylated compound in quantitative yield. NMR spectra of the esterified compound helped us also to correctly attribute the NMR signals to the protons, and also confirmed the identification of the carbon atoms. The study was extended to other 14 compounds containing a primary alcohol group alone or with an ethylene ketal, a δ- or -lactone group, a primary and a secondary group, two primary and an alkene group and two primary and a secondary alcohol groups on scaffolds containing bicyclo[2.2.1]heptane, oxabicyclo[3.3.0]octane, bicyclo [2.2.1]heptane constrained with a cyclopropane ring and bicyclo[3.3.0]octane fragments. The esterification of all compounds was also quantitative in 24 to 72 h; this helped us to correct attribute the NMR signals to the protons and carbon atoms of the un-esterified compounds by comparison with those of the trifluoro acetylated compounds. A graphical presentation of 1H- and 13C-NMR spectra of a few un-esterified and esterified compounds are presented in the paper.

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4

Liu, Qi Mei, and Wan Xi Peng. "80°С-Based TD-GC/MS Analysis of Chemical Components from Branches of Cinnamomum camphora." Key Engineering Materials 480-481 (June 2011): 466–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.466.

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The analytical result by 80°С-based TD-GC/MS showed that 65 peaks were obtained from the helium volatiles from the fresh branches of Cinnamomum camphora and 60 chemical compounds were identified. The results showed that the main components were as: 1,3-Benzodioxole, 5-(2-propenyl)- (12.629%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (10.302%), 3-Cyclohexene-1-methanol, .alpha.,.alpha.4-trimethyl- (9.084%), Bicyclo[2.2.1] heptan-2-one, 1,7,7-trimethyl-, (1R)- (7.406%), Nerolidol (6.695%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S-exo)- (6.017%), Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (.+/-.)- (4.885%), Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (4.680%), Naphthalene, 1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.139%), 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)- (3.538%), Copaene (2.749%), Bicyclo[2.2.1] heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)- (2.643%), Acetic acid, 1,7,7-trimethyl-bicyclo [2.2.1]hept-2-yl ester (2.536%), Cyclohexane, bromo- (2.530%), 1,6,10-Dodecatriene, 7,11- dimethyl-3-methylene-, (E)- (1.725%), Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-7-methyl-4- methylene-1-(1-methylethyl)-, (1.alpha.,4a.beta.,8a.alpha.)- (1.265%), Bicyclo[4.4.0]dec-1-ene, 2-isopropyl-5-methyl-9-methylene- (1.174%), (-)-Isosativene (1.149%), 11-Tetradecen-1-ol acetate (1.118%), .alpha.-Cadinol (1.061%), etc. The analytical result suggested that the helium volatiles from the fresh branches of C. camphora could be used as industrial materials of biomedicines, spicery and food industry.

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5

Wermuth, Urs D., Ian D. Jenkins, Raymond C. Bott, Karl A. Byriel, and Graham Smith. "Some Stereochemical Aspects of the Strecker Synthesis and the Bucherer - Bergs Reaction." Australian Journal of Chemistry 57, no. 5 (2004): 461. http://dx.doi.org/10.1071/ch03202.

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Both the Strecker and Bucherer–Bergs reactions convert the norbornane keto ester methyl bicyclo[2.2.1]hept-6-one-2-endo-carboxylate into the lactam 6-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylic acid-γ-lactam-6-exo-carboxylic acid. This lactam is unusually stable and cannot be hydrolyzed to the corresponding amino acid. The stereochemistry in the Strecker reaction, in which the amino group is endo, is contrary to that expected from literature precedent. The stereochemistry in the Bucherer–Bergs reaction, in which the amino group is also endo, has been confirmed by X-ray crystallographic analysis of the intermediate spirohydantoin (±)-bicyclo[2.2.1]heptane-2-endo-carboxylic acid-6-spiro-5′-hydantoin.

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6

Che, Jin-Xin, Zhi-Long Wang, Xiao-Wu Dong, You-Hong Hu, Xin Xie, and Yong-Zhou Hu. "Bicyclo[2.2.1]heptane containing N,N′-diarylsquaramide CXCR2 selective antagonists as anti-cancer metastasis agents." RSC Advances 8, no. 20 (2018): 11061–69. http://dx.doi.org/10.1039/c8ra01806e.

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7

Rehse, Klaus, Peter Sparfeldt, and Wolfgang Kehr. "Neuropsychotrope aktivität dopaminanaloger bicyclo[2.2.1]-heptane." Archiv der Pharmazie 320, no. 10 (October 1987): 1042–50. http://dx.doi.org/10.1002/ardp.198700007.

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8

Liu, Qi Mei, Dang Quan Zhang, Kuan Peng, and Wan Xi Peng. "Deep Analysis on Bioindustry Prospects of 40°С Volatiles of Cinnamomum camphora Branches." Key Engineering Materials 480-481 (June 2011): 266–71. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.266.

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Cinnamomum camphora has been used to heal some specific diseases in the Chinese Folk for a long time. In order to explore the wide utilization in biomedicine and spicery, the chemical components of helium volatiles from the fresh branches of C. camphora were studied by TD-GC/MS. The analytical result by TD-GC/MS showed that 50 peaks were obtained from the helium volatiles from the fresh branches of C. camphora and 46 chemical compounds representing 99.993% of the total areas were identified. The results showed that the main components were as: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)- (9.620%), 3-Cyclohexene-1- methanol, .alpha.,.alpha.4-trimethyl- (9.425%), 1,3-Benzodioxole, 5-(2-propenyl)- (8.223%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-, (1S-exo)- (7.541%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (6.884%), Bicyclo[3.1.1] hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (6.050%), Bicyclo[2.2.1]heptan-2-one, 1,7,7- trimethyl-, (1S)- (4.678%), 1,3-Benzodioxole, 5-(2-propenyl)- (4.500%), Naphthalene, 1,2,3,5,6,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.491%), 3-Cyclohexen-1-ol, 4-methyl-1- (1-methylethyl)-, (R)- (4.254%), Copaene (4.120%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7- (4-methyl-3-pentenyl)-, (-)- (4.097%), Acetic acid, 1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (3.574%), Borneol 3.334%), 3-(4-N,N-Dimethylaminophenyl)propenoic acid, 2- (diethoxyphosphinyl)-, ethyl ester (2.809%), Eucalyptol (2.096%), 1,6,10-Dodecatriene, 7,11- dimethyl-3-methylene-, (Z)- (1.885%), (-)-Isosativene (1.664%), 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl- (1.407%), Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexenyl)-, (S)- (1.218%), 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene-, [1S-(1.alpha.,3a.beta., 4.alpha.,8a.beta.)]- (1.174%), .alpha.-Caryophyllene (1.156%), etc. The analytical result suggested that the helium volatiles from the fresh branches of C. camphora can be applicable to biomedicine and spicery industrial materials.

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9

Tanase, Constantin I., Constantin Draghici, Catalina Negut, and Lucia Pintilie. "New Constrained Amines in a Bicyclo[2.2.1]Heptane Skeleton." Revista de Chimie 69, no. 9 (October 15, 2018): 2448–53. http://dx.doi.org/10.37358/rc.18.9.6551.

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In this paper we present an efficient procedure for obtaining ether-protected bicyclo[2.2.1]heptane amines in six steps, from an optically active keto-alcohol norbornane compound, for building the heterocyclic bases of pyrimidine and purine constrained nucleosides. Trityl as protecting group makes it possible to isolate 5-endo-compounds in pure form by selective crystallization, and to isolate the intermediates in the next 3 steps of the reaction by crystallization. With TBDMS, all compounds were obtained as oil. The direct selective reduction of the keto-alcohol norbornane compound gave the pure 5-endo-diol 4d in high yield, which was then selectively protected at the primary hydroxyl with a trityl group; the next steps are similar for obtaining the trityl-protected bicyclo[2.2.1]heptane amine. The azide intermediates are valuable intermediates for click chemistry.

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10

Šála, Michal, Hubert Hřebabecký, Martin Dračínský, Milena Masojídková, Armando M. De Palma, Johan Neyts, and Antonín Holý. "Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene." Collection of Czechoslovak Chemical Communications 75, no. 1 (November 28, 2009): 1–20. http://dx.doi.org/10.1135/cccc2009116.

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Novel class of the carbocyclic nucleosides based on bicyclo[2.2.1]heptene/heptane was prepared by two approaches. Thymine analogues were synthesized starting from methyl (1R*,4S*)-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate1by Michael addition of the thymine salt to the double bond as the key step. The yield and ratio of the isomers of this reaction depended on the used base (DBU, K2CO3). Purine nucleoside analogues were synthesized by the linear synthesis, the purine nucleobase was build-up on the amino group. The amino groups (exo/endoconfiguration) were introduced to the scaffold by the Curtius rearrangement. Norbornene analogues were converted to saturated andcis-hydroxylated nucleoside derivatives. [(1R*,2S*,3S*,4S*)-3-(6-Chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-yl]methanol (13a) and [(1R*,2R*,3R*,4S*)-3-(6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-yl]methanol (13b) showed moderate activity againstCoxsackievirus CVB3.

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11

Fu, Jian-Guo, Yi-Fan Shan, Wang-Bin Sun, Guo-Qiang Lin, and Bing-Feng Sun. "An asymmetric approach to bicyclo[2.2.1]heptane-1-carboxylates via a formal [4 + 2] cycloaddition reaction enabled by organocatalysis." Organic & Biomolecular Chemistry 14, no. 23 (2016): 5229–32. http://dx.doi.org/10.1039/c6ob00814c.

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An organocatalytic formal [4 + 2] cycloaddition reaction has been developed that permits rapid access to bicyclo[2.2.1]heptane-1-carboxylates with excellent enantioselectivities under mild and operationally simple conditions.

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12

Li, Qing, Dang Quan Zhang, Qi Mei Liu, and Kuan Peng. "Determination of Bioactive Components of 60°С Volatiles from Cinnamomum camphora Branches by TD-GC/MS." Advanced Materials Research 230-232 (May 2011): 852–56. http://dx.doi.org/10.4028/www.scientific.net/amr.230-232.852.

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The chemical components of helium volatiles from the fresh branches of Cinnamomum camphora were studied by TD-GC/MS. The analytical result by 60°С-based TD-GC/MS showed that 55 peaks were obtained from the helium volatiles from the fresh branches of Cinnamomum camphora and 53 chemical compounds were identified. The results showed that the main components were as: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)- (15.4328%), 1,3-Benzodioxole, 5-(2-propenyl)- (14.881%), Tricyclo[2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (12.694%), p-menth-1-en-8-ol (9.832%), Bicyclo[2.2.1]heptane, 2-methyl-3-methylene-2-(4-methyl-3- pentenyl)-, (1S-exo)- (6.143%), 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl- (5.365%), Bicyclo[3.1.1] hept-2-ene, 2,6-dimethyl-6-(4-methyl-3-pentenyl)- (4.527%), Naphthalene, 1,2,3,5,6,8a- hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S-cis)- (4.129%), 3-Cyclohexen-1-ol, 4-methyl-1- (1-methylethyl)- (2.965%), Borneol (2.627%), Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1S-endo)- (2.586%), Copaene (2.534%), 1,6,10-Dodecatriene, 7,11-dimethyl-3-methylene-, (Z)- (1.612%), (-)-Isosativene (1.121%), etc. The analytical result suggested that the helium volatiles from the fresh branches of Cinnamomum camphora could be used as industrial materials of biomedicines and spicery.

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13

Adcock, William, and Dieter Lunsmann. "Effects of Bridgehead Substituents on the Stability of the 1-Norbornyl Radical." Collection of Czechoslovak Chemical Communications 64, no. 10 (1999): 1572–82. http://dx.doi.org/10.1135/cccc19991572.

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The electrochemical reductive cleavage of a series of 4-X-substituted bicyclo[2.2.1]heptan- 1-yl bromides and iodides (X = H, F, Cl, Br, I, SnMe3) was investigated by means of cyclic voltammetry. By application of the dissociative electron-transfer theory, the variations in the peak reduction potentials translate to values for the weakening of the C-Br and C-I bond dissociation energies (∆D) upon replacement of H by all the substituents (X). The ∆D values suggest significant through-space stabilizing interactions (homohyperconjugation) in the 4-X-substituted bicyclo[2.2.1]heptane radical species.

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14

Moilanen, Maija, Kalle Manninen, Kurt B. G. Torssell, Jyrki M. Loponen, Erkki K. Euranto, and Tore Pettersson. "Aminomethylation of Bicyclo[2.2.1]heptane-2,5-dione." Acta Chemica Scandinavica 44 (1990): 857–59. http://dx.doi.org/10.3891/acta.chem.scand.44-0857.

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15

Fukunaga, Kimitoshi, and Christoph Rüchardt. "A Convenient Synthesis of 7-Nitrobicyclo[2.2.1]heptane from Bicyclo[2.2.1]hept-2-enevia7-Aminobicyclo[2.2.1]heptane." Synthesis 1987, no. 12 (1987): 1097–98. http://dx.doi.org/10.1055/s-1987-28181.

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16

Jin, Song, Norbert G. Swoboda-Colberg, and Patricia J. S. Colberg. "Microbial degradation of quadricyclane-derived tricyclo[2.2.1.02,6]heptan-3-ol in soil." Canadian Journal of Microbiology 43, no. 3 (March 1, 1997): 300–303. http://dx.doi.org/10.1139/m97-042.

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Quadricyclane (tetracyclo[3.2.02,7.04,6]heptane) is a strained, saturated cyclic hydrocarbon and a potential environmental contaminant because of uses in solar energy and optical memory storage devices and as a recently proposed additive to jet fuel. Quadricyclane is very unstable in both soil and water, and in the environment it exists as abiotic transformation products, tricyclo[2.2.1.02,6]heptan-3-ol and bicyclo[2.2.1]hept-5-en-2-ol. In soils, tricyclo[2.2.1.02,6]heptan-3-ol is microbially transformed to a C7H8O intermediate which we postulate to be tricyclo[2.2.1.02,6]heptan-3-one. This compound is subsequently biodegraded over several months. Elevated respiration rates in soils amended with tricyclo[2.2.1.02,6]heptan-3-ol provide evidence that it is mineralized to CO2, while bicyclo[2.2.1]hept-5-en-2-ol concentrations in soil microcosms remained unchanged over a period of 8 months.Key words: quadricyclane, biotransformation, biodégradation, tricyclo[2.2.1.02,6]heptan-3-ol, bicyclo[2.2.1]hept-5-en-2-ol.

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17

Tănase, Drăghici, Hanganu, Pintilie, Maganu, Volobueva, Sinegubova, et al. "New HSV-1 Anti-Viral 1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Fragment as a Glycoside Moiety." Molecules 24, no. 13 (July 3, 2019): 2446. http://dx.doi.org/10.3390/molecules24132446.

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New 1′-homocarbanucleoside analogs with an optically active substituted bicyclo[2.2.1]heptane skeleton as sugar moiety were synthesized. The pyrimidine analogs with uracil, 5-fluorouracil, thymine and cytosine and key intermediate with 6-chloropurine (5) as nucleobases were synthesized by a selective Mitsunobu reaction on the primary hydroxymethyl group in the presence of 5-endo-hydroxyl group. Adenine and 6-substituted adenine homonucleosides were obtained by the substitution of the 6-chlorine atom of the key intermediate 5 with ammonia and selected amines, and 6-methoxy- and 6-ethoxy substituted purine homonucleosides by reaction with the corresponding alkoxides. No derivatives appeared active against entero, yellow fever, chikungunya, and adeno type 1viruses. Two compounds (6j and 6d) had lower IC50 (15 ± 2 and 21 ± 4 µM) and compound 6f had an identical value of IC50 (28 ± 4 µM) to that of acyclovir, suggesting that the bicyclo[2.2.1]heptane skeleton could be further studied to find a candidate for sugar moiety of the nucleosides.

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18

Walton, John C. "Free radical reactions of bicyclo[2.1.1]hexane and bicyclo[2.2.1]heptane." Journal of the Chemical Society, Perkin Transactions 2, no. 11 (1988): 1989. http://dx.doi.org/10.1039/p29880001989.

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19

Della, EW, and J. Tsanaktsidis. "Synthesis of Bridgehead-Bridgehead Substituted Bicycloalkanes." Australian Journal of Chemistry 38, no. 11 (1985): 1705. http://dx.doi.org/10.1071/ch9851705.

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A convenient synthetic route to several bicycloalkanes bearing substitution at both bridgehead positions is described. The two-step procedure, which involves alkylation of the monoenolates of readily available cyclohexane diesters with 1,2-dihaloethane followed by a base-induced cyclization of the derived haloethylated product, was successfully applied to the synthesis of dimethyl bicyclo[2.2.2]octane- 1,4-dicarboxylate, dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate and dimethyl bicyclo[3.2.1]octane-1,5-dicarboxylate. Additionally, it was found that the two latter diesters could be obtained in quite acceptable yields in a one-pot procedure through their corresponding cyclohexyl bisenolate precursors.

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20

Ogunmola, Oluranti O. "CHEMICAL COMPOSITIONS AND ANTIMICROBIAL ACTIVITY OF THE LEAF ESSENTIAL OIL OF GOSSYPIUM HIRSUTUM." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 23, no. 23 (December 20, 2015): 91–100. http://dx.doi.org/10.48141/sbjchem.v23.n23.2015.91_revista2015.pdf.

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The study was conducted to analyze the chemical constituent and to evaluate the antimicrobial properties of the leaf essential oil of Gossypium hirsutum. The oil was obtained by hydrodistillation and was analyzed by gas chromatography and gas chromatography-mass spectrometry (GC/GC-MS). This revealed the presence of fifty components accounting for - % of the total oil fraction. The leaf oil was dominated by patchoulane (14.70%), Ally 1-2, 6,6–trimethyl bicyclo (3.1.1) heptane (5.95%). 1,7, 7 – trimethyl bicyclo (2.2.1) heptanes (5.95%)and 9- (1 – methylethylidene) bicyclo (6.1.0) nonane (5.95%). The oil displayed high antimicrobial potentials to some tested microorganisms.

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21

Tauchman, Jiří, M. Fernanda N. N. Carvalho, and Petr Štěpnička. "Selective hydration of ferrocenylethyne mediated by a palladium complex with a camphorhydrazone ligand." Collection of Czechoslovak Chemical Communications 76, no. 11 (2011): 1277–83. http://dx.doi.org/10.1135/cccc2011130.

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Complex [PdCl2L2], where L is a camphor hydrazone ligand, (1R,4S)-1,7,7-trimethyl-3-(2,2-dimethylhydrazone)-bicyclo[2.2.1]heptane-2,3-dione, efficiently promotes Markovnikov hydration of ethynylferrocene to acetylferrocene in aqueous methanol at room temperature. 1-Ferrocenylprop-1-yne and simple organic alkynes such as 1-octyne or ethynylbenzenes are not affected or polymerize under the reaction conditions.

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22

Burnell, D. Jean, and Zdenek Valenta. "π-Facial stereoselectivity in the Diels–Alder reactions of a rigid carbocyclic diene: spiro(bicyclo[2.2.1]heptane-2,1′-[2,4]cyclopentadiene)." Canadian Journal of Chemistry 69, no. 1 (January 1, 1991): 179–84. http://dx.doi.org/10.1139/v91-028.

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The plane-nonsymmetrical diene spiro(bicyclo[2.2.1]heptane-2,1′-[2,4]cyclopentadiene) (2) was synthesized, and the π-facial stereoselectivity of its Diels–Alder cycloadditions with three cyclic dienophiles was examined. Adduct ratios were very similar, and the selectivity is surmised to be mainly the result of steric interactions at the transition state. Key words: facial stereoselectivity, Diels–Alder, cycloaddition.

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23

Bjørnland, Terje, Gunner Borch, and Synnøve Liaaen-Jensen. "Additional oxa-bicyclo[2.2.1]heptane carotenoids from Eutreptiella gymnastica." Phytochemistry 25, no. 1 (December 1985): 201–5. http://dx.doi.org/10.1016/s0031-9422(00)94529-1.

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24

Matsumoto, Toshihiko. "Semiaromatic Polyimides based on Bis(Aminomethyl)Bicyclo[2.2.1]Heptane." High Performance Polymers 11, no. 4 (December 1999): 367–77. http://dx.doi.org/10.1088/0954-0083/11/4/302.

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25

Yamazaki, Yoshimitsu, and Hidekatsu Maeda. "Enantioselective microbial hydroxylation of bicyclo(2.2.1)heptane carbon skeleton." Tetrahedron Letters 26, no. 39 (January 1985): 4775–76. http://dx.doi.org/10.1016/s0040-4039(00)94948-7.

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26

Witt, Matthias, Dirk Kreft, and Hans-Friedrich Grützmacher. "Effects of Internal Hydrogen Bonds between Amide Groups: Protonation of Alicyclic Diamides." European Journal of Mass Spectrometry 9, no. 2 (April 2003): 81–95. http://dx.doi.org/10.1255/ejms.535.

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The proton affinity ( PA) of cyclopentane carboxamide 1, cyclohexane carboxamide 2 and their secondary and tertiary amide derivatives S1, S2, T1 and T2, was determined by the thermokinetic method and the kinetic method [ PA(1) = 888 ± 5 kJ mol−1; PA(2) = 892 ± 5 kJ mol−1; PA(S1) = 920 ± 6 kJ mol−1; PA(S2) = 920 ± 6 kJ mol−1; PA(T1) = 938 ± 6 kJ mol−1; PA(T2) = 938 ± 6 kJ mol−1]. Special entropy effects are not observed. Additionally, the effects of protonation have been studied using an advanced kinetic method for all isomers 3–7 of cyclopentane dicarboxamides and cyclohexane dicarboxamides (with the exception of cis-cyclopentane-1,2-dicarboxamide) and their bis-tertiary derivatives T3–T7 by estimating the PA and the apparent entropy of protonation Δ(Δ Sapp). Finally, the study was extended to bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxamide 8 and its bis-tertiary derivative T8, to all stereoisomers of bicyclo[2.2.1]heptane-2,3-dicarboxamide 9, their secondary and tertiary amide derivatives S9 and T9, and to endo–endo–bicyclo[2.2.1]heptane-2,5-dicarboxamide 10 and the corresponding secondary and tertiary derivatives S10 and T10. Compared with 1 and 2, all alicyclic diamides exhibit a significant increase of the PA (ΔPA) and special entropy effects on protonation. For alicyclic diamides, which can not accommodate a conformation appropriate for building a proton bridge, the values of Δ PA and Δ(Δ Sapp) are small to moderate. This is explained by ion / dipole interactions between the protonated and neutral amide group which stabilize the protonated species but hinder the free rotation of the amide groups. If any of the conformations of the alicyclic diamide allows formation of a proton bridge, Δ PA and Δ(Δ Sapp) increase considerably. A spectacular case is cis-cyclohexane-1,4-dicarboxamide 7c which is the most basic monocyclic diamide, although generation of the proton bridge requires the unfavorable boat conformation with both amide substituents at a flagpole position. A pre-orientation of the two amide groups in such a 1,4-position in 10 results in a particularly large PA of < 1000 kJ mol−1. The observation of comparable values for Δ(Δ Sapp) for linear and monocyclic diamides indicates that a major part of the entropy effects originates from freezing the free rotation of the amide groups by formation of the proton bridge. This is corroborated by observing corresponding effects during the protonation of dicarboxamides containing the rigid bicyclo[2.2.1]heptane carbon skeleton, where the only internal movements of the molecules corresponds to rotation of the amide substituents.

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27

Dejmek, Milan, Hubert Hřebabecký, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Carbocyclic Nucleoside Analogues Derived from 2-(Hydroxymethyl)bicyclo[2.2.1]heptane." Collection of Czechoslovak Chemical Communications 72, no. 11 (2007): 1523–44. http://dx.doi.org/10.1135/cccc20071523.

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The key intermediates, [(1R*,2R*,4R*,6R*)-6- (12a) and [(1R*,2R*,4R*,5S*)-5-(hydroxymethyl)- bicyclo[2.2.1]heptan-2-yl]methyl benzoates (12b), were prepared from (1R*,2S*,4R*)- bicyclo[2.2.1]hept-5-en-2-ylmethyl benzoate by hydroboration, oxidation with pyridinium dichromate and subsequent reduction of the thus obtained ketones. The Mitsunobu reaction of12aand12bwith 6-chloropurine afforded 6-chloropurine derivatives, which were converted into others purine analogues. Thymine analogues were prepared from [(1R*,2R*,4S*,6S*)-6- (25a) and [(1R*,2S*,4R*,5S*)-5-aminobicyclo[2.2.1]heptan-2-yl]methanols (25b), which were prepared from alcohols12aand12bin several easy steps.

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28

Ustabaş, Reşat, Ufuk Çoruh, Metin Yavuz, Emine Salamci, and Ezequiel M. Vázquez-López. "(2RS,3SR,5RS,6SR)-Bicyclo[2.2.1]heptane-2,3,5,6-tetryl tetraacetate." Acta Crystallographica Section E Structure Reports Online 62, no. 3 (February 24, 2006): o1149—o1150. http://dx.doi.org/10.1107/s1600536806006143.

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29

Yamada, Masao, Masatoshi Kusama, Toshihiko Matsumoto, and Toshikazu Kurosaki. "Synthesis of bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic 2,3:5,6-dianhydrides." Journal of Organic Chemistry 57, no. 22 (October 1992): 6075–77. http://dx.doi.org/10.1021/jo00048a055.

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30

Malinowska, Anna, Izabela Czeluśniak, Marcin Górski, and Teresa Szymańska-Buzar. "A novel catalytic route to 2-bicyclo[2.2.1]hept-2-ylidenebicyclo[2.2.1]-heptane involving CH bond activation of bicyclo[2.2.1]hept-2-ene." Journal of Molecular Catalysis A: Chemical 226, no. 2 (February 2005): 259–62. http://dx.doi.org/10.1016/j.molcata.2004.10.040.

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31

Manukhov, I. V., L. S. Yaguzhinsky, M. V. Bermeshev, M. A. Zisman, V. G. Pevgov, V. O. Samoilov, S. V. Shorunov, and A. L. Maksimov. "Toxic Effect of 2-ethyl (bicyclo[2.2.1] heptane) on Bacterial Cells." Biotekhnologiya 35, no. 6 (2019): 67–72. http://dx.doi.org/10.21519/0234-2758-2019-35-6-67-72.

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Toxic effect of 2-ethylnorbornane (2-ethyl(bicyclo[2.2.1]heptane) (EBH)) on bacteria has been studied using the E. coli pRecA-lux and E. coli pKatG- lux cells as lux-biosensors. It was shown that the addition of EBH to the incubation medium leads to death and growth retardation, high level oxidative stress and DNA damage in E. coli cells. It is assumed that the oxidation of EBH with atmospheric oxygen causes the formation of reactive oxygen species in the medium, which makes a major contribution to the toxicity of this substance. biosensor, luciferase, bioluminescence, inducible promoter, PrecA, PkatG The authors are grateful to Stanislav Filippovich Chalkin for the development of interdisciplinary ties in the scientific community. The work was financially supported by the Ministry of Higher Education and Science of Russia (Project Unique Identifier RFMEFI60417X0181, Agreement No. 14.604.21.0181 of 26.09.2017).

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32

Huang, Kun, Yi-Zhi Li, Sen-Zhi Zhao, Xin-Liang Li, and Zhi-Zhen Huang. "1,3′,7,7-Tetramethylspiro[bicyclo[2.2.1]heptane-2,2′-thiolane] 1′,1′-dioxide." Acta Crystallographica Section E Structure Reports Online 62, no. 8 (July 12, 2006): o3237—o3238. http://dx.doi.org/10.1107/s1600536806025372.

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33

Kessenikh, A., E. Gnuchikh, S. Bazhenov, M. Bermeshev, V. Pevgov, V. Samoilov, S. Shorunov, A. Maksimov, L. Yaguzhinsky, and I. Manukhov. "Genotoxic effect of 2,2’-bis(bicyclo[2.2.1] heptane) on bacterial cells." PLOS ONE 15, no. 8 (August 21, 2020): e0228525. http://dx.doi.org/10.1371/journal.pone.0228525.

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34

Dallinga, G., and L. H. Toneman. "Electron diffraction by gases: The molecular structure of bicyclo[2.2.1]heptane." Recueil des Travaux Chimiques des Pays-Bas 87, no. 7 (September 2, 2010): 795–804. http://dx.doi.org/10.1002/recl.19680870707.

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35

Hřebabecký, Hubert, Milena Masojídková, and Antonín Holý. "Synthesis of Novel Conformationally Locked Carbocyclic Nucleosides Derived from 5,5- and 6,6-Bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol." Collection of Czechoslovak Chemical Communications 70, no. 4 (2005): 519–38. http://dx.doi.org/10.1135/cccc20050519.

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(1R*,2R*,3R*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (13) was prepared from (bicyclo[2.2.1]hept-5-ene-2,2-diyl)dimethyl dibenzoate (7) viacis-diol8, cyclic sulfate10, and azide12. (1R*,2R*,3S*,4S*)-3-Amino-6,6-bis(hydroxymethyl)bicyclo[2.2.1]-heptan-2-ol (18) and (1R*,2S*,3S*,4S*)-3-amino-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (19) were obtained by addition of chromyl azide to double bond of7, chromatographic separation, debenzoylation and hydrogenation of resulting azides14and16. The amines13,18, and19were used to build (1R*,2R*,3R*,4S*)- (21a), (1R*,2R*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-6,6-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21b), and (1R*,2S*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5,5-bis(hydroxymethyl)bicyclo[2.2.1]heptan-2-ol (21c), respectively. Ammonolysis of these compounds led to 6-amino-9H-purine derivatives22a-22c. 6-(Dimethylamino)-9H-purine analogues23a-23cand 6-(cyclopropylamino)-9H-purine analogues24a-24cwere prepared by aminolysis of21a-21c. Reaction of amines13,18, and19with ethylN-((2E)-3-ethoxymethacryloyl)carbamate afforded thymine derivatives28a-28c.

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36

Britvin, Sergey N., and Andrey M. Rumyantsev. "Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide." Acta Crystallographica Section E Crystallographic Communications 73, no. 12 (November 17, 2017): 1861–65. http://dx.doi.org/10.1107/s2056989017015870.

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The cage of 2,5-diazabicyclo[2.2.1]heptane is frequently employed in synthetic chemistry as a rigid bicyclic counterpart of the piperazine ring. The 2,5-diazabicyclo[2.2.1]heptane scaffold is incorporated into a variety of compounds having pharmacological and catalytic applications. The unsubstituted parent ring of the system, 2,5-diazabicyclo[2.2.1]heptane itself, has not been structurally characterized. We herein report on the molecular structure of the parent ring in (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide, C5H12N22+·2Br−. The asymmetric unit contains two crystallographically independent cages of 2,5-diazabicyclo[2.2.1]heptane. Each cage is protonated at the two nitrogen sites. The overall charge balance is maintained by four crystallographically independent bromide ions. In the crystal, the components of the structure are linkedviaa complex three-dimensional network of N—H...Br hydrogen bonds.

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37

Tănase, Constantin I., Constantin Drăghici, Anamaria Hanganu, Lucia Pintilie, Maria Maganu, Vladimir V. Zarubaev, Alexandrina Volobueva, and Ekaterina Sinegubova. "1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Scaffold." Chemistry Proceedings 3, no. 1 (November 14, 2020): 16. http://dx.doi.org/10.3390/ecsoc-24-08367.

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An optically active bicyclo[2.2.0]heptane fragment was introduced in the molecule of new 1′-homonucleosides on a 2- 6-chloro-amino-purine scaffold to obtain 6-substituted carbocyclicnucleozide analogs as antiviral compounds. The synthesis was realized by a Mitsunobu reaction of the base with the corresponding bicyclo[2.2.0]heptane intermediate, and then the nucleoside analogs were obtained by substitution of the 6-chlorime with selected pharmaceutically accepted amines. A molecular docking study of the compounds on influenza, HSV and low active coronavirus was realized. Experimental screening of the compounds on the same viruses is being developed and soon will be finished.

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38

Hřebabecký, Hubert, Martin Dračínský, and Antonín Holý. "Synthesis of Novel Carbocyclic Nucleoside Analogues Containing Bicyclo[2.2.1]hept-2-ene-2-methanol." Collection of Czechoslovak Chemical Communications 73, no. 1 (2008): 44–58. http://dx.doi.org/10.1135/cccc20080044.

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Starting ethyl (1R*,2R*,3R*,4S*)-3-bromobicyclo[2.2.1]hept-5-ene-2-carboxylate (9) was reduced with LiAlH4and benzoylated giving [(1R*,2R*,3R*,4S*)-3-bromobicyclo[2.2.1]hept-5-en-2-yl]methyl benzoate (11). Treatment of11with NaN3and CrO3in acetic acid afforded [(1R*,2S*,3R*,4R*,5S*,6R*)-6-azido-3-bromo-5-hydroxybicyclo[2.2.1]hept-2-yl]methyl benzoate (12a) and [(1R*,2S*,3S*,4R*,5S*,6R*)-5-azido-3-bromo-6-hydroxybicyclo[2.2.1]heptan-2-yl]-methyl benzoate (12b). These key intermediates were separated and converted in five reaction steps to (1R*,2R*,3S*,4S*)-3-[(5-amino-6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)- bicyclo[2.2.1]hept-5-en-2-ol (17a) and (1R*,2R*,3S*,4S*)-3-[(5-amino-6-chloropyrimidin-4-yl)- amino]-6-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (17b). Ring closure with triethyl orthoformate led to (1R*,2R*,3S*,4S*)-5-(chloromethyl)-3-(6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-5-en-2-ol (18a) and (1R*,2R*,3S*,4S*)-6-(chloromethyl)-3-(6-chloro-9H-purin-9-yl)- bicyclo[2.2.1]hept-5-en-2-ol (18b) using hydrochloric acid as a catalyst or (1R*,2R*,3S*,4S*)-3-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (19a) and (1R*,2R*,3S*,4S*)- 3-(6-chloro-9H-purin-9-yl)-6-(hydroxymethyl)bicyclo[2.2.1]hept-5-en-2-ol (19b) using trifluoro- acetic acid as a catalyst. From19aand19b, 6-amino- and 6-(cyclopropylamino)purine derivatives20and21were prepared.

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39

Thirunarayanan, Ganesamoorthy. "Bio-Potent (5-Chloro-2-Thienyl)-3-(Substituted Phenyl) Bicyclo[2.2.1]Heptane-2-yl Methanone Derivatives." International Letters of Chemistry, Physics and Astronomy 42 (December 2014): 1–12. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.42.1.

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A series of (5-chloro-2-thienyl)(3-(substituted phenyl) bicyclo [2.2.1] hept-5-en-2-yl) methanones have been synthesized by fly-ash catalyzed [4+2] cycloaddition Diels-Alder reaction of cyclopentadiene and 5-chloro-2-thienyl chalcones under cooling conditions. The yields of the methanones are more than 60%. The synthesized (5-chloro-2-thienyl)(3-(substituted phenyl) bicyclo [2.2.1] hept-5-en-2-yl) methanones are characterized by their physical constants and spectral data. The antimicrobial, antioxidant and insect antifeedant activities of synthesized methanones have been studied using their respective bacterial, fungal strains, DPPH radical scavenging activity and Dethler’s leaf-discs bioassay method.

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40

Saha Roy (nee Saha), Supti, and Subrata Ghosh. "Bicyclo [2.2.1]heptane as cyclopentane precursor. synthesis of benzhydropentalenes enroute to terpenoids." Tetrahedron 43, no. 24 (1987): 5995–6000. http://dx.doi.org/10.1016/s0040-4020(01)87805-4.

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41

Yuasa, Yoshifumi, Haruki Tsuruta, and Yoko Yuasa. "The Synthesis and Stereochemistry of Methyl Substituted Bicyclo[2.2.1] heptane-2-carboxaldehydes." Journal of Essential Oil Research 12, no. 6 (November 2000): 679–84. http://dx.doi.org/10.1080/10412905.2000.9712189.

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42

Ihara, Masataka, Shuichi Suzuki, Yuji Tokunaga, and Keiichiro Fukumoto. "Assembly of bicyclo[2.2.1]heptane derivatives by two types of domino reaction." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (1995): 2811. http://dx.doi.org/10.1039/p19950002811.

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43

YAMADA, M., M. KUSAMA, T. MATSUMOTO, and T. KUROSAKI. "ChemInform Abstract: Synthesis of Bicyclo(2.2.1)heptane-2,3,5,6-tetracarboxylic 2,3:5,6- Dianhydrides." ChemInform 24, no. 9 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199309112.

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44

Matsumoto, Toshihiko, Shuichi Kawabata, and Risa Takahashi. "Alicyclic Polyimides based on bicyclo[2.2.1]heptane- 2,3,5,6-tetracarboxylic 2,3-5,6-dianhydrides." High Performance Polymers 18, no. 5 (October 2006): 719–26. http://dx.doi.org/10.1177/0954008306068245.

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45

Levsen, Steven M., Andrew C. Peterson, and Sheldon E. Cremer. "STEREOSELECTIVE PREPARATION OF THE ENDO-2-PHOSPHORUS SUBSTITUTed BICYCLO[2.2.1]HEPTANE SYSTEM." Phosphorus, Sulfur, and Silicon and the Related Elements 123, no. 1 (April 1, 1997): 35–44. http://dx.doi.org/10.1080/10426509708044196.

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46

de Boer, Th J., J. C. van Velzen, and C. Kruk. "Synthesis and stereochemistry of spiro-dihydropyran derivatives derived from bicyclo[2.2.1]heptane." Recueil des Travaux Chimiques des Pays-Bas 88, no. 1 (September 2, 2010): 62–70. http://dx.doi.org/10.1002/recl.19690880110.

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47

Kessenikh, A., E. Gnuchikh, S. Bazhenov, M. Bermeshev, V. Pevgov, V. Samoilov, S. Shorunov, A. Maksimov, L. Yaguzhinsky, and I. Manukhov. "Correction: Genotoxic effect of 2,2’-bis(bicyclo[2.2.1] heptane) on bacterial cells." PLOS ONE 16, no. 3 (March 3, 2021): e0248251. http://dx.doi.org/10.1371/journal.pone.0248251.

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48

Hu, Xiao Yi, Dang Quan Zhang, and Lin Lin Guo. "Py-GC/MS Analysis of Bioactive Components of 550°C Pyrolyzate from Acetone Extractives of Cinnamomum camphora Root Wood." Key Engineering Materials 480-481 (June 2011): 478–83. http://dx.doi.org/10.4028/www.scientific.net/kem.480-481.478.

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The researches are very less about the acetone extractives of rood wood from Cinnamomum camphora, a famous non-wood tree in China. Therefore, 550°C-based Py-GC/MS was used to analyze the high-grade resource recovering approaches of C. camphora root wood. The analytical result showed that the main components of the acetone extractives of C. camphora root wood by 550°C-based pyrolysis- GC/MS are as: Decanoic acid, 1,2,3-propanetriyl ester (16.720%), 4-Nitrophenyl laurate (9.104%), 1,3-Benzodioxole, 5-(2-propenyl)- (6.3744%), Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1R)- (5.646%), 2-Hydroxy-5-methylbenzohydrazide (3.516%), p-menth-1-en-8-ol (3.279%), Benzene, 1,2-dimethoxy-4-(2-propenyl)- (2.686%), Dodecanoic acid, 1,2,3-propanetriyl ester (2.478%), 2,3-Butanediol, [S-(R*,R*)]- (2.177%), Phenol, 2,6-dimethoxy- (2.147%), 2-Oxabicyclo[2.2.2]octan-6-ol, 1,3,3-trimethyl- (1.642%), Tricyclo [2.2.1.0(2,6)]heptane, 1,7-dimethyl-7-(4-methyl-3-pentenyl)-, (-)- (1.349%), Bicyclo[2.2.1] heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)- (1.292%), Acetic acid, 2-acetoxymethyl-1,2,3- trimethylbutyl ester (1.174%), Phenol, 2,6-dimethoxy-4-(2-propenyl)- (1.125%), etc. The result of functional analysis suggested that C. camphora root wood can be used as top value-added materials of biomedicine, and also as the materials of bioenergy, perfume, cosmetic, food, dye and industrial solvent.

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49

Tsuri, Tatsuo, Tsunetoshi Honma, Yoshiharu Hiramatsu, Toshihiko Okada, Hiroshi Hashizume, Susumu Mitsumori, Masanao Inagaki, et al. "Bicyclo[2.2.1]heptane and 6,6-Dimethylbicyclo[3.1.1]heptane Derivatives: Orally Active, Potent, and Selective Prostaglandin D2Receptor Antagonists." Journal of Medicinal Chemistry 40, no. 22 (October 1997): 3504–7. http://dx.doi.org/10.1021/jm970343g.

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50

Kasyan, Lilija, Andrey Kasyan, Igor Tarabara, Sergiy Okovytyy, Elena Golodayeva, Andrey Tokar, and Yevgeniy Podolyan. "Azabrendanes V. Synthesis and reactions of stereoisomeric exo- and endo-5-aminomethylbicyclo[2.2.1]hept-2-ene-based ureas." Open Chemistry 6, no. 2 (June 1, 2008): 161–74. http://dx.doi.org/10.2478/s11532-008-0012-9.

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AbstractA number of stereoisomeric ureas (N-[aryl(benzyl, or cycloalkyl)carbamoyl]-exo(endo)-5-aminomethylbicyclo[2.2.1]hept-2-enes) have been synthesized from bicyclo[2.2.1]hept-2-en-exo(endo)-5-carbonitrile by reduction with lithium aluminum hydride and subsequent reaction of the resulting amines with aryl (benzyl, or cycloalkyl) isocyanates. Regioselective alkylation of stereoisomeric ureas has been performed with benzyl chloride under liquid/solid phase-transfer catalysis. The outcome of the reactions of ureas with peroxy acids is dependent upon the orientation of substituents in the bicyclic fragment. Exo-isomeric ureas are transformed into corresponding epoxy-derivatives, while reactions of the endo-isomers are accompanied by intramolecular cyclization, resulting in the formation of azatricyclononane derivatives. Quantum-chemical calculations have established a decisive role for additional hydrogen bonding in the stabilization of transition states in these heterocyclization reactions of ureas. The structures and stereochemical homogeneity of the products have been confirmed by the analysis of 1H and 13C NMR spectra and correlation spectroscopy. The mechanism of the intramolecular heterocyclization reaction of ureas and carboxamide of endo-5-aminomethyl-exo-2,3-epoxybicyclo[2.2.1]heptane series has been studied at the BHandHLYP/6-31G(d) level of theory.

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