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(1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane
The title compound, C(16)H(24)Br(2)O, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The molecule contains fused six- and seven-membered rings, each linked to a...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629578/ https://www.ncbi.nlm.nih.gov/pubmed/23634065 http://dx.doi.org/10.1107/S1600536813006077 |
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author | Oukhrib, Abdelouahd Benharref, Ahmed Saadi, Mohamed Berraho, Moha El Ammari, Lahcen |
author_facet | Oukhrib, Abdelouahd Benharref, Ahmed Saadi, Mohamed Berraho, Moha El Ammari, Lahcen |
author_sort | Oukhrib, Abdelouahd |
collection | PubMed |
description | The title compound, C(16)H(24)Br(2)O, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The molecule contains fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55 (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6 (2) and 80.5 (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each molecule is linked to its symmetry-equivalent partner by C—H⋯O hydrogen bonds, forming zigzag chains parallel to [100]. |
format | Online Article Text |
id | pubmed-3629578 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-36295782013-04-30 (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane Oukhrib, Abdelouahd Benharref, Ahmed Saadi, Mohamed Berraho, Moha El Ammari, Lahcen Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(24)Br(2)O, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The molecule contains fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55 (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6 (2) and 80.5 (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each molecule is linked to its symmetry-equivalent partner by C—H⋯O hydrogen bonds, forming zigzag chains parallel to [100]. International Union of Crystallography 2013-03-09 /pmc/articles/PMC3629578/ /pubmed/23634065 http://dx.doi.org/10.1107/S1600536813006077 Text en © Oukhrib et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Oukhrib, Abdelouahd Benharref, Ahmed Saadi, Mohamed Berraho, Moha El Ammari, Lahcen (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
title | (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
title_full | (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
title_fullStr | (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
title_full_unstemmed | (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
title_short | (1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
title_sort | (1s,3r,8r,9r,10s)-2,2-dibromo-3,7,7,10-tetramethyl-9β,10β-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0(1,3)]dodecane |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629578/ https://www.ncbi.nlm.nih.gov/pubmed/23634065 http://dx.doi.org/10.1107/S1600536813006077 |
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