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(E)-13-(2-Bromophenyl)micheliolide
The title compound, C(21)H(23)BrO(3) [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-h...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998478/ https://www.ncbi.nlm.nih.gov/pubmed/24764970 http://dx.doi.org/10.1107/S1600536814002177 |
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author | Penthala, Narsimha Reddy Bommagani, Shobanbabu Janganati, Venumadhav Parkin, Sean Crooks, Peter A. |
author_facet | Penthala, Narsimha Reddy Bommagani, Shobanbabu Janganati, Venumadhav Parkin, Sean Crooks, Peter A. |
author_sort | Penthala, Narsimha Reddy |
collection | PubMed |
description | The title compound, C(21)H(23)BrO(3) [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O—H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°. |
format | Online Article Text |
id | pubmed-3998478 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-39984782014-04-24 (E)-13-(2-Bromophenyl)micheliolide Penthala, Narsimha Reddy Bommagani, Shobanbabu Janganati, Venumadhav Parkin, Sean Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(23)BrO(3) [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O—H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°. International Union of Crystallography 2014-02-05 /pmc/articles/PMC3998478/ /pubmed/24764970 http://dx.doi.org/10.1107/S1600536814002177 Text en © Penthala et al. 2014 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 Penthala, Narsimha Reddy Bommagani, Shobanbabu Janganati, Venumadhav Parkin, Sean Crooks, Peter A. (E)-13-(2-Bromophenyl)micheliolide |
title | (E)-13-(2-Bromophenyl)micheliolide |
title_full | (E)-13-(2-Bromophenyl)micheliolide |
title_fullStr | (E)-13-(2-Bromophenyl)micheliolide |
title_full_unstemmed | (E)-13-(2-Bromophenyl)micheliolide |
title_short | (E)-13-(2-Bromophenyl)micheliolide |
title_sort | (e)-13-(2-bromophenyl)micheliolide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998478/ https://www.ncbi.nlm.nih.gov/pubmed/24764970 http://dx.doi.org/10.1107/S1600536814002177 |
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