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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...

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Autores principales: Penthala, Narsimha Reddy, Bommagani, Shobanbabu, Janganati, Venumadhav, Parkin, Sean, Crooks, Peter A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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)°.
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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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AT parkinsean e132bromophenylmicheliolide
AT crookspetera e132bromophenylmicheliolide