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9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one
The title compound, C(15)H(18)O(3), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The seven-membered ring of the ti...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3275063/ https://www.ncbi.nlm.nih.gov/pubmed/22347008 http://dx.doi.org/10.1107/S1600536812000165 |
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author | Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Mellouki, Fouad Berraho, Moha |
author_facet | Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Mellouki, Fouad Berraho, Moha |
author_sort | Moumou, Mohamed |
collection | PubMed |
description | The title compound, C(15)H(18)O(3), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The seven-membered ring of the title compound shows a chair conformation, while the five-membered rings exibit different conformations, viz a twisted one for the lactone ring and an envelope conformation for the other five-membered ring with the C atom closest to the hydroxy group forming the flap. In the crystal, O—H⋯O hydrogen bonds connect molecules into dimers that are interconnected by C—H⋯O interactions, producing supramolecular chains along the b axis. |
format | Online Article Text |
id | pubmed-3275063 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32750632012-02-15 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Mellouki, Fouad Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(15)H(18)O(3), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.0(2,4)]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The seven-membered ring of the title compound shows a chair conformation, while the five-membered rings exibit different conformations, viz a twisted one for the lactone ring and an envelope conformation for the other five-membered ring with the C atom closest to the hydroxy group forming the flap. In the crystal, O—H⋯O hydrogen bonds connect molecules into dimers that are interconnected by C—H⋯O interactions, producing supramolecular chains along the b axis. International Union of Crystallography 2012-01-14 /pmc/articles/PMC3275063/ /pubmed/22347008 http://dx.doi.org/10.1107/S1600536812000165 Text en © Moumou et al. 2012 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 Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Mellouki, Fouad Berraho, Moha 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one |
title | 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one |
title_full | 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one |
title_fullStr | 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one |
title_full_unstemmed | 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one |
title_short | 9β-Hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3H)-one |
title_sort | 9β-hydroxy-6,9-dimethyl-3-methylene-3a,4,8,9,9a,9b-hexahydroazuleno[4,5-b]furan-2(3h)-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3275063/ https://www.ncbi.nlm.nih.gov/pubmed/22347008 http://dx.doi.org/10.1107/S1600536812000165 |
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