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10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one
The title compound, C(19)H(29)NO(5), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[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 molecule is built up from...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151905/ https://www.ncbi.nlm.nih.gov/pubmed/21837209 http://dx.doi.org/10.1107/S1600536811024688 |
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author | Moumou, Mohamed Benharref, Ahmed Berraho, Moha Avignant, Daniel Oudahmane, Abdelghani Akssira, Mohamed |
author_facet | Moumou, Mohamed Benharref, Ahmed Berraho, Moha Avignant, Daniel Oudahmane, Abdelghani Akssira, Mohamed |
author_sort | Moumou, Mohamed |
collection | PubMed |
description | The title compound, C(19)H(29)NO(5), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[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 molecule is built up from two fused five- and ten-membered rings with the (pyrrolidin-4-yl)methyl group as a substituent. The two five-membered ring display the same envelope conformations, whereas the ten-membered ring adopts an approximate chair–chair conformation. The dihedral angle between the ten-membered ring and the lactone ring is 21.81 (9)°. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, intermolecular C—H⋯O interactions link the molecules into chains parallel to the c axis. |
format | Online Article Text |
id | pubmed-3151905 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-31519052011-08-11 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one Moumou, Mohamed Benharref, Ahmed Berraho, Moha Avignant, Daniel Oudahmane, Abdelghani Akssira, Mohamed Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(29)NO(5), was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[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 molecule is built up from two fused five- and ten-membered rings with the (pyrrolidin-4-yl)methyl group as a substituent. The two five-membered ring display the same envelope conformations, whereas the ten-membered ring adopts an approximate chair–chair conformation. The dihedral angle between the ten-membered ring and the lactone ring is 21.81 (9)°. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, intermolecular C—H⋯O interactions link the molecules into chains parallel to the c axis. International Union of Crystallography 2011-06-30 /pmc/articles/PMC3151905/ /pubmed/21837209 http://dx.doi.org/10.1107/S1600536811024688 Text en © Moumou et al. 2011 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 Berraho, Moha Avignant, Daniel Oudahmane, Abdelghani Akssira, Mohamed 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title | 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_full | 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_fullStr | 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_full_unstemmed | 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_short | 10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
title_sort | 10α-hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0(2,4).0(7,9)]pentadecan-14-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151905/ https://www.ncbi.nlm.nih.gov/pubmed/21837209 http://dx.doi.org/10.1107/S1600536811024688 |
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