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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...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, Berraho, Moha, Avignant, Daniel, Oudahmane, Abdelghani, Akssira, Mohamed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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.
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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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