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(1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one

The title compound, C(25)H(33)ClN(2)O(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...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, El Ammari, Lahcen, Adil, Mina, Berraho, Moha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344091/
https://www.ncbi.nlm.nih.gov/pubmed/22606094
http://dx.doi.org/10.1107/S1600536812011816
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author Moumou, Mohamed
Benharref, Ahmed
El Ammari, Lahcen
Adil, Mina
Berraho, Moha
author_facet Moumou, Mohamed
Benharref, Ahmed
El Ammari, Lahcen
Adil, Mina
Berraho, Moha
author_sort Moumou, Mohamed
collection PubMed
description The title compound, C(25)H(33)ClN(2)O(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 fused five- and ten-membered rings with two additional ep­oxy ring systems and a chloro­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond between the hy­droxy group and a piperazine N atom. The crystal structure is stabilized by weak C—H⋯O inter­actions.
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spelling pubmed-33440912012-05-17 (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one Moumou, Mohamed Benharref, Ahmed El Ammari, Lahcen Adil, Mina Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(25)H(33)ClN(2)O(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 fused five- and ten-membered rings with two additional ep­oxy ring systems and a chloro­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond between the hy­droxy group and a piperazine N atom. The crystal structure is stabilized by weak C—H⋯O inter­actions. International Union of Crystallography 2012-03-24 /pmc/articles/PMC3344091/ /pubmed/22606094 http://dx.doi.org/10.1107/S1600536812011816 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
El Ammari, Lahcen
Adil, Mina
Berraho, Moha
(1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_full (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_fullStr (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_full_unstemmed (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_short (1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_sort (1s,2r,3r,6r,7s,8r,10s,11s)-13-{[4-(4-chloro­phen­yl)piperazin-1-yl]meth­yl}-10-hy­droxy-4,9-dimethyl-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/PMC3344091/
https://www.ncbi.nlm.nih.gov/pubmed/22606094
http://dx.doi.org/10.1107/S1600536812011816
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