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10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-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(34)N(2)O(6), 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 ten-membered ring adopts...

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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/PMC3344453/
https://www.ncbi.nlm.nih.gov/pubmed/22590215
http://dx.doi.org/10.1107/S1600536812013876
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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(34)N(2)O(6), 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 ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is stabilized by an O—H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C—H⋯O inter­actions.
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spelling pubmed-33444532012-05-15 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-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(34)N(2)O(6), 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 ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hy­droxy group forming the flap. The mol­ecular conformation is stabilized by an O—H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C—H⋯O inter­actions. International Union of Crystallography 2012-04-06 /pmc/articles/PMC3344453/ /pubmed/22590215 http://dx.doi.org/10.1107/S1600536812013876 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
10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_full 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_fullStr 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_full_unstemmed 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_short 10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.0(2,4).0(7,9)]penta­decan-14-one
title_sort 10α-hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-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/PMC3344453/
https://www.ncbi.nlm.nih.gov/pubmed/22590215
http://dx.doi.org/10.1107/S1600536812013876
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