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9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one

The title compound, C(20)H(31)NO(4), 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 mol­ecule is built up from f...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, Daran, Jean-Claude, Elhakmaoui, Ahmed, Berraho, Moha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201218/
https://www.ncbi.nlm.nih.gov/pubmed/22058816
http://dx.doi.org/10.1107/S1600536811038803
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author Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Elhakmaoui, Ahmed
Berraho, Moha
author_facet Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Elhakmaoui, Ahmed
Berraho, Moha
author_sort Moumou, Mohamed
collection PubMed
description The title compound, C(20)H(31)NO(4), 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 mol­ecule is built up from fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)–C–C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7 (4)°. The mol­ecular conformation is stabilized by an O—H⋯N hydrogen bond and the crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions.
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spelling pubmed-32012182011-11-06 9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one Moumou, Mohamed Benharref, Ahmed Daran, Jean-Claude Elhakmaoui, Ahmed Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(20)H(31)NO(4), 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 mol­ecule is built up from fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)–C–C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7 (4)°. The mol­ecular conformation is stabilized by an O—H⋯N hydrogen bond and the crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions. International Union of Crystallography 2011-09-30 /pmc/articles/PMC3201218/ /pubmed/22058816 http://dx.doi.org/10.1107/S1600536811038803 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
Daran, Jean-Claude
Elhakmaoui, Ahmed
Berraho, Moha
9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title 9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_full 9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_fullStr 9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_full_unstemmed 9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_short 9-Hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
title_sort 9-hy­droxy-4,8-dimethyl-12-(piperidin-1-ylmeth­yl)-3,14-dioxatricyclo­[9.3.0.0(2,4)]tetra­dec-7-en-13-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201218/
https://www.ncbi.nlm.nih.gov/pubmed/22058816
http://dx.doi.org/10.1107/S1600536811038803
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