(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one

The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-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 f...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, Daran, Jean-Claude, Elhakmaoui, Ahmed, Akssira, Mohamed, Berraho, Moha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247566/
https://www.ncbi.nlm.nih.gov/pubmed/22219871
http://dx.doi.org/10.1107/S1600536811039717
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author Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Elhakmaoui, Ahmed
Akssira, Mohamed
Berraho, Moha
author_facet Moumou, Mohamed
Benharref, Ahmed
Daran, Jean-Claude
Elhakmaoui, Ahmed
Akssira, Mohamed
Berraho, Moha
author_sort Moumou, Mohamed
collection PubMed
description The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-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. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the two rings is 66.4 (2)°. In the crystal, mol­ecules are linked into chains propagating along the a axis by O—H⋯O hydrogen bonds.
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spelling pubmed-32475662012-01-04 (1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one Moumou, Mohamed Benharref, Ahmed Daran, Jean-Claude Elhakmaoui, Ahmed Akssira, Mohamed Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-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. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the two rings is 66.4 (2)°. In the crystal, mol­ecules are linked into chains propagating along the a axis by O—H⋯O hydrogen bonds. International Union of Crystallography 2011-10-05 /pmc/articles/PMC3247566/ /pubmed/22219871 http://dx.doi.org/10.1107/S1600536811039717 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
Akssira, Mohamed
Berraho, Moha
(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
title (1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
title_full (1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
title_fullStr (1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
title_full_unstemmed (1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
title_short (1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
title_sort (1s,2r,3r,8r,10s)-3-chloro-2,8-dihy­droxy-3,7-dimethyl-11-methyl­idene-13-oxabicyclo­[8.3.0]tridec-6-en-12-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247566/
https://www.ncbi.nlm.nih.gov/pubmed/22219871
http://dx.doi.org/10.1107/S1600536811039717
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