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9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one

The title compound, C(15)H(18)O(3), 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 seven-membered ring of the ti...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, Daran, Jean Claude, Mellouki, Fouad, 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/PMC3275063/
https://www.ncbi.nlm.nih.gov/pubmed/22347008
http://dx.doi.org/10.1107/S1600536812000165
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author Moumou, Mohamed
Benharref, Ahmed
Daran, Jean Claude
Mellouki, Fouad
Berraho, Moha
author_facet Moumou, Mohamed
Benharref, Ahmed
Daran, Jean Claude
Mellouki, Fouad
Berraho, Moha
author_sort Moumou, Mohamed
collection PubMed
description The title compound, C(15)H(18)O(3), 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 seven-membered ring of the title compound shows a chair conformation, while the five-membered rings exibit different conformations, viz a twisted one for the lactone ring and an envelope conformation for the other five-membered ring with the C atom closest to the hydroxy group forming the flap. In the crystal, O—H⋯O hydrogen bonds connect mol­ecules into dimers that are inter­connected by C—H⋯O inter­actions, producing supramolecular chains along the b axis.
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spelling pubmed-32750632012-02-15 9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one Moumou, Mohamed Benharref, Ahmed Daran, Jean Claude Mellouki, Fouad Berraho, Moha Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(15)H(18)O(3), 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 seven-membered ring of the title compound shows a chair conformation, while the five-membered rings exibit different conformations, viz a twisted one for the lactone ring and an envelope conformation for the other five-membered ring with the C atom closest to the hydroxy group forming the flap. In the crystal, O—H⋯O hydrogen bonds connect mol­ecules into dimers that are inter­connected by C—H⋯O inter­actions, producing supramolecular chains along the b axis. International Union of Crystallography 2012-01-14 /pmc/articles/PMC3275063/ /pubmed/22347008 http://dx.doi.org/10.1107/S1600536812000165 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
Daran, Jean Claude
Mellouki, Fouad
Berraho, Moha
9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one
title 9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one
title_full 9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one
title_fullStr 9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one
title_full_unstemmed 9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one
title_short 9β-Hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3H)-one
title_sort 9β-hy­droxy-6,9-dimethyl-3-methyl­ene-3a,4,8,9,9a,9b-hexa­hydro­azuleno[4,5-b]furan-2(3h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3275063/
https://www.ncbi.nlm.nih.gov/pubmed/22347008
http://dx.doi.org/10.1107/S1600536812000165
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