5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one

The title compound, C(15)H(20)O(4), 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 seven-membered ring has a ch...

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Autores principales: Moumou, Mohamed, Benharref, Ahmed, Berraho, Moha, El Ammari, Lahcen, Akssira, Mohamed, Elhakmaoui, Ahmed
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/PMC3151879/
https://www.ncbi.nlm.nih.gov/pubmed/21837142
http://dx.doi.org/10.1107/S160053681102352X
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author Moumou, Mohamed
Benharref, Ahmed
Berraho, Moha
El Ammari, Lahcen
Akssira, Mohamed
Elhakmaoui, Ahmed
author_facet Moumou, Mohamed
Benharref, Ahmed
Berraho, Moha
El Ammari, Lahcen
Akssira, Mohamed
Elhakmaoui, Ahmed
author_sort Moumou, Mohamed
collection PubMed
description The title compound, C(15)H(20)O(4), 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 seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69 (10)°. In the crystal, mol­ecules are linked into chains propagating along the c axis by inter­molecular O—H⋯O hydrogen bonds; an intra­molecular O—H⋯O link also occurs.
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spelling pubmed-31518792011-08-11 5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one Moumou, Mohamed Benharref, Ahmed Berraho, Moha El Ammari, Lahcen Akssira, Mohamed Elhakmaoui, Ahmed Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(15)H(20)O(4), 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 seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69 (10)°. In the crystal, mol­ecules are linked into chains propagating along the c axis by inter­molecular O—H⋯O hydrogen bonds; an intra­molecular O—H⋯O link also occurs. International Union of Crystallography 2011-06-22 /pmc/articles/PMC3151879/ /pubmed/21837142 http://dx.doi.org/10.1107/S160053681102352X 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
Berraho, Moha
El Ammari, Lahcen
Akssira, Mohamed
Elhakmaoui, Ahmed
5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one
title 5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one
title_full 5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one
title_fullStr 5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one
title_full_unstemmed 5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one
title_short 5,9-Dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3H)-one
title_sort 5,9-dihy­droxy-9-methyl-3,6-dimethyl­ene-3a,4,5,6,6a,7,8,9,9a,9b-deca­hydro­azuleno[4,5-b]furan-2(3h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151879/
https://www.ncbi.nlm.nih.gov/pubmed/21837142
http://dx.doi.org/10.1107/S160053681102352X
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