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13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate

The title compound, C(18)H(24)N(2)O(4)·H(2)O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hy­droxy­methyl-8-[(1H-imidazol-1-yl)meth­yl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synt...

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Autores principales: Janganati, Venumadhav, Penthala, Narsimha Reddy, Parkin, Sean, Crooks, Peter A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3885019/
https://www.ncbi.nlm.nih.gov/pubmed/24454194
http://dx.doi.org/10.1107/S1600536813029188
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author Janganati, Venumadhav
Penthala, Narsimha Reddy
Parkin, Sean
Crooks, Peter A.
author_facet Janganati, Venumadhav
Penthala, Narsimha Reddy
Parkin, Sean
Crooks, Peter A.
author_sort Janganati, Venumadhav
collection PubMed
description The title compound, C(18)H(24)N(2)O(4)·H(2)O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hy­droxy­methyl-8-[(1H-imidazol-1-yl)meth­yl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synthesized under Michael addition conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The inter­nal double bond of the ten-membered ring identifies it as the cis or E isomer. The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonds link the mol­ecules (along with water) into sheets parallel to the bc plane.
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spelling pubmed-38850192014-01-17 13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate Janganati, Venumadhav Penthala, Narsimha Reddy Parkin, Sean Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(24)N(2)O(4)·H(2)O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hy­droxy­methyl-8-[(1H-imidazol-1-yl)meth­yl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synthesized under Michael addition conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The inter­nal double bond of the ten-membered ring identifies it as the cis or E isomer. The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonds link the mol­ecules (along with water) into sheets parallel to the bc plane. International Union of Crystallography 2013-11-06 /pmc/articles/PMC3885019/ /pubmed/24454194 http://dx.doi.org/10.1107/S1600536813029188 Text en © Janganati et al. 2013 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
Janganati, Venumadhav
Penthala, Narsimha Reddy
Parkin, Sean
Crooks, Peter A.
13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate
title 13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate
title_full 13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate
title_fullStr 13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate
title_full_unstemmed 13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate
title_short 13-(Imidazol-1-yl)-11,13-di­hydro­melampomagnolide B monohydrate
title_sort 13-(imidazol-1-yl)-11,13-di­hydro­melampomagnolide b monohydrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3885019/
https://www.ncbi.nlm.nih.gov/pubmed/24454194
http://dx.doi.org/10.1107/S1600536813029188
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