Abstract

The title compound, C33H35NO6 [systematic name: (Z)-3-(4-{(E)-[(E)-1a,5-dimethyl-9-oxo-2,3,7,7a-tetra­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-8(1aH,6H,9H,10aH,10bH)-yl­idene]meth­yl}phen­yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­ni­trile methanol hemisolvate], C33H35NO6·0.5CH3OH, was prepared by the reaction of (Z)-3-(4-iodo­phen­yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­nitrile with parthenolide [systematic name: (E)-1a,5-dimethyl-8-methyl­ene-2,3,6,7,7a,8,10a,10b-octa­hy­dro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one] under Heck reaction conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a {4-[(Z)-2-cyano-2-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]phen­yl}methyl­idene group as a substituent. The 4-[(Z)-2-cyano-2-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]phenyl group on the parthenolide exocyclic double bond is oriented in a trans position to the lactone ring to form the E isomer. The dihedral angle between the benzene ring of the phenyl moiety and the lactone ring mean plane is 21.93 (4)°.

Document Type

Article

Publication Date

10-2014

Notes/Citation Information

Published in Acta Crystallographica Section E Structure Reports Online, v. 70, no. 10, p. o1092-o1093.

Copyright © Penthala et al. 2014

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.

Digital Object Identifier (DOI)

http://dx.doi.org/10.1107/S1600536814019333

Funding Information

This work was supported by NIH/NCI (grant No. CA158275).

Related Content

CCDC reference: 1021449

Additional supporting information: crystallographic information; 3D view; checkCIF report

e-70-o1092-sup1.cif (1186 kB)
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814019333/sj5404sup1.cif

e-70-o1092-Isup2.hkl (293 kB)
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019333/sj5404Isup2.hkl

e-70-o1092-fig1.tif (1719 kB)
A view of the mol­ecule with displacement ellipsoids drawn at the 50% probability level. DOI: 10.1107/S1600536814019333/sj5404fig1.tif

fig(1).pptx (751 kB)
Fig. 1: A view of the mol­ecule with displacement ellipsoids drawn at the 50% probability level.

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