Crystal Structure of (E)-13-{4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}parthenolide methanol hemisolvate

Authors

Narsimha Reddy Penthala, University of Arkansas
Shobanbabu Bommagani, University of Arkansas
Venumadhav Janganati, University of Arkansas
Sean Parkin, University of KentuckyFollow
Peter A. Crooks, University of ArkansasFollow

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: Crystallographic Communications, v. 70, part 10, p. o1092-o1093.

This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Digital Object Identifier (DOI)

https://doi.org/10.1107/S1600536814019333

Funding Information

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

Related Content

Supporting information for this paper is available from the IUCr electronic archives (Reference: SJ5404).

CCDC reference: 1021449

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814019333/sj5404sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019333/sj5404Isup2.hkl

checkCIF report

3D view of crystallographic information

Repository Citation

Penthala, Narsimha Reddy; Bommagani, Shobanbabu; Janganati, Venumadhav; Parkin, Sean; and Crooks, Peter A., "Crystal Structure of (E)-13-{4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}parthenolide methanol hemisolvate" (2014). Chemistry Faculty Publications. 30.
https://uknowledge.uky.edu/chemistry_facpub/30