Abstract
The title compound, C19H22N2O3, {systematic name (1aR,4E,7aS,8E,10aS,10bR)-1a,5-dimethyl-8-[(pyrimidin-5-yl)methylidene]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one} was obtained from the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bR,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] with 5-bromopyrimidine under Heck reaction conditions, and was identified as an E isomer. The molecule possesses ten-, five- (lactone) and three-membered (epoxide) rings with a pyrimidine group as a substituent. The ten-membered ring displays an approximate chair–chair conformation, while the lactone ring shows a flattened envelope-type conformation. The dihedral angle between the pyrimidine moiety and the lactone ring system is 29.43 (7)°.
Document Type
Article
Publication Date
12-2015
Digital Object Identifier (DOI)
https://doi.org/10.1107/S2056989015021507
Funding Information
This work was supported by NIH/NCI grant CA158275.
Related Content
CCDC reference: 1436825
Crystal structure: contains datablocks I, global. DOI: https://doi.org//10.1107/S2056989015021507/zs2350sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org//10.1107/S2056989015021507/zs2350Isup2.hkl
3D view of crystallographic information
Repository Citation
Bommagani, Shobanbabu; Penthala, Narsimha Reddy; Parkin, Sean; and Crooks, Peter A., "Crystal Structure of (E)-13-(pyrimidin-5-yl)parthenolide" (2015). Chemistry Faculty Publications. 63.
https://uknowledge.uky.edu/chemistry_facpub/63
PowerPoint slides
zs2350sup1.cif (350 kB)
Crystal structure: contains datablocks I, global.
zs2350Isup2.hkl (165 kB)
Structure factors: contains datablock I.
Notes/Citation Information
Published by Acta Crystallographica Section E: Crystallographic Communications, v. 71, part 12, p. 1536-1538.
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.