Bommagani Shobanbabu, Penthala Narsihma R, Parkin Sean, Crooks Peter A
Dept. of Pharm. Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Dept. of Chemistry, University of Kentucky, Lexington KY 40506, USA.
Acta Crystallogr E Crystallogr Commun. 2018 Oct 9;74(Pt 11):1543-1546. doi: 10.1107/S2056989018013622. eCollection 2018 Nov 1.
The title compound, CHNO [systematic name: (1a,4,7a,8,10a,10b)-8-(2-amino-benzyl-idene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-]furan-9(1a)-one], was synthesized by the reaction of parthenolide [systematic name (1a,7a,10a,10b,)-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-]furan-9(1a)-one] with 2-iodo-aniline Heck reaction conditions. The mol-ecule is composed of fused ten-, five- (lactone), and three-membered (epoxide) rings. The lactone ring shows a flattened envelope-type conformation (r.m.s. deviation from planarity = 0.0477 Å), and bears a 2-amino-benzyl-idene substituent that is disordered over two conformations [occupancy factors 0.901 (4) and 0.099 (4)]. The ten-membered ring has an approximate chair-chair conformation. The dihedral angle between the 2-amino-benzyl-idine moiety (major component) and the lactone ring (mean plane) is 59.93 (7)°. There are no conventional hydrogen bonds, but there are a number of weaker C-H⋯O-type inter-actions.
标题化合物CHNO [系统名称：(1a,4,7a,8,10a,10b)-8-(2-氨基-亚苄基)-1a,5-二甲基-2,3,6,7,7a,8,10a,10b-八氢-环氧乙烷并[2',3':9,10]环癸烷-[1,2-]呋喃-9(1a)-酮] 通过倍半萜内酯 [系统名称(1a,7a,10a,10b,)-1a,5-二甲基-8-亚甲基-2,3,6,7,7a,8,10,10b-八氢-环氧乙烷并[2',3':9,10]环癸烷-[1,2-]呋喃-9(1a)-酮] 与2-碘苯胺在Heck反应条件下反应合成。该分子由稠合的十元、五元（内酯）和三元（环氧化物）环组成。内酯环呈现扁平信封型构象（与平面的均方根偏差 = 0.0477 Å），并带有一个2-氨基-亚苄基取代基，该取代基在两种构象上无序 [占有率因子分别为0.901 (4) 和0.099 (4)]。十元环具有近似椅式-椅式构象。2-氨基-亚苄基部分（主要成分）与内酯环（平均平面）之间的二面角为59.93 (7)°。不存在传统氢键，但存在许多较弱的C-H⋯O型相互作用。
