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α-氯代桂皮酰胺类化合物的合成与其构型的确定
Synthesis and Configurational Assignment of α-Chlorocinnamamides
【摘要】 <正> 改变苯环取代基(X)及酰胺氮上的取代基(R)研究桂皮酰胺类化合物与抗惊作用的关系已有一些报道,Balsamo 等发现 E 和 Z-
【Abstract】 Six pairs of geometric isomers of α-chlorocinnamamides were synthesized.Theirconfigurations were assigned on the basis of their UV λmaxand the 1H NMR chemical shiftsof protons on the amide and olefinic bond.The tetrasubstitution on the double bond drasti-cally prevents the coplanarity of the benzene ring with the double bond in the Z and in theE form.But the influence is smaller in the Z form than in the E isomer.So the value ofλmax of Z form is larger than E form.The diamagnetic anisotropy of the aromatic ring couldbe one of the causes of the relatively higher chemical shifts of the β-H and NH.
【基金】 国家自然科学基金
- 【文献出处】 有机化学 ,Chinese Journal of Organic cHEMISTRY , 编辑部邮箱 ,1988年03期
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