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3-苯亚甲基-2-吲哚酮衍生物几何异构体的合成分离与NMR分析
引用本文:李凌宇,施伦勇,梁鸿,张庆英.3-苯亚甲基-2-吲哚酮衍生物几何异构体的合成分离与NMR分析[J].中国药学,2014,23(12):858-865.
作者姓名:李凌宇  施伦勇  梁鸿  张庆英
作者单位:北京大学医学部药学院天然药物及仿生药物国家重点实验室;天然药物学系,北京100191
基金项目:National Natural Science Foundation of China(Grant No.21172008 and 21372015) Acknowledgements This project was financially supported by National Natural Science Foundation of China (Grant No. 21172008 and 21372015).
摘    要:本文合成了一系列3-(4'-取代苯亚甲基)-2-吲哚酮的E和Z几何异构体,并采用反相硅胶色谱的方法首次对所有异构体进行了成功分离。通过对E和Z异构体1H NMR特征的分析发现了E和Z异构体中处于取代苯环屏蔽区的质子实际受到较明显去屏蔽效应的反常现象并对这种现象进行了分析。

关 键 词:3-苯亚甲基-2-吲哚酮  几何异构体  去屏蔽现象  NMR分析
收稿时间:2014-05-28

Synthesis,separation and NMR analysis of geometrical isomers of 3-benzylidene-indolin-2-one derivatives
Lingyu Li,Lunyong Shi,Hong Liang,Qingying Zhang.Synthesis,separation and NMR analysis of geometrical isomers of 3-benzylidene-indolin-2-one derivatives[J].Journal of Chinese Pharmaceutical Sciences,2014,23(12):858-865.
Authors:Lingyu Li  Lunyong Shi  Hong Liang  Qingying Zhang
Institution:( State Key Laboratory of Natural and Biomimetic Drugs and Department of Natural Medicines, School of Pharmaceutical Sciences Peking University Health Science Center, Beijing 100191, China)
Abstract:A series of E and Z-isomers of 3-(4'-substituted benzylidene)-indolin-2-one derivatives were synthesized and separated. Based on their 1H NMR characterization, an unusual counterintuitive deshielding phenomenon for the protons presenting in the shielding zone of phenyl ring was observed and analyzed for the first time.
Keywords:3-Benzylidene-indolin-2-one  Geometrical isomers  Deshielding phenomenon  NMR analysis
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