核磁共振氢谱中二苯基乙二胺衍生物手性识别其结构类似物（英文）  

Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy

作　　者：杨盈[2] 黄少华 冯继文[3] YANG Ying;HUANG Shao-hua;FENG Ji-wen(Institute of Drug Discovery and Technology,Ningbo University,Ningbo 315211,China;Qingdao Institute of Bioenergy and Bioprocess Technology,Chinese Academy of Sciences,Qingdao 266101,China;State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics,Wuhan Institute of Physics and Mathematics,Chinese Academy of Sciences,Wuhan 430071,China)

机构地区：[1]宁波大学新药技术研究院,浙江宁波315211 [2]中国科学院青岛生物能源与过程研究所,山东青岛266101 [3]波谱与原子分子物理国家重点实验室,中国科学院武汉物理与数学研究所,湖北武汉430071

出　　处：《波谱学杂志》2019年第4期525-533,共9页Chinese Journal of Magnetic Resonance

基　　金：the National Natural Science Foundation of China(21105108);the Key Technology Talent Program of Chinese Academy of Sciences(2015)

摘　　要：本文通过手性二苯基乙二胺与异氰酸酯的衍生化反应,合成了一种C2对称的手性主体1.该主体可以手性识别其结构类似物:α-苯乙胺(客体2)、α-对甲氧基苯乙胺(客体9)以及它们的衍生物(客体3~8和10~13).高分辨核磁共振氢谱(1H NMR)显示了对映体识别中主客体间的氢键作用.结果表明,除含2个NO2的客体7和12外,主体1可以较易识别含有两个伯胺的脲和酰胺衍生物.研究还发现,主体1对脲衍生物2、9比对酰胺衍生物有更强的氢键作用,此外主体1对(R)和(S)-脲衍生物中的CHCH3基团也有更高的辨识能力.A C2-symmetric host(host 1)was synthesized by derivatization of chiral diphenylethylenediamine with phenylisocyanate.High-resolution proton nuclear magnetic resonance(1H NMR)was used to investigate whether the chiral host could be used for enantiomeric discrimination of its structural analogues:α-phenylethylamine(guest 2),α-(p-methoxyphenyl)ethylamine(guest 9)and their derivatives(guests 3~8 and 10~13),and hydrogen-bonding interactions underlying the enantiomeric discrimination.It was observed that the host was able to recognize the urea and amide derivatives of the two primary amines,except for guests 7 and 12 bearing two NO2 groups.The host had stronger hydrogen-bonding interactions with the urea derivatives of guests 2 and 9 than with the corresponding amide derivatives,and high enantiomeric discrimination ability for the CHCH3 groups of the(R)-and(S)-urea derivatives.

关 键 词：二苯基乙二胺 衍生物 对映体识别 核磁共振(NMR)波谱 

分 类 号：O482.53[理学—固体物理]