邻氯扁桃酸的拆分研究 Ⅱ.机理分析  

Resolution of o-Chloromandelic Acid Ⅱ.Mechanism Analysis

作　　者：彭阳峰[1] 何佺[2] 皇甫平燕[1] 吴福忠[1] 徐智胜 

机构地区：[1]华东理工大学化工学院,上海200237 [2]宁波高等专科学校化工系,宁波315016 [3]浙江九洲药业股份有限公司,浙江台州318000

出　　处：《华东理工大学学报（自然科学版）》2004年第4期375-378,共4页Journal of East China University of Science and Technology

基　　金：宁波市青年基金(2003A62006)

摘　　要：在苯乙胺(PEA)、N-苄基苯乙胺(BPA)、1-(p-硝基苯基)-2-氨基-1,3-丙二醇(SA)拆分邻氯扁桃酸(oClMA)的实验基础上,运用三点作用模型,结合NMR分析,探讨了氢键、空间位阻等在拆分过程中的作用,讨论了PEA、BPA、SA拆分oClMA的特性,说明成盐键力是拆分剂与oClMA成盐的基础、非对映体盐间氢键的存在对拆分起关键作用、非对映体盐间的多点性作用也很重要,一定程度上弥补了由于其他原因造成的较弱的氢键作用。Based on the resolution experiment of o-chloromandelic acid(oClMA) by α-phenethylamine(PEA), N-benzyl-α-phenethylamine(BPA) and threo-1-(4-nitrophenyl)-2-amino-1,3-propanediol(SA), mechanism of resolution process of oClMA by PEA, BPA and SA was analyzed with three point interaction model and NMR data. Salt linkage bond was proved to be the foundation for this diastereoisomeric salt formation process. Hydrogen bond was also found playing a key role in differentiating these two (diastereoisomeric) salts. To certain extend, the relatively weak hydrogen bonds is made up for by multi-point force.

关 键 词：邻氯扁桃酸 三点作用模型 氢键 空间位阻 成盐键力 

分 类 号：O621.14[理学—有机化学]