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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (05): 747-751. 上一篇    下一篇

研究简报

L-亮氨酸衍生物手性氨基醇的合成及其对布洛芬和扁桃酸对映异构体的手性识别

刘丰良*,1，李媛媛1，王文革2，徐军1，刘言萍1，肖清波1   

  1. (1中南大学化学化工学院 长沙 410083)
    (2湖南工学院材料与化学工程系 衡阳 421002)
  • 收稿日期:2010-07-09 修回日期:2010-12-02 发布日期:2010-12-23
  • 通讯作者: 刘丰良 E-mail:lflcsu@mail.csu.edu.cn

Synthesis of Chiral Amino Alcohols from L-Leucine and Their Chiral Recognition of Enantiomers of Ibuprofen and Mandelic Acid

Liu Fengliang*,1 Li Yuanyuan1 Wang Wenge2 Xu Jun1, Liu Yanping1 Xiao Qingbo1   

  1. (1 School of Chemistry and Chemical Engineering, Central South University, Changsha 410083)
    (2 Department of Materials and Chemical Engineering, Hunan Institute of Technol-ogy, Hengyang 421002)
  • Received:2010-07-09 Revised:2010-12-02 Published:2010-12-23
  • Contact: LIU fengliang E-mail:lflcsu@mail.csu.edu.cn

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对甲基苯胺经甲基化、甲酰化得到5,N,N-三甲基-2-氨基苯甲醛|对L-亮氨酸经酯化、格氏反应得到二齿手性氨基醇. 二齿手性氨基醇与上述醛经缩合、还原反应, 得到三齿手性氨基醇. 产物结构经IR, MS和1H NMR等进行了表征|通过改变主客体的浓度及手性羧酸的纯度, 运用1H NMR分别考察了主体二齿手性氨基醇、三齿手性氨基醇对客体布洛芬和扁桃酸对映异构体的手性识别能力. 结果表明: 当主客体物质的量之比为1∶1时, 三齿手性氨基醇对布洛芬消旋体的α位甲基质子及扁桃酸消旋体的α位质子分别产生11.2和9.2 Hz的化学位移差值.

关键词: L-亮氨酸, 手性氨基醇, 三齿配体, 手性识别, 布洛芬, 扁桃酸, 对映异构体

Chiral amino alcohol polydentate ligand was derived from 5,N,N-tri-methyl-2-amino benzaldehyde and chiral amino alcohol by condensation and reduction. Thus the former was obtained by methylation and formylation of p-methyl aniline, the latter was prepared by esterification and Grignard reaction of L-leucine. The products were characterized by IR, 1H NMR and MS techniques. The chiral amino alcohol and the chiral amino alcohol polydentate ligand were evaluated as chiral solvating agent for chiral carboxylic acid such as ibuprofen and mandelic acid. In the presence of an equimolar amount of guest and host, the chemical shift non-equivalences (ΔΔδ) of the methyl proton of (CH3)CHCOOH in racemic ibuprofen and α-H in racemic mandelic acid are 11.2 and 9.2 Hz, respectively.

Key words: L-leucine, chiral amino alcohol, polydentate ligand, chiral recognition, mandelic acid, ibupro-fen, enantiomer