高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (6): 1031.

• 研究简报 • 上一篇    下一篇

手性高效液相色谱拆分3-取代异吲哚-1-酮的研究

阮源萍1,2, 徐秀青1,2, 贺明珠1, 周香1, 黄培强1   

  1. 1. 厦门大学化学系;
    2. 厦门大学现代分析科学教育部重点实验室, 厦门 361005
  • 收稿日期:2003-08-18 出版日期:2004-06-24 发布日期:2004-06-24
  • 通讯作者: 黄培强(1962年出生),男,博士,教授,博士生导师,从事不对称合成研究.E-mail:pqhuang@xmu.edu.cn E-mail:pqhuang@xmu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:20072031,20270048和203900505)资助

Enantioseparation of 3-Substituted Isoindolin-1-ones by HPLC

RUAN Yuan-Ping1,2, XU Xiu-Qing1,2, HE Ming-Zhu1, ZHOU Xiang1, HUANG Pei-Qiang1   

  1. 1. Department of Chemistry;
    2. The Key Laboratory of Analytical Science of Ministry of Education, Xiamen University, Xiamen 361005, China
  • Received:2003-08-18 Online:2004-06-24 Published:2004-06-24

摘要: 从伏牛花类植物中提取的生物碱Lennoxam ine[1]、Nuevam ine和Chilenine,新研发的抗焦虑药Paz-inaclone[2]和Pagoclone[3]以及利尿、抗高血压药Chlortalidone[4]等均含有光活性3-取代异吲哚-1-酮(2,3-二氢-1H -异吲哚-1-酮).这类化合物还是一类新型的不对称合成手性辅助基[5].因此,光学纯的3-取代异吲哚-1-酮化合物在药物研发和不对称合成等领域具有应用前景.但有关它们的色谱拆分少见报道[6,7].本文对15个外消旋3-取代异吲哚-1-酮样品进行高效液相色谱拆分研究,通过建立的手性色谱方法,不仅准确测定了相关产物的光学纯度,而且确认了N -取代邻苯二甲酰亚胺上手性辅助基在不对称合成过程[8]中未发生消旋化.同时探讨了样品中3-位取代基对手性拆分的影响.

关键词: 3-取代异吲哚-1-酮, 对映体拆分, 高效液相色谱, 手性固定相

Abstract: The enantioseparation of 3-alkyl-isoindolin-1-ones(1—9) and 3-alkyl-3-hydroxy-isoindolin-1-ones(10—14)(R=Me,Et,n-Pr,n-Bu,n-C5H11 ,n-C7H15 ,i-Bu,Ph and Bn),as well as 3-n-heptyl-2-[2-hydroxy-1-phenylethyl]-isoindolin-1-one(15) by HPLC using (S)-tert-leucine and (S)-1-α-NEA as a chiral stationary phase,and 1%—6%(volume fraction) 2-propanol or ethanol in hexane as the mobile phase was studied. The effect of content of polar solvent in mobile phase on the enantioseparation was discussed. The effects of 3-substituents on retention factor and chiral recognition were studied. For the majority of racemates(1—14),a baseline separation could be obtained. For racemate(15),the elution orders are (3R,1′R)/(3S,1′S) then (3R,1′S)/(3S,1′R) with n-hexane/2-propanol(volume ratio 99∶1) as a mobile phase and the resolutions are 1.44 and 5.58,respectively.

Key words: 3-Substituted isoindolin-1-one, Enantioseparation, High performance liquid chromatography(HPLC), Chiral stationary phase

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