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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (06): 860-865. 上一篇    下一篇

研究简报

系列单取代烷氧基-2-羟丙基-β-环糊精的合成与表征

张毅民*，张国栋，甘永江，苑珊，王虹   

  1. (天津大学化工学院 绿色合成与转化教育部重点实验室 天津 300072)
  • 收稿日期:2005-07-07 修回日期:2005-12-26 发布日期:2006-05-31
  • 通讯作者: 张毅民

Synthesis and Characterization of Monosubstituted 3-Alkyloxy-2-hydroxypropyl-β-cyclodextrins

ZHANG Yi-Min*,ZHANG Guo-Dong,GAN Yong-Jiang
YUAN Shan,WANG Hong   

  1. (Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072)
  • Received:2005-07-07 Revised:2005-12-26 Published:2006-05-31
  • Contact: ZHANG Yi-Min

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以环氧氯丙烷和脂肪醇为原料, 通过相转移催化法合成了乙基、正丙基、正丁基和正戊基缩水甘油醚(1～4), 并利用所合成的缩水甘油醚和β-环糊精为原料, 分别在弱碱水溶液(1.5%)和强碱水溶液(30%)中制备并用硅胶柱分离出单2位取代的乙氧基、丙氧基、丁氧基和戊氧基-2-羟丙基-β-环糊精(1a～4a)和单6位取代的丙氧基、丁氧基和戊氧基-2-羟丙基-β-环糊精(2b～4b), 利用薄层色谱、红外光谱、差热扫描量热分析、质谱和核磁共振等手段对所合成的产品进行了表征.

关键词: β-环糊精衍生物, 缩水甘油醚, 烷氧基-2-羟丙基-β-环糊精, 环氧氯丙烷

Four intermediates of glycidyl ethers, namely ethyl glycidyl ether (1), propyl glycidyl ether (2), butyl glycidyl ether (3) and amyl glycidyl ether (4), were obtained through a phase-transfer catalytic methodology using acyclic alcohol and epichlorohydrin as raw materials. To choose 1.5% or 30% of sodium hydroxide solution as the environmental media, subsequent procedures were conducted with these glycidyl ethers and β-cyclodextrin. The products were isolated through a self packed silica gel column chromatography, and their chemical structures were proved to be the mono substituted 2-(3-alkyloxy-2-hydroxypropyl)- β-cyclodextrins (1a～4a) and mono substituted 6-(3-alkyloxy-2-hydroxypropyl)-β-cyclodextrins (2b～4b) by means of the TLC, IR, DSC, MS, 1H NMR and 13C NMR measurements.

Key words: glycidyl ether, epichlorohydrin, 3-alkyloxy-2-hydroxypropyl-β- cyclodextrin, β-cyclodextrin derivative