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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (08): 1022-1026. 上一篇    下一篇

研究简报

系列缩水甘油醚类β-环糊精衍生物的合成及结构表征

张毅民*，陈春凤，孙聪善，李潇   

  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:2006-09-26 修回日期:1900-01-01 发布日期:2007-07-30
  • 通讯作者: 张毅民*

Synthesis and Characterization of Glycidyl Ether Modified β-Cyclodextrin Derivatives

ZHANG Yi-Min*, CHEN Chun-Feng, SUN Cong-Shan, LI Xiao   

  1. (Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072)
  • Received:2006-09-26 Revised:1900-01-01 Published:2007-07-30
  • Contact: ZHANG Yi-Min*

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1121

被引次数

10 | 5

以苯基缩水甘油醚、邻甲基酚缩水甘油醚及苯甲基缩水甘油醚(1～3)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%)中制备出系列缩水甘油醚类β-环糊精衍生物, 所得产物用自制硅胶色谱柱分离, 以V(正丙醇)∶V(水)∶V(浓氨水)＝6∶3∶1作为硅胶色谱柱分离纯化的洗脱剂, 得到单2位取代的苯氧基(或邻甲基苯氧基或苯甲氧基-2-羟丙基-β-环糊精(1a～3a)和单6位取代的苯氧基(或邻甲基苯氧基)-2-羟丙基-β-环糊精(1b～2b). 所得产品用薄层色谱、红外光谱、质谱和核磁共振波谱等手段进行了表征.

关键词: β-环糊精, 核磁共振波谱, 缩水甘油醚, 质谱, 薄层色谱

Using phenyl glycidyl ether (1), 2-methylphenyl glycidyl ether (2), benzyl glycidyl ether (3) and β-cyclodextrin as raw materials, in 1.5% (m/V) and 30% (m/V) sodium hydroxide solution, novel β-cyclodextrin derivatives have been synthesized. The products were isolated by using proper eluent V(1-propanol)∶V(water)∶V(concd aq ammonia)＝6∶3∶1 through a self packed silica gel column chro-matography, and their chemical structures were proved to be mono 2-substituted phenoxy (or 2-methylphenoxy or benzyloxy)-2-hydroxypropyl-β-cyclodextrin (1a～3a) and mono 6-substituted phenoxy (or 2-methylphenoxy)-2-hydroxypropyl-β-cyclodextrin (1b～2b) by means of TLC, IR, MS, 1H NMR and 13C NMR spectra.

Key words: mass spectrometry, glycidyl ether, nuclear magnetic resonance spectroscopy, thin-layer chromatography (TLC), β-cyclodextrin