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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (06): 772-777. 上一篇    下一篇

研究论文

微波促进一锅法合成氨基甲酸酯型α-猪去氧胆酸分子钳

刘兴利a，赵志刚*,a，陈淑华b   

  1. (a西南民族大学化学与环境保护工程学院 成都 610041)
    (b四川大学化学学院 成都 610064)
  • 收稿日期:2006-11-21 修回日期:2007-03-28 发布日期:2007-05-21
  • 通讯作者: 赵志刚

Microwave Assisted One-Pot Synthesis of Carbamate-Type Molecular Tweezers Based on α-Hyodeoxycholic Acid

LIU Xing-Lia, ZHAO Zhi-Gang*,a, CHEN Shu-Huab   

  1. (a College of Chemistry and Environmental Protection Engineering, Southwest University for Nation-alities, Chengdu 610041)
    (b Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2006-11-21 Revised:2007-03-28 Published:2007-05-21
  • Contact: ZHAO Zhi-Gang

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在微波辐射条件下, 以α-猪去氧胆酸为隔离基, 通过三光气桥连各种芳香胺, 以很好的产率合成了一系列新的手性分子钳, 其结构经1H NMR, IR, MS和元素分析确证, 并且考察了其对中性分子和D/L-氨基酸甲酯的识别性能. 实验结果表明, 这类分子钳人工受体不仅对中性有机小分子具有优良的识别性能, 而且对D/L-氨基酸甲酯亦具有良好的对映选择性识别能力.

关键词: 一锅法合成, α-猪去氧胆酸, 分子钳, 微波辐射

A series of new chiral molecular tweezers were synthesized in excellent yields by using α-hyodeoxycholic acid as spacer to bridge different aromatic amines via triphosgene under mi-crowave irradiation. Their structures were characterized by 1H NMR, IR, MS spectra and ele-mental analysis. The recognition properties of these molecular tweezers for neutral molecules and D/L-amino acid methyl esters were investigated. The results indicate that these molecular tweezers not only recognize neutral organic molecules but also have good enantioselectivity for D/L-methyl esters of amino acids.

Key words: one-pot synthesis, α-hyodeoxycholic acid, molecular tweezer, microwave irradiation