新型脱氧胆酸类手性不对称脲分子钳的设计合成有机化学.pdfVIP

2008 年第 28 卷 有 机 化 学 Vol. 28, 2008 第 7 期, 1233～1237 Chinese Journal of Organic Chemistry No. 7, 1233～1237 ·研究论文· 新型脱氧胆酸类手性不对称脲分子钳的设计合成 赵志刚* 刘兴利 李 晖 唐晓丽 (西南民族大学化学与环境保护工程学院 成都 610041) 摘要 以刚性的脱氧胆酸甲酯为隔离基, 在其 3 位连接苯甲酰基, 12 位连接手性不对称脲, 设计合成了一类新型的手性 分子钳. 其结构均经 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良好的识别能力, 而且对 D/L-氨基酸甲酯亦具有优良的对 映选择性识别性能. 关键词 脱氧胆酸; 分子钳; 合成; 手性不对称脲 Design and Synthesis of Novel Deoxycholic Acid-Based Chiral Molecular Tweezers Containing Unsymmetrically Disubstituted Urea Unit ZHAO, Zhi-Gang* LIU, Xing-Li LI, Hui TANG, Xiao-Li (College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041) Abstract A novel type of chiral molecular tweezers has been designed and synthesized by linking benzoyl and chiral unsymmetrically disubstituted urea unit to 3-position and 12-position of rigid methyl deoxycholate. 1 Their structures were confirmed by H NMR, IR, MS spectra and elemental analyses. The recognition proper- ties of these molecular tweezers for neutral molecules and D/L-amino acid methyl esters have been investi- gated. The results indicate that these molecular tweezers not only recognize neutral organic molecules well, but also have good enantioselectivity for D/L-amino acid methyl esters. Keywords deoxycholic acid; molecular tweezer; synthesis; chiral unsymmetrical urea 分子识别是生物体内的一种基本现象, 并在生命活 性分子和手性分子的识别[6～9]. 迄今, 脱氧胆酸类手性 动中起中心作用. 利用合