新型手性不对称脲石胆酸分子裂缝的设计合成有机化学.pdfVIP

2007 年第 27 卷 有 机 化 学 Vol. 27, 2007 第 4 期, 513～518 Chinese Journal of Organic Chemistry No. 4, 513～518 ·研究论文· 新型手性不对称脲石胆酸分子裂缝的设计合成 周彩娥 赵志刚* 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 以刚性的石胆酸甲酯为骨架, 手性不对称脲为侧链, 通过三光气桥连, 设计合成了一类新型的手性分子裂缝. 7 个分子裂缝均为新化合物, 其结构均经 1H NMR, IR, MS 和元素分析确证, 并且考察了其对卤素阴离子 Cl－, Br－, I－ 的识 别性能. 初步的实验结果表明, 这类分子裂缝不仅可与所考察的卤素阴离子形成 1 ∶1 型超分子配合物, 而且对卤素阴 离子具有良好的识别选择性. 关键词 石胆酸; 分子裂缝; 合成; 手性不对称脲 Design and Synthesis of Novel Chiral Lithocholic Acid-Based Mole- cular Clefts Containing Unsymmetrically Disubstituted Urea Unit ZHOU, Cai-E ZHAO, Zhi-Gang* TANG, Xiao-Li (College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041) Abstract A novel type of chiral molecular clefts has been designed and synthesized by linking a chiral unsymmetrically disubstituted urea to rigid methyl lithocholate via triphosgene. Seven molecular clefts are 1 new compounds. Their structures were confirmed by H NMR, IR, MS spectra and elemental analyses. The recognition properties of these molecular clefts for halogen anions have been investigated by UV-visible spectral titration. The preliminary results indicated that these molecular clefts not only possessed the ability to form 1 ∶1 complex with anions examined, but also showed good selectivity for halogen anions. Keywords lithocholic acid; molecular cleft; synthesis; chiral unsymmetrical urea 分子识别是生物体系的基本特征, 酶选择性的催化 各类分子裂缝受体的设计合成及对不同底物的识别研 生化反应, 抗体与抗原的结合, 蛋白