有机化学 ›› 2010, Vol. 30 ›› Issue (08): 1212-1219. 上一篇    下一篇

研究论文

新型醚键连接的杂环功能基杯[4]芳烃衍生物的合成及结构

赵邦屯*,1,王成斌2,吴圣江2,冶保献*,2   

  1. (1洛阳师范学院化学系 洛阳 471022)
    (2郑州大学化学系 郑州 450001)
  • 收稿日期:2010-02-10 修回日期:2010-04-11 发布日期:2010-05-14
  • 通讯作者: 赵邦屯 E-mail:zbt@lynu.edu.cn
  • 基金资助:

    新型电化学调控的杯芳烃-四硫富瓦烯超分子体系的构筑及功能研究

Synthesis and Structures of p-tert-Butylcalix[4]arene Derivatives Containing Heterocycle Functional Groups Tethered by Ether Bridges

Zhao Bangtun*,1 Wang Chengbin2 Wu Shengji-ang2 Ye Baoxian*,2   

  1. (1 Department of Chemistry, Luoyang Normal University, Luoyang 471022)
    (2 Department of Chemistry, Zhengzhou University, Zhengzhou 450001)
  • Received:2010-02-10 Revised:2010-04-11 Published:2010-05-14

以碘化钠为催化剂, 在氢氧化钠存在下2-氯乙氧基乙醇分别与2-巯基芳香杂环化合物反应制得相应的芳香杂环衍生物1a1e. 以三乙胺为缚酸剂, 其与对甲苯磺酰氯反应, 生成了活化羟基的衍生物2a2e. 在碳酸钾存在下, 对叔丁基杯[4]芳烃分别与2a2e反应生成醚键连接的杂环功能基杯[4]芳烃衍生物3a3e, 并通过1H NMR, 13C NMR, IR, MS和元素分析的确证. 同时, X射线分析确定了杯[4]芳烃3a, 3b3d的晶体结构.

关键词: 杯[4]芳烃, 2-巯基芳香杂环化合物, 合成, 晶体结构

Five 2-(2-heterocycle-2-ylthioethoxy)ethanols 1a1e were prepared by the reaction of 2-(2-chloroethoxy)ethanol and 2-mercapto-heterocycles using sodium iodide as catalyst. Consequently, the compounds 1a1e reacted with tosyl chloride to afford corresponding tosylates 2a2e. A series of p-tert-butylcalix[4]arene derivatives 3a3e which contain heterocycle functional groups tethered by ether bridges were easily synthesized by the reaction of p-tert-butylcalix[4]arene with tosylated 2a2e in the presence of potassium carbonate, respectively. All new compounds were characterized by 1H NMR, 13C NMR, IR, MS techniques and elemental analysis. Meanwhile, the structures of calix[4]arene derivatives 3a, 3b and 3d were identified by X-ray diffraction analysis.

Key words: calix[4]arene, 2-mercapto-heteroaromatic compound, synthesis, crystal structure