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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

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被引次数

4

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1a～1e. 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2a～2e. 在碳酸钾存在下, 对叔丁基杯[4]芳烃分别与2a～2e反应生成醚键连接的杂环功能基杯[4]芳烃衍生物3a～3e, 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, 3b和3d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 1a～1e were prepared by the reaction of 2-(2-chloroethoxy)ethanol and 2-mercapto-heterocycles using sodium iodide as catalyst. Consequently, the compounds 1a～1e reacted with tosyl chloride to afford corresponding tosylates 2a～2e. A series of p-tert-butylcalix[4]arene derivatives 3a～3e which contain heterocycle functional groups tethered by ether bridges were easily synthesized by the reaction of p-tert-butylcalix[4]arene with tosylated 2a～2e 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