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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (05): 681-684. 上一篇    下一篇

研究论文

四-(p-羟基苯基)杯[4]间苯二酚芳烃的烃基化和酰胺化反应

戈云1，吴萍2，韩军1，颜朝国*,1   

  1. (1扬州大学化学化工学院 扬州 225002)
    (2扬州职业大学 扬州 225009)
  • 收稿日期:2005-08-04 修回日期:2005-11-28 发布日期:2006-04-28
  • 通讯作者: 颜朝国

Alkylation and Amidation of Tetra(hydroxyphenyl)calix[4]resorcine

GE Yun1,WU Ping2,HAN Jun1,YAN Chao-Guo*,1   

  1. (1 College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002)
    (2 Yangzhou Polytechnic College, Yangzhou 225009)
  • Received:2005-08-04 Revised:2005-11-28 Published:2006-04-28
  • Contact: YAN Chao-Guo

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间苯二酚和对羟基苯甲醛在盐酸/乙醇中缩合生成四-(p-羟基苯基)杯[4]间苯二酚芳烃(1), 在K2CO3/丙酮体系中将1分别与溴乙酸乙酯、溴丙烯、N,N-二丙基氯乙酰胺反应可得到全氧烃基化产物2a～2c. 含有12个乙氧基羰基甲氧基支链的2a被苯乙胺、N,N-二甲基二丙胺或三乙烯四胺直接胺解生成杯[4]间苯二酚芳烃酰胺衍生物3a～3c. 2a经过碱性水解、酰氯化、胺化反应转化为含吡啶基的酰胺衍生物3d. 化合物结构都用1H NMR, IR和元素分析等方法进行了表征.

关键词: 杯芳烃, 酯, 间苯二酚杯芳烃, 烃基化反应, 酰胺

Tetra(p-hydroxyphenyl)calix[4]resorcine (1), prepared from the acidic condensation of resorcinol with p-hydroxybenzaldehyde in ethanol, was reacted with allyl bromide, ethyl α-chloroacetate or N,N-dipropylchloroacetamide in the system of K2CO3/KI/acetone to yield O-alkylation products 2a～2c. Aminolysis of 12 ethoxycarbonylmethoxy groups in 2a with excess 3-(dimethylamino)propylamine, N-benzyl-N-methylamine or triethylenetetramine to yield amide derivatives 3a～3c in high yields. The pyridine-linked amide derivative 3d was prepared successfully by indirect method from 2a in three steps. The structures of all compounds were characterized with elemental analysis, 1H NMR and IR spectra.

Key words: calix[4]resorcine, calixarene, alkylation, ester, amide