具有酯基和酰氨基的新型杯[4]冠醚与杯[6]冠醚的合成

Syntheses of a New Type of Calix[4]crown and Calix[6]crown Containing Ester and Amido Groups

乙醇胺与氯乙酰氯反应得到N ( 2 氯乙酸酯基乙基 ) 氯乙酰胺 ( 1) .1与杯 [4]芳烃和杯 [6]芳烃分别在K2 CO3 /苯和K2 CO3 /甲苯体系中反应 48h ,以 3 7%和 2 5 %的产率得到具有酯基和酰氨基的杯芳烃冠醚 .经核磁、质谱、元素分析等表征证实杯 [4]冠醚为 1 ,3 桥联方式 ,杯 [6]冠醚为 1 ,4 桥联方式 ,且均采取杯式构象 .

N-(2-Chloroacetoxyethyl)-chlor-oacetamide (1) was obtained by the reaction of ethanolamine with chloroacetyl chloride. Treatment of p-tert-butylcalix[4]arene or p-tert-butylcalix[6]arene with compound 1 under K2CO3/benzene and K2CO3/toluene system for 48 h gave the calix [4] crown and calix [6] crown containing ester and amido groups in 37% and 25% yields, respectively. The structures of new compounds were characterized by elemental analyses, FAB-MS and H-1 NMR spectra, which indicates that the new type of calixcrowns adopts cone conformation bridged at 1,3- and 1,4-positions, respectively.