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以对叔丁基杯[4]芳烃为原料,与1,2-二溴乙烷反应得到25,27-二(2-溴乙氧基)-26,28-二羟基-5,11,17,23-四叔丁基杯[4]芳烃,分别与苯佐卡因、三卡因、盐酸普鲁卡因在K2CO3、Na I/DMF体系中反应,以48%~63%的产率合成了3种新型含氨基苯甲酸酯结构的杯[4]芳烃衍生物——25,27-二(2-(对乙氧羰基苯基)氨基)乙氧基-26,28-二羟基-5,11,17,23-四叔丁基杯[4]芳烃、25,27-二(2-(3-乙氧羰基苯基)氨基)乙氧基-26,28-二羟基-5,11,17,23-四叔丁基杯[4]芳烃和25,27-二(2-(4-(2-(二乙基氨基))乙氧羰基苯基)氨基)乙氧基-26,28-二羟基-5,11,17,23-四叔丁基杯[4]芳烃。新化合物的结构与构象经元素分析、IR、1HNMR表征证实。研究它们对K+、Pb2+等9种金属离子的萃取性能以及对氨基酸的分子识别作用。结果表明,新型杯[4]芳烃衍生物对过渡金属离子具有良好的萃取效果,对Fe2+、Cu2+、Pb2+、Zn2+、Ag+的萃取率高达90%以上;同时与氨基酸也能发生很好的配合作用,能有效地识别氨基酸,对带芳环的氨基酸比脂肪氨基酸的识别效果更好。
Starting from p-tert-butyl calix [4] arene and reacting with 1,2-dibromoethane, 25,27-bis (2-bromoethoxy) -2,24,28-dihydroxy-5,11,17 , 23-tetra-tert-butyl calix [4] arene were respectively reacted with benzocaine, tricaine and procaine hydrochloride in K2CO3 and Na I / DMF system to synthesize 48% ~ 63% Three kinds of novel calix [4] arene derivatives, 25,27-bis (2- (p- ethoxycarbonylphenyl) amino) ethoxy-26,28-dihydroxy- Tert-butyl calix [4] arene, 25,27-bis (2- (3- ethoxycarbonylphenyl) amino) ethoxy-26,28-dihydroxy-5, Tert-butyl calix [4] arene and 25,27-bis (2- (4- (2- (diethylamino)) ethoxycarbonylphenyl) amino) ethoxy-26 , 28-dihydroxy-5,11,17,23-tetra-t-butyl calix [4] arene. The structure and conformation of the new compounds were confirmed by elemental analysis, IR and 1HNMR. Their extraction properties of nine metal ions such as K +, Pb2 + and their molecular recognition of amino acids were studied. The results showed that the new derivatives of calix [4] arene exhibited good extraction performance for transition metal ions, and the extraction rates of Fe2 +, Cu2 +, Pb2 +, Zn2 + and Ag + were as high as 90% , Can effectively identify amino acids, amino acids with aromatic ring recognition of fatty amino acids better.