摘要
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。
The 25,27-（ 2-bromine ethoxy）-26,28-hydroxy-5,11,17,23-tert-butyl calix [4]arene was synthesized by using p-tertbutyl calix[4]arene and 1,2-dibromoethane. Three new calix [4]arene,such as 25,27-（ 2-（ 4-ethoxy carbonyl phenyl） amino）ethoxy-26,28-hydroxy-5,11,17,23-tert-butyl calix [4] arene,25,27-（ 2-（ 3-ethoxy carbonyl phenyl） amino） ethoxy-26,28-hydroxy-5,11,17,23-tert-butyl calix [4]arene and 25,27-（ 2-（ 4-（ 2-（ diethyl amine）） ethoxy carbonyl phenyl） amino） ethoxy-26,28-hydroxy-5,11,17,23-tert-butyl calix [4] arene,were synthesized by reacting p-tert-butyl-calix[4]arene compound 1 with benzocaine,tricaine,procaine in K2CO3,Na I/DMF system with 47% ~ 63% yields. The structures were confirmed by elemental analyses,IR,1HNMR. Their extraction properties toward K＋,Pb2 ＋and some other metal ions and recognition performance toward amino acid was evaluated. The results showed that compounds 2 ~ 4 have excellent extraction efficiency towards transition metal ions,the extracted percentage of Fe2 ＋,Cu2 ＋,Pb2 ＋,Zn2 ＋,Ag＋were as high as 90% above. Meanwhile,the products could identify well L-Tyr and its derivatives.
出处
《化学试剂》
CAS
北大核心
2015年第2期104-108,共5页
Chemical Reagents
关键词
杯[4]芳烃衍生物
合成
金属离子萃取
氨基酸识别
calix[4]arene derivative
synthesis
extraction of metal ions
recognition of amino acid
