含香豆素荧光基团的杯[4]吡咯分子合成与表征

Synthesis and Characterization of Coumarin-strapped Calix[4]pyrrole Molecules

为了开发新型含香豆素荧光基团的杯[4]吡咯分子用作阴离子识别的荧光探针,以对氨基苯乙酮、丙酮和新蒸吡咯为原料,盐酸作为催化剂,合成了meso-七甲基-meso-对氨基杯[4]吡咯化合物1.以2-羟基-1-萘甲醛,4-二乙氨基水杨醛,水杨醛,4-甲氧基水杨醛和丙二酸二乙酯为原料,以六氢吡啶和醋酸为催化剂合成香豆素酯类,并经水解反应得到了香豆素酸类化合物2～5,将1和2～5分别在DCC/DMAP的催化或利用酰氯的酰胺化反应合成了一系列含香豆素荧光基团的杯[4]吡咯分子6～9,其中1和6～9为未见文献报道的新化合物,所有合成的化合物的结构已由核磁共振氢谱(1 H NMR),质谱(MS)和元素分析等方法进行了结构表征.

In order to develope a new coumarin-strapped calix[4]pyrrole molecule fluorescent probe for anions,a series of coumarin-strapped calix[4]pyrrole compounds 6～9 was synthesized by coupling meso-heptamethyl-meso-paminophenyl cali[4]pyrrole 1 with coumarins acids 2～5 under the catalysis of DCC/DMAP or the amidation of acyl chloride.1 was synthesized by using p-aminoacetophenone,acetone and pyrrole as the starting materials and HCl as the catalyst.2～5 were synthesized through Knoevnagal reaction and hydrolysis,with2-hydroxy-1-naphthaldehyde,4（diethyl）aminosalicylaldehyde,salicylaldehyde,4-methoxy salicylaldehyde and diethyl malonate,and piperidine as the starting materials and acetic acid as the catalysts.Among the synthesized compounds,1 and 6～9 were new compounds.The structures of the synthesized compounds were characterized by 1 HNMR,MS and elemental analysis.