一种含末端炔喹啉酮类化合物的波谱学研究  

Spectroscopic Characterization of a Quinolinone Compound with Terminal Ethynyl

作　　者：刘海波[1] 许明[1] 袁铃[1] 

机构地区：[1]防化研究院,北京102205

出　　处：《波谱学杂志》2013年第4期594-601,共8页Chinese Journal of Magnetic Resonance

摘　　要：通过Cu(I)催化有机叠氮化物和端基炔之间的1,3-偶极Huisgen环加成反应,又称"点击化学",可快速、高效合成专一的1,4-二取代-1,2,3-三唑产物.为得到含有末端炔的喹啉酮衍生物,以7,8-二氢-2,5(1H,6H)-二酮(1)为原料,通过烷基化反应将端基炔引入到化合物1中,合成了1-(2-炔丙基)-7,8-二氢喹啉-2,5(1H,6H)-二酮(3),并利用重结晶和硅胶柱分离两种化学手段,得到了该化合物的两种构型异构体.采用DEPT、1 H NMR、13 C NMR、1 H-1 H COSY、NOESY、HMQC多种NMR实验测试分析方法,对该化合物的构型异构体进行了验证和区分,并分别对其1 H NMR和13 C NMR谱的信号进行了归属.The 1,4-disubstituted 1,2,3-triazoles were synthesized by a click chemistry reaction,copper （D-catalyzed 1,3-dipolar cycloaddition of alkynes with azides,under mild conditions with very high yields and dramatic rate acceleration.In order to obtained quinolinone compounds with terminal ethynyl,1-（prop-2-yn-l-yl）-7,8-dihydroquinoline-2,5（1H,6H）-dione （3） was prepared from 7,8-dihydroquinoline-2,5（1H,6H）dione （1） by alkylation reaction.Two configuration stereoisomers of 3 were isolated by recrystallization and silica gel column separation.Complete assignment of the 1H and 13C NMR chemical shifts of the compound was obtained by 2D NMR techniques,including 1 H-1H COSY and HMQC.The two configuration stereoisomers of 3 were determined by NOESY

关 键 词：核磁共振(NMR) 结构 2D NMR 喹啉酮 端炔基 

分 类 号：O482.53[理学—固体物理]