波谱学杂志

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一种含末端炔喹啉酮类化合物的波谱学研究

刘海波,许明*,袁铃   

  1. 防化研究院,北京 102205
  • 收稿日期:2013-02-04 修回日期:2013-03-26 出版日期:2013-12-05 发布日期:2013-12-05
  • 作者简介:刘海波(1987-),男,山东济宁人,硕士研究生,主要从事有机合成研究.*通讯联系人:许明,电话:010-66758337, E-mail: uxwangxu@sohu.com.

Spectroscopic Characterization of a Quinolinone Compound with Terminal Ethynyl

LIU Hai-bo,XU Ming*,YUAN Ling   

  1. Research Institute of Chemical Defense, Beijing 102205, China
  • Received:2013-02-04 Revised:2013-03-26 Online:2013-12-05 Published:2013-12-05
  • About author:*Corresponding author: Xu Ming, Tel: 010-66758337, E-mail: uxwangxu@sohu.com.

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、1H NMR、13C NMR、1H-1H 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1H NMR和13C NMR谱的信号进行了归属.

关键词: 核磁共振(NMR), 结构, 2D NMR, 喹啉酮, 端炔基

Abstract:

The 1, 4-disubstituted 1, 2, 3-triazoles were synthesized by a click chemistry reaction, copper (I)-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1-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 1H-1H COSY and HMQC. The two configuration stereoisomers of 3 were determined by NOESY.

Key words: NMR, structure, 2D NMR, quinolinone, terminal ethynyl

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