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化学学报
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化学学报 ›› 1982, Vol. 40 ›› Issue (6): 551-556. 上一篇    下一篇

论文

8-甲氧基呋喃并[3’, 2’：6, 7]香豆素与溴反应的研究

安静仪, 张曼华, 马俊兰   

  1. 中国科学院北京感光化学研究所
  • 投稿日期:1981-02-01 发布日期:2013-06-03
  • 通讯作者: 安静仪

THE REACTION BETWEEN 8-METHOXYPSORALEN AND BROMINE

AN JING-YI, ZHANG MAN-HUA, MA JUN-LAN   

  1. Beijing Institute of Photographic Ohemistry, Aoademia Sinica
  • Received:1981-02-01 Published:2013-06-03

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在溴和8-甲氧基呋喃并[3',2':6,7]香豆素(1,8-MOP)及NBS与1的反应中发现,溴首先在C5取代,其次加到C4',5'双键上,最后加到C3,4双键上,得到新化合物3,4,5,4',5'-五溴-3,4,4',5'-四氢-8-MOP(4).比较了1和香豆素对NBS反应的活性,发现NBS对香豆素不发生加成反应.这是由于1中的甲氧基和呋哺环使其对亲电试剂的反应活性比香豆素高,并由13C核磁共振谱的C3化学位移及这两个化合物中各双键的可极化率得到证实.4与二乙胺和吡啶的消除反应分别得到新化合物5和6.

The reaction betweon bromine and 8-methogypsoralen(1) and that between NBS and 1 have been studied in detail. It was shown that at first the hydrogen at 5 position of 1 was substituted by bromine, then a molecule of bromine was added onto 4', 5' double bond and finally another moleoule of bromine was added onto 3, 4 double bond. It was clearly demonstrated that 3, 4 double bond of 1 is reactive toward bromine or NBS. This reaction has not been reported previously and the new compound, 3, 4, 5, 4', 5'-pentabromo-3, 4, 4', 5'-tetrahydro-8-methoxypsoralen (4),was obtained.