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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (02): 252-258. 上一篇    下一篇

研究论文

螺[1-溴-4-甲氧基-5-氧杂-6-氧代双环[3.1.0]己烷-2,2¢-(3-{α-[二(乙氧基)膦酸酯基]苄氧基}-4-甲氧基-5-氧杂-1-氧代环戊烷)]的合成、 结构及抗肿瘤活性的研究

裴 强* ; 金春雪 ; 牛满丽; 程志红   

  1. (信阳师范学院化学化工学院 信阳 464000)
  • 收稿日期:2008-05-14 修回日期:2008-07-24 发布日期:2009-02-20
  • 通讯作者: 裴 强

Synthesis, Structure and Anti-tumor activity of Spiro[(1-bromo-4-me- thoxy-5-oxa-6-oxobicyclo[3.1.0]hexane-2,2’-(3-{α-[di(ethoxy)phos- phoryl]benzyloxy}-4-methoxy-5-oxa-1-oxocyclopentane]

Pei, Qiang*; Jin, Chunxue; Niu, Manli; Cheng, Zhihong   

  1. (Department of Chemistry, Xinyang Normal University, Xinyang 464000)

  • Received:2008-05-14 Revised:2008-07-24 Published:2009-02-20
  • Contact: Pei, Qiang

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α-羟基取代膦酸酯和5-甲氧基-3-溴-2(5H)-呋喃酮通过不对称串联反应, 得到螺环-膦酸酯类化合物的非对映异构体5和6. 目标分子5和6经IR, 1H NMR, 13C NMR, MS, 元素分析进行了结构表征, 其中非对映异构体5c和6c的立体化学结构通过X射线晶体分析得到了确认. 此研究结果为某些复杂的有机磷化合物提供了新的合成策略.

关键词: 抗肿瘤活性, 不对称串联反应, 螺环-膦酸酯类化合物, X射线晶体分析

Racemic diastereoisomeric spiro-phosphonate derivatives 5～6 were obtained by tandem double Michael addition and intramolecular nucleophilic substitution of 3-bromo-5-methoxy-5H-furan-2-one and α-hydroxylbenzylphosphonate under a warm condition. The target compounds 5～6 were identified by the elemental analysis, IR, 1H NMR, 13C NMR and MS techniques. The stereochemistry and configuration of 5c and 6c were confirmed further by X-ray crystallography. This result could lead to a new strategy for the synthesis of some complicated compounds containing a phosphorus functional group.

Key words: spiro-phosphonate derivate, X-ray crystallography, anti-tumor activity, tandem asymmetric reaction