西替考马合成路线的优化

季小慎;金涛;刘延苗;奕宋鹏

中国药学杂志 ›› 1998, Vol. 33 ›› Issue (02) : 109-110.

中国药学杂志 ›› 1998, Vol. 33 ›› Issue (02) : 109-110.
药物化学

西替考马合成路线的优化

  • 季小慎; 金涛; 刘延苗; 奕宋鹏
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The improvement for synthesis of centchroman

  • Ji Xiaoshen
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摘要

目的:优化西替考马的合成路线、简化操作方法和提高反应产率。方法:通过改变反应起始物,重新设计反应路线。特别是利用2,2二甲基-3-苯基-7-甲氧基苯并吡喃(2)中的双键和苯酚进行Friedel-Crafts烷基化反应。结果:以五步反应获到最终产物。其中在Friedel-Crafts烷基化反应中高选择性的获得反式异构体,总收率达40%。结论:避免了文献报道中的高压氢化和构型转化两个反应单元,简化了合成路线并提高了反应产率。

Abstract

OBJECTIVE: To improve the synthesis and promote the yield for centchroman. METHODS: The reported synthetic route was simplified and redesigned, especially using 2, 2-dimethyl-3-phenyl-7-methoxychromene (2) to react with phenol. RESULTS: The transisomer was got in the step of highly stereo-selective Friedel-Crafts alkylation and final product centchroman was got just by five steps with over all yield of 40%. CONCLUSION: The synthesis for centchroman was simplified and yield was increased with out two steps of hydrogenation in high pressure and configuration transformation which appeared in the reported route.

关键词

西替考马 / 技术优化

Key words

centchroman / technical improvement

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导出引用
季小慎;金涛;刘延苗;奕宋鹏. 西替考马合成路线的优化[J]. 中国药学杂志, 1998, 33(02): 109-110
Ji Xioshen . The improvement for synthesis of centchroman [J]. Chinese Pharmaceutical Journal, 1998, 33(02): 109-110

参考文献

1 Lyer SS.India launches the new weekly contraceptive pill.Drug News Perspect,1991,4(4):228. 2 Ray S,Grover PK,Anand N.A new synthesis of cis-& trans-3-phenyl-4-[4-(β-pyrrolidinoethoxy)-phenyl]-7-methoxy-chromans.Indian J Chem,1971,9(7):727. 3 Jamas W B.Process for preparation of substituted 3,4-(diphenyl) chromans.US Pat,3,822,287.1974-07-02. 4 季小慎,严久凤,王雪峰.7-甲氧基-3-苯基香豆素的合成中国医药工业杂志,1996,27(3):133.

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