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 transisomer 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
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Key words
centchroman /
technical improvement
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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
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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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脚注
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