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CN101525312A 一种3-氮杂-4-氧代-三环[4.2.1.0(2,5)]壬-7-烯的合成方法 失效 - 权利终止

一种3-氮杂-4-氧代-三环[4.2.1.0(2,5)]壬-7-烯的合成方法
摘要：
一种3－氮杂－4－氧代－三环[4.2.1.0(2，5)]壬－7－烯的合成方法，涉及一种合成具有抗肿瘤活性分子3－氨基羰基双环庚烯嘧啶二胺化合物的重要中间体的工艺。先量取2，5－降冰片二烯∶氯磺酸异氰酸酯∶弱酸盐＝1∶1－2∶1－5(摩尔比)，将2，5－降冰片二烯溶于有机溶剂中，－10－25℃滴加氯磺酸异氰酸酯，反应0.5－10小时后加入同体积的水，以及弱酸盐，0－50℃反应5－48小时，抽滤、分液、干燥、减压旋蒸去除溶剂，得到白色固体，用石油醚∶乙酸乙酯＝1∶5－1∶2重结晶，得到纯产品3－氮杂－4－氧代－三环[4.2.1.0(2，5)]壬－7－烯。本发明操作简便，产品产率达到 77％－91％，比现有方法提高15－30个百分点，纯度达到 98％以上，可广泛用于在天然产物合成。
摘要（英）：

A synthesis method of 3-aza-4-oxo-tricyclo[4.2.1.0(2,5)]non-7-ene relates to a synthesis process of an important intermediate of 3-aminocarbonylbicycloheptenylpyridinediamine compound with anti-tumor active molecules. The method comprises the following steps: measuring off 2,5-norbornadiene, chlorosulfonyl isocyanate and weak-acid salt at a ratio of 1:1-2:1-5 (mol ratio); dissolving the 2,5-norbornadiene in an organic solvent, and adding the chlorosulfonyl isocyanate dropwise at the temperature of -10-25 DEG C; allowing reacting for 0.5-10h and then adding water of the same volume and the weak-acid salt; allowing reacting at the temperature of 0-50 DEG C for 5-48h; filtrating, separating, drying and eliminating the solvent by depressurized rotary evaporation to obtain a white solid; and recrystallizing with petroleum ether and ethyl acetate at a ratio of 1:5-1:2 to obtain the net product 3-aza-4-oxo-tricyclo[4.2.1.0(2,5)]non-7-ene. The synthesis method has simple operation, high product yield up to 77-91% which is 15-30% higher than that of the existing method and purity above 98%, and can be widely used for synthesizing natural products.

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