郑完俊, 陈淑凤. 沉香螺环化合物的研究:10-甲基-螺4.5-癸-6-烯-6-羧酸的合成J. 药学学报, 1990, 25(8): 584-589.
引用本文: 郑完俊, 陈淑凤. 沉香螺环化合物的研究:10-甲基-螺4.5-癸-6-烯-6-羧酸的合成J. 药学学报, 1990, 25(8): 584-589.
WJ Zheng, SF Chen. STUDIES ON THE SPIROCOMPOUNDS: SYNTHESIS OF 10-METHYL SPIRO 4.5 DEC-6-EN-6-CARBOXYLIC ACIDJ. Acta Pharmaceutica Sinica, 1990, 25(8): 584-589.
Citation: WJ Zheng, SF Chen. STUDIES ON THE SPIROCOMPOUNDS: SYNTHESIS OF 10-METHYL SPIRO 4.5 DEC-6-EN-6-CARBOXYLIC ACIDJ. Acta Pharmaceutica Sinica, 1990, 25(8): 584-589.

沉香螺环化合物的研究:10-甲基-螺4.5-癸-6-烯-6-羧酸的合成

STUDIES ON THE SPIROCOMPOUNDS: SYNTHESIS OF 10-METHYL SPIRO 4.5 DEC-6-EN-6-CARBOXYLIC ACID

  • 摘要: 3-甲基△2环已烯-1-酮(4)与1,4-二溴丁烷在氨钠,液氨中或在叔丁醇钾的苯溶液中进行螺环化反应,得到螺环化合物5a+5b以及双螺环化合物6a+6b。经定量催化氢化;羰基与三甲基硅氰加成反应;硅醚水解;脱水和腈基水解,合成了10-甲基-螺4.5-癸-6-烯-6-羧酸(11)。药理试验表明该化合物有一定的麻醉催眠作用。

     

    Abstract: 3-Methyl-cyclohexenone 4 spiroannulates with 1, 4-dibromobutane in NaNH2 / NH3 or t-BuOK)/benzene to afford not only themain monospiro compounds 5a and 51, but also the dispiro compounds 6a and6b, The title compound 11was synthesized from 5 through the following steps: Catalytic hydrogenation of the spiro olefmic compounds, addition of trimethylsilycyanide to the carbonyl group, hydrolysis of the siloxyl ether, dehydration of the cyanohydrin and hydrolysis of the cyano group.Compound 11 was found to have some anesthetic and hypnotic activity in animal tests.

     

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