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化学学报
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化学学报 ›› 1956, Vol. 22 ›› Issue (2): 138-143. 上一篇    下一篇

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丙烯腈的化學——Ⅲ.二螺(5, 1, 5, 3)-十六三酮-3, 7, 11的合成

金聲, 郉其毅   

  1. 北京大学化学系有机化學教研组
  • 投稿日期:1956-01-19 发布日期:2013-06-04

CHEMISTRY OF ACRYLONITRILE Ⅲ. SYNTHESIS OF DISPIRO (5, 1, 5, 3)-HEXADECANTRIONE-3, 7, 11

KING SHENG, HSING CHI-YI   

  1. Department of Chemistry, Peking University
  • Received:1956-01-19 Published:2013-06-04

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被引次数

1

1.2,2,6,6-四(β-羧乙基)-環己酮經酯化後所生成的酯,可以作為合成各種二螺系化合物的原枓,在發生Dieckmann閉環作用後,即生成4,8-二(β-乙氧羰基)-二螺(5,1,5,3)十六三酮-3,7,11。再經水解失羧後,即得到二螺(5,1,5,3)十六三酮-3,7,11。這樣的三個六碳環的二螺環系,以前還沒有報導過。2.二螺(5,1,5,3)十六三酮-3,7,11可以再和丙烯腈反應,生成2,2,4,4,10,10,12,12-八(β-氰基乙基)-二螺(5,1,5,3)十六三酮-3,7,11。利用這個化合物應當可以合成更複雜的螺系化合物。

1. A method of synthesis of compound of the dispirane type has been proposed. 4, 8-Di-(β-ethylcarboxyethyl)-dispiro (5, 1, 5, 3)-hexadecantrione-3, 7, 11 was obtained from the ethyl ester of 2, 2, 6, 6-tetra(β-carboxyethyl)-cyclohexanone by the Dieckmann's ring closure. The former was hydrolyzed and decatboxylated giving dispiro (5, 1, 5, 3) hexadecantrione-3, 7, 11. Dispirane of this type formed from three six-carbon rings so far has not been reported 2. Dispiro (5, 1, 5, 3) hexandecantrione-3, 7, 11 was allowed to react with acrylonitrile forming 2, 2, 4, 4, 10, 10, 12, 12-octo(β-cyanoethyl)-dispiro (5, 1, 5, 3) hexadecantrione-3, 7, 11. Synthesis of polyspiranes from the latter compound is now in progress in this laboratory.