5-Hydroxy-4,8-dimethyl-7-oxo-3-phenyl-6-aza-bicyclo[3.2.1]octane-1,2,2-tricarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 5-Hydroxy-4,8-dimethyl-7-oxo-3-phenyl-6-aza-bicyclo[3.2.1]octane-1,2,2-tricarbonitrile
• 英文别名: 5-Hydroxy-4,8-dimethyl-7-oxo-3-phenyl-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitrile
• 化学式: C₁₈H₁₆N₄O₂
• 分子量: 320.351
• InChiKey: AZXRGFZUTBOBIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-4,8-dimethyl-7-oxo-3-phenyl-6-aza-bicyclo[3.2.1]octane-1,2,2-tricarbonitrile 在 NR(C₂H₅)2 作用下， 以84%的产率得到3-Amino-5,7-dimethyl-1,6-dioxo-4-phenyl-4,5,6,7-tetrahydro-1H-isoindole-3a,7a-dicarbonitrile
  参考文献：
  名称：

  Reaction of 4-Oxocyclohexane-1,1,2,2-tetracarbonitriles and 5-Hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with Amines

  摘要：

  New methods have been developed for the synthesis of fused amino-substituted pyrrolidinones and dihydropyrrolones. 4-Oxocyclohexane-1,1,2,2-tetracarbonitriles react with ammonia, hydrazine, and hydroxylamine to give, respectively, 5-amino, 5-hydrazino-, and 5-hydroxylamino-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles, while with phenylhydrazine, semicarbazide, and thiosemicarbazide, 6-hydrazono-, 6-semicarbazono-, and 6-thiosemicarbazono-3-amino-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles are formed. The latter can also be obtained under analogous conditions from 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles. Reactions of 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with diethylamine or triethylamine give 3-amino-1,6-dioxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles.

  DOI：

  10.1023/b:rugc.0000039089.61023.d0

文献信息

• Reaction of 4-Oxocyclohexane-1,1,2,2-tetracarbonitriles and 5-Hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with Amines
  作者：V. P. Sheverdov、O. V. Ershov、R. N. Efimov、O. E. Nasakin、S. I. Firgang、V. A. Tafeenko

  DOI：10.1023/b:rugc.0000039089.61023.d0

  日期：2004.5

  New methods have been developed for the synthesis of fused amino-substituted pyrrolidinones and dihydropyrrolones. 4-Oxocyclohexane-1,1,2,2-tetracarbonitriles react with ammonia, hydrazine, and hydroxylamine to give, respectively, 5-amino, 5-hydrazino-, and 5-hydroxylamino-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles, while with phenylhydrazine, semicarbazide, and thiosemicarbazide, 6-hydrazono-, 6-semicarbazono-, and 6-thiosemicarbazono-3-amino-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles are formed. The latter can also be obtained under analogous conditions from 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles. Reactions of 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with diethylamine or triethylamine give 3-amino-1,6-dioxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles.