(4RS,5SR)-8-methyl-3,6-dioxo-1-phenyl-2,7-diazatricyclo[3.2.1.0(4,8)]octane-4,5-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4RS,5SR)-8-methyl-3,6-dioxo-1-phenyl-2,7-diazatricyclo[3.2.1.0(4,8)]octane-4,5-dicarbonitrile
• 英文别名: (2S,8R)-1-methyl-3,7-dioxo-5-phenyl-4,6-diazatricyclo[3.3.0.02,8]octane-2,8-dicarbonitrile
• 化学式: C₁₅H₁₀N₄O₂
• 分子量: 278.27
• InChiKey: BPOGVPGFMYRWLV-HFDVOGEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzoyl-1-methylcyclopropane-2,2,3,3-tetracabonitrile 在 硫酸 、 水 作用下， 以71%的产率得到(4RS,5SR)-8-methyl-3,6-dioxo-1-phenyl-2,7-diazatricyclo[3.2.1.0(4,8)]octane-4,5-dicarbonitrile
  参考文献：
  名称：

  Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with water

  摘要：

  3-Benzoylcyclopropane-1,1,2,2-tetracarbonitrile reacted with water to give 2-benzoyl-1,3-dicyanocyclopropane-1-carboxamide as a result of hydrolysis of the cyano group in the trans position with respect to the carbonyl group and subsequent decarboxylation. The reaction of 3-benzoyl-3-methylcyclopropane-1,1,2,2-tetracarbonitrile with water involved heterocyclization with participation of the carbonyl group and cis-cyano groups, leading to 8-methyl-3,6-dioxo-1-phenyl-2,7-diazatricyclo[3.2.1.0(4,8)]octane-4,5-dicarbonitrile. Hydrolysis of 3-alkylcyclopropane-1,1,2,2-tetracarbonitrile followed both reaction paths to produce mixtures of products, including 7-alkyl-4-amino-7-hydroxy-1,9-dioxo-3,8-diazatricyclo[4.3.0.0(1,5)]non-3-ene-5-carbonitriles. In all cases, the three-membered ring was retained.

  DOI：

  10.1134/s1070428012040033