(1RS,5SR,6SR)-4-amino-6-benzoyl-2,2-bis(isopropylideneaminooxy)-3-azabicyclo[3.1.0]hex-3-ene-1,5-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1RS,5SR,6SR)-4-amino-6-benzoyl-2,2-bis(isopropylideneaminooxy)-3-azabicyclo[3.1.0]hex-3-ene-1,5-dicarbonitrile
• 英文别名: (1S,5R,6R)-2-amino-6-benzoyl-4,4-bis[(propan-2-ylideneamino)oxy]-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitrile
• 化学式: C₂₀H₂₀N₆O₃
• 分子量: 392.417
• InChiKey: BFPCQEWUBCLBIQ-BHIYHBOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1RS,5SR,6SR)-4-amino-6-benzoyl-2,2-bis(isopropylideneaminooxy)-3-azabicyclo[3.1.0]hex-3-ene-1,5-dicarbonitrile 在 硫酸 、 异丙醇 作用下， 以 水 为溶剂， 反应 0.08h， 以79%的产率得到(1RS,5SR,6SR)-6-benzoyl-2,4-dioxo-3-azabicyclo-[3.1.0]hexane-1,5-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
• 作为产物：
  描述：

  3-benzoylcyclopropane-1,1,2,2,-tetracarbonitrile 、 丙酮肟 以 乙腈 为溶剂， 反应 24.0h， 以62%的产率得到(1RS,5SR,6SR)-4-amino-6-benzoyl-2,2-bis(isopropylideneaminooxy)-3-azabicyclo[3.1.0]hex-3-ene-1,5-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