2-(4-nitrophenyl)-9-(4-chlorophenyl)perhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(4-nitrophenyl)-9-(4-chlorophenyl)perhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-dione
• 英文别名: (2S,6R,7R)-7-(4-chlorophenyl)-4-(4-nitrophenyl)-1,4,8-triazatricyclo[6.3.0.02,6]undecane-3,5-dione
• 化学式: C₂₀H₁₇ClN₄O₄
• 分子量: 412.832
• InChiKey: BNSAJMZXAPGHAE-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 对二甲苯 为溶剂， 反应 2.5h， 生成 2-(4-nitrophenyl)-9-(4-chlorophenyl)perhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-dione
  参考文献：
  名称：

  摘要：

  Heating of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of N-arylmaleimides gives rise to 2,9-diarylperhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-diones. It is presumed that thermal cleavage of the C-N bond in the diaziridine fragment of the 6-aryl-1,5-diazabicyclo[3.1.0]hexanes results in formation of labile azomethinimines that react with N-arylmaleimides to afford the products of 1,3-dipolar cycloaddition. The rate of accumulation thereof depends only on the character of substituents in the aromatic ring of the 1,5-diazabicyclo[3.1.0]hexanes and is independent of maleimide. The thermal isomerization of 6-aryl-1.5-diazabicyclo[3.1.0]hexanes without 1,3-dipolarophiles yields the corresponding 2-pyrazolines.

  DOI：

  10.1023/a:1012465732305

文献信息

• Catalytic opening of the diaziridine fragment in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes
  作者：Yu. B. Koptelov

  DOI：10.1134/s1070428006100204

  日期：2006.10

  Treatment of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with Lewis acids [(BF3Et2O)-Et-. or In(OTf)(3)] promotes opening of the diaziridine ring, followed by formation of 1,3-dipolar cycloaddition products with N-arylmaleimides. The conversion of the initial diaziridine depends on the nature of the 6-aryl group. Diazabicyclohexanes with donor substituents react quantitatively to give (in the absence of dipolarophiles) the corresponding azomethine imine dimers, 1,2,4,5-tetrazine derivatives. The conversion of diazabicyclohexanes having acceptor substituents is poor; simultaneously, the fraction of the hydrolysis products increases. The stereoselectivity in the 1,3-dipolar cycloaddition, i.e. the ratio of the cis- and trans-adducts, depends on the catalyst and solvent. Azomethine imine dimers react with N-arylmaleimides in the presence of indium(111) trifluoromethanesulfonate to give the same 1,3-dipolar cycloaddition products as those obtained from parent 1,5-diazabicyclohexanes.
• ——
  作者：A. P. Molchanov、D. I. Sipkin、Yu. B. Koptelov、R. R. Kostikov

  DOI：10.1023/a:1012465732305

  日期：——

  Heating of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of N-arylmaleimides gives rise to 2,9-diarylperhydropyrazolo[1,2-a]pyrrolo[3,4-c]pyrazole-1,3-diones. It is presumed that thermal cleavage of the C-N bond in the diaziridine fragment of the 6-aryl-1,5-diazabicyclo[3.1.0]hexanes results in formation of labile azomethinimines that react with N-arylmaleimides to afford the products of 1,3-dipolar cycloaddition. The rate of accumulation thereof depends only on the character of substituents in the aromatic ring of the 1,5-diazabicyclo[3.1.0]hexanes and is independent of maleimide. The thermal isomerization of 6-aryl-1.5-diazabicyclo[3.1.0]hexanes without 1,3-dipolarophiles yields the corresponding 2-pyrazolines.