N-Phenylimide of cis-1,2-cyclopropanedicarboxylic acid | 3120-05-6

• 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: N-Phenylimide of cis-1,2-cyclopropanedicarboxylic acid
• 英文别名: 3-phenyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione；3-Phenyl-3-aza-bicyclo[3.1.0]hexan-2,4-dion；Cyclopropan-2,3-(N-phenyl)-dicarboximid；3-Phenyl-3-azabicyclo[3.1.0]hexane-2,4-dione
• CAS: 3120-05-6
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: MOLSZXACYHAGBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  423.5±14.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Phenylimide of cis-1,2-cyclopropanedicarboxylic acid 在 盐酸 作用下， 生成 cis-1,2-cyclopropanedicarboxylic acid
  参考文献：
  名称：

  Majchrzak, Michael W.; Kotelko, Antoni, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1475 - 1477

  摘要：

  DOI：
• 作为产物：
  描述：

  7-Phenyl-2,3,7-triazabicyclo<3.3.0>oct-2-ene-6,8-dione 生成 N-Phenylimide of cis-1,2-cyclopropanedicarboxylic acid
  参考文献：
  名称：

  MAJCHRZAK, M. W., ACTA POL. PHARM., 1982, 39, N 4, 289-294

  摘要：

  DOI：

文献信息

• Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes
  作者：Saori Shiraki、Cortnie S. Vogelsberg、Miguel A. Garcia-Garibay

  DOI：10.1039/c2pp25263e

  日期：2012.12

  To expand on the limited number of examples that exist in the literature for the solid-state photodenitrogenation of azoalkanes, a series of crystalline 7-alkyl-2,3,7-triazabicyclo[3.3.0]oct-2-ene-6,8-diones with varying 4,4-substituents were prepared. Their photochemical behavior in solution and in the solid state was dependent on the 4,4-substitution of the 1-pyrazoline ring, with unsubstituted pyrazoline 12 giving a mixture of products both in solution and in the solid state. Diphenyl substituted pyrazolines 13 denitrogenate spontaneously in solution but require light exposure to react quantitatively in the solid state. t-Butyl-phenyl substituted pyrazolines 14 were shown to denitrogenate both chemo- and diastereoselectively in solution and in the solid state to yield a single product in quantitative yield.

  为了扩展文献中关于偶氮烷烃固态光脱氮反应的有限实例，我们制备了一系列具有不同4,4-取代基的7-烷基-2,3,7-三氮杂双环[3.3.0]辛-2-烯-6,8-二酮晶体。它们在溶液和固态下的光化学行为取决于1-吡唑啉环的4,4-取代基，未取代的吡唑啉12在溶液和固态下都会产生混合产物。二苯基取代吡唑啉13在溶液中自发脱氮，但在固态下需要光照才能定量反应。叔丁基苯基取代吡唑啉14在溶液和固态下均表现出化学和立体选择性脱氮，以定量产率产生单一产物。
• Gregory; Perkin, Journal of the Chemical Society, 1903, vol. 83, p. 784
  作者：Gregory、Perkin

  DOI：——

  日期：——
• Reactions with Diazoalkanes. V. Action of Diazoalkanes and of Aryl Azides on N-Arylmaleimides
  作者：Ahmed Mustafa、Salah Mohamed Abdel Dayem Zayed、Samir Khattab

  DOI：10.1021/ja01582a041

  日期：1956.1
• Notes-Reactions with Diazoalkanes. I. Action of Diazomethane on N-Phenylmaleimide, with a Special Note on the Pyrolysis Products of the Pyrazoline
  作者：William Awad、Sayed Abdel、Rahman Omran、Michael Sobhy

  DOI：10.1021/jo01068a613

  日期：1961.10
• MAJCHRZAK, M. W.;KOTELKO, A., J. HETEROCYCL. CHEM., 1985, 22, N 6, 1475-1477
  作者：MAJCHRZAK, M. W.、KOTELKO, A.

  DOI：——

  日期：——