trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile | 49678-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile
• CAS: 49678-90-2
• 化学式: C₁₇H₁₁N₃O₂
• 分子量: 289.293
• InChiKey: BSDRPRATYNELPS-YCQNMSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile 以 苯 为溶剂， 反应 3.0h， 以82%的产率得到exo,exo-4,6-dioxo-3,5-diphenyl-2-phthalimidooctahydropyrrolo[3,4-c]pyrrole-1,3-dicarbonitrile
  参考文献：
  名称：

  Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles

  摘要：

  Thermolysis of trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile and trans-1-phthalimidoaziridine-2,3-dicarbonitrile in the presence of several dipolarophiles involves 1,3-dipolar cycloaddition to intermediate azomethine ylides and leads to 1-phthalimidopyrrolidine derivatives with good yields and high stereoselectivity. Thermally induced opening of the three-membered ring in trans-2,3-disubstituted 1-phthalimidoaziridines occurs in conrotatory mode to produce the corresponding cis-azomethine ylides in keeping with the orbital symmetry conservation rules. The relative configuration of substituents in the dipolarophiles is retained, which implies concerted mechanism of the addition.

  DOI：

  10.1134/s1070428008120105
• 作为产物：
  描述：

  肉桂腈 、 氨基邻苯二甲胺 在 lead(IV) tetraacetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile
  参考文献：
  名称：

  Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles

  摘要：

  Thermolysis of trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile and trans-1-phthalimidoaziridine-2,3-dicarbonitrile in the presence of several dipolarophiles involves 1,3-dipolar cycloaddition to intermediate azomethine ylides and leads to 1-phthalimidopyrrolidine derivatives with good yields and high stereoselectivity. Thermally induced opening of the three-membered ring in trans-2,3-disubstituted 1-phthalimidoaziridines occurs in conrotatory mode to produce the corresponding cis-azomethine ylides in keeping with the orbital symmetry conservation rules. The relative configuration of substituents in the dipolarophiles is retained, which implies concerted mechanism of the addition.

  DOI：

  10.1134/s1070428008120105

文献信息

• Intramolecular thermal transformations of N-phthalimidoaziridines: 1,3-dipolar cyclo-addition and rearrangements*
  作者：M. A. Kuznetsov、A. S. Pan’kova、V. V. Voronin、N. A. Vlasenko

  DOI：10.1007/s10593-012-0921-6

  日期：2012.2

  The intramolecular thermal cycloaddition of N-phthalimidoaziridines at multiple bonds of substituents with the intermediate formation of azomethine ylides leads to condensed pyrrole derivatives, in which the five-membered ring is adjacent to a five-, six-, or seven-membered ring. Rearrangements, which sometimes become the predominant reactions, compete with cycloaddition. Thus, aziridines with aryl

  N的分子内热环加成取代基的多个键处的邻苯二甲亚氨基氮丙啶与中间形成的甲亚胺基团导致稠合的吡咯衍生物，其中五元环与五元，六元或七元环相邻。有时成为主要反应的重排与环加成竞争。因此，具有芳基取代基的氮丙啶易于异构化，以得到邻苯二甲酰亚胺基团被1，2-转移到一个碳原子上的亚胺。具有一个吸电子取代基的氮丙啶可能不会打开以产生1,3-偶极子，而是会发生Cope型重排，涉及第二个取代基的三元环和C = O键。即使在分子内反应中，也发现氰基三键和芳环键作为双极性亲和剂的活性非常低。
• On the structure of reaction products of 2,3-disubstituted N-phthalimidoaziridines with dimethyl acetylenedicarboxylate
  作者：A. S. Pan’kova、A. V. Ushkov、M. A. Kuznetsov、S. I. Selivanov

  DOI：10.1134/s107036320904029x

  日期：2009.4