N-(3,5-diphenyl-(115N)1H-pyrrol-2-yl)-3,5-diphenylpyrrol-2-(15N)imine | 1416550-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(3,5-diphenyl-(115N)1H-pyrrol-2-yl)-3,5-diphenylpyrrol-2-(15N)imine
• CAS: 1416550-09-8
• 化学式: C₃₂H₂₃N₃
• 分子量: 451.541
• InChiKey: XAYZBNQEQYNPQT-GHZUHFEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-硝基-1,3-二苯基-1-丁酮 在 溶剂黄146 、 <15N>ammonium acetate 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 26.0h， 生成 N-(3,5-diphenyl-(115N)1H-pyrrol-2-yl)-3,5-diphenylpyrrol-2-(15N)imine
  参考文献：
  名称：

  Mechanistic Insight into the Formation of Tetraarylazadipyrromethenes

  摘要：

  The tetraarylazadipyrromethene chromophore class has gained increasing attention in the past decade for a diverse set of scientific interests and applications. The most direct synthetic route available for their generation is heating of 4-nitro-1,3-diarylbutan-1-ones with an ammonium source in an alcohol solvent. Despite the practical simplicity, the reaction pathway(s) for these conversions are lengthy and unclear. To gain insight into the steps involved, N-15 labeling experiments with MS and NMR analysis were utilized for conversion of 4-nitro-1,3-diphenylbutan-1-one 1 into tetraphenylazadipyrromethene 2 with (NH4OAc)-N-15. To, permit examination, of later stages of the reaction sequence to 2, the N-15-labeled potential intermediate 3,5-diphenyl-1H-pyrrol-2-amine 10 was synthesized. A study of the dimerization pathway utilizing N-15-labeled 10 revealed an unprecedented nitrogen rearrangement in the final stages of the pathway involving a ring:opening/closing of a pyrrole ring. Utilizing N-15 labeling experiments we have shown that 2,4-diphenylpyrrole 8 can also react under the reaction conditions with 3,5-diphenyl-2H-pyrrol-2-imine 7 (from oxidation of 10) to. produce 2. Overall in the conversion of 1 into 2, two related pathways are ongoing concurrently, the first involves a dimerization of 3,5-diphenyl-2H-pyrrol-2-imine 7, and the other a reaction of 7 with 2,4-diphenylpyrrole 8.

  DOI：

  10.1021/jo301972w

文献信息

• Mechanistic Insight into the Formation of Tetraarylazadipyrromethenes
  作者：Marco Grossi、Aniello Palma、Shane O. McDonnell、Michael J. Hall、Dilip K. Rai、Jimmy Muldoon、Donal F. O’Shea

  DOI：10.1021/jo301972w

  日期：2012.10.19

  The tetraarylazadipyrromethene chromophore class has gained increasing attention in the past decade for a diverse set of scientific interests and applications. The most direct synthetic route available for their generation is heating of 4-nitro-1,3-diarylbutan-1-ones with an ammonium source in an alcohol solvent. Despite the practical simplicity, the reaction pathway(s) for these conversions are lengthy and unclear. To gain insight into the steps involved, N-15 labeling experiments with MS and NMR analysis were utilized for conversion of 4-nitro-1,3-diphenylbutan-1-one 1 into tetraphenylazadipyrromethene 2 with (NH4OAc)-N-15. To, permit examination, of later stages of the reaction sequence to 2, the N-15-labeled potential intermediate 3,5-diphenyl-1H-pyrrol-2-amine 10 was synthesized. A study of the dimerization pathway utilizing N-15-labeled 10 revealed an unprecedented nitrogen rearrangement in the final stages of the pathway involving a ring:opening/closing of a pyrrole ring. Utilizing N-15 labeling experiments we have shown that 2,4-diphenylpyrrole 8 can also react under the reaction conditions with 3,5-diphenyl-2H-pyrrol-2-imine 7 (from oxidation of 10) to. produce 2. Overall in the conversion of 1 into 2, two related pathways are ongoing concurrently, the first involves a dimerization of 3,5-diphenyl-2H-pyrrol-2-imine 7, and the other a reaction of 7 with 2,4-diphenylpyrrole 8.