1-p-nitrophenylimino-2-p-methylphenylisoindoline

• 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: 1-p-nitrophenylimino-2-p-methylphenylisoindoline
• 英文别名: 2-(4-methylphenyl)-N-(4-nitrophenyl)-3H-isoindol-1-imine
• 化学式: C₂₁H₁₇N₃O₂
• 分子量: 343.385
• InChiKey: LJOVTLDYLSQVQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  palladium diacetate 、 1-p-nitrophenylimino-2-p-methylphenylisoindoline 以 二氯甲烷 为溶剂， 以36%的产率得到
  参考文献：
  名称：

  Synthesis of mixed N,N′-(Ar,Ar′-diaryl)iminoisoindolines for applications in palladacycle formations

  摘要：

  The synthesis of N,N'-(Ar,Ar'-diaryl)iminoisoindolines containing different aryl groups bound to the two nitrogen atoms is described. The iminoisoindolines were obtained by a three component, one-pot reaction of phthalaldehyde with 1 equivalent p-NO2-aniline and 1 equivalent p-R-aniline, where R = H, Me, MeO or Pr-i, resulting in formation of non-symmetrically substituted (mixed) iminoisoindolines, 1-p-nitrophenylimino-2-p-R-phenylisoindoline (R = H (1), Me (2), MeO (3), and Pr-i (4)), as analytically pure precipitates requiring no further purification. Only one isomer precipitates from solution wherein the nitro group resides exclusively at the imine position while the more electron donating substituent ends up on the isoindoline ring position. Further reaction with Pd(OAc)(2) in dichloromethane at room temperature results in formation of six-membered [C,N] dinuclear cyclopalladated complexes with the general formula [(Ar,Ar'-diaryliminoisoindoline)Pd{mu-OAc}](2). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.09.054
• 作为产物：
  描述：

  乙烷,三氯氟- 、 4-硝基苯胺 、 邻苯二甲醛 在 甲酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 以55%的产率得到1-p-nitrophenylimino-2-p-methylphenylisoindoline
  参考文献：
  名称：

  Synthesis of mixed N,N′-(Ar,Ar′-diaryl)iminoisoindolines for applications in palladacycle formations

  摘要：

  The synthesis of N,N'-(Ar,Ar'-diaryl)iminoisoindolines containing different aryl groups bound to the two nitrogen atoms is described. The iminoisoindolines were obtained by a three component, one-pot reaction of phthalaldehyde with 1 equivalent p-NO2-aniline and 1 equivalent p-R-aniline, where R = H, Me, MeO or Pr-i, resulting in formation of non-symmetrically substituted (mixed) iminoisoindolines, 1-p-nitrophenylimino-2-p-R-phenylisoindoline (R = H (1), Me (2), MeO (3), and Pr-i (4)), as analytically pure precipitates requiring no further purification. Only one isomer precipitates from solution wherein the nitro group resides exclusively at the imine position while the more electron donating substituent ends up on the isoindoline ring position. Further reaction with Pd(OAc)(2) in dichloromethane at room temperature results in formation of six-membered [C,N] dinuclear cyclopalladated complexes with the general formula [(Ar,Ar'-diaryliminoisoindoline)Pd{mu-OAc}](2). (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.09.054

文献信息

• Synthesis of mixed N,N′-(Ar,Ar′-diaryl)iminoisoindolines for applications in palladacycle formations
  作者：Jackson M. Chitanda、Shih-Chang Wu、J. Wilson Quail、Stephen R. Foley

  DOI：10.1016/j.ica.2011.09.054

  日期：2011.12

  The synthesis of N,N'-(Ar,Ar'-diaryl)iminoisoindolines containing different aryl groups bound to the two nitrogen atoms is described. The iminoisoindolines were obtained by a three component, one-pot reaction of phthalaldehyde with 1 equivalent p-NO2-aniline and 1 equivalent p-R-aniline, where R = H, Me, MeO or Pr-i, resulting in formation of non-symmetrically substituted (mixed) iminoisoindolines, 1-p-nitrophenylimino-2-p-R-phenylisoindoline (R = H (1), Me (2), MeO (3), and Pr-i (4)), as analytically pure precipitates requiring no further purification. Only one isomer precipitates from solution wherein the nitro group resides exclusively at the imine position while the more electron donating substituent ends up on the isoindoline ring position. Further reaction with Pd(OAc)(2) in dichloromethane at room temperature results in formation of six-membered [C,N] dinuclear cyclopalladated complexes with the general formula [(Ar,Ar'-diaryliminoisoindoline)Pdmu-OAc}](2). (C) 2011 Elsevier B.V. All rights reserved.