Aniline, N-(4-nitrobenzylidene)-4-phenylazo- | 80039-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: Aniline, N-(4-nitrobenzylidene)-4-phenylazo-
• 英文别名: 1-(4-nitrophenyl)-N-(4-phenyldiazenylphenyl)methanimine
• CAS: 80039-92-5
• 化学式: C₁₉H₁₄N₄O₂
• 分子量: 330.346
• InChiKey: XVZBPJGSCADVSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二氯苯氧乙酸 、 Aniline, N-(4-nitrobenzylidene)-4-phenylazo- 在 (methoxymethylidene)dimethylammonium methyl sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到3-(2,4-dichlorophenoxy)-4-(4-nitrophenyl)-1-(4-(phenyl-diazenyl)-phenyl)-azetidin-2-one
  参考文献：
  名称：

  Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt

  摘要：

  A cheap, versatile and convenient method for synthesis of beta-lactams using methoxymethylene-N,N-dimethyliminium salt as an acid activator in Staudinger reaction is reported. This method is used for the preparation of monocyclic, spirocyclic, N-alkyl and three-electron-withdrawing group beta-lactams. The products are obtained in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.009

文献信息

• A Mild and Efficient Route to 2-Azetidinones Using the Cyanuric Chloride-DMF Complex
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1055/s-0030-1289517

  日期：2011.10

  Efficient conversion of Schiff bases and carboxylic acids to β-lactams can be carried out at room temperature in CH2Cl2, using a cyanuric chloride-N,N-dimethyl formamide complex. The complex is easily prepared by reaction of cyanuric chloride and DMF, an inexpensive reagent, at room temperature. Optimization of conditions and comparison of yield with cyanuric chloride were performed.

  在室温下，利用氰尿酰氯-N,N-二甲基甲酰胺复合物，可以在CH2Cl2中高效地将席夫碱和羧酸转化为β-内酰胺。通过在室温下将氰尿酰氯与低成本试剂DMF反应，可以轻松制备该复合物。优化了条件并比较了产率与氰尿酰氯的结果。
• Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt
  作者：Aliasghar Jarrahpour、Maaroof Zarei

  DOI：10.1016/j.tet.2010.05.009

  日期：2010.7

  A cheap, versatile and convenient method for synthesis of beta-lactams using methoxymethylene-N,N-dimethyliminium salt as an acid activator in Staudinger reaction is reported. This method is used for the preparation of monocyclic, spirocyclic, N-alkyl and three-electron-withdrawing group beta-lactams. The products are obtained in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.