(E)-1-(2,2-dimethylhexa-3,4-dienylidene)-2-(2,4-dinitrophenyl)hydrazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-(2,2-dimethylhexa-3,4-dienylidene)-2-(2,4-dinitrophenyl)hydrazine
• 英文别名: (1E)-2,2-dimethylhexa-3,4-dienal (2,4-dinitrophenyl)hydrazone
• 化学式: C₁₄H₁₆N₄O₄
• 分子量: 304.305
• InChiKey: KILSKCLIRYCNGD-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(2,2-dimethylhexa-3,4-dienylidene)-2-(2,4-dinitrophenyl)hydrazine 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) (2:1) toluene adduct 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以93%的产率得到N-(2,4-dinitrophenyl)-5-ethyl-2,3-dimethyl-1H-pyrrol-1-amine
  参考文献：
  名称：

  Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles

  摘要：

  The gold(I)-catalyzed cycloisomerization of beta-allenylhydrazones provides an efficient access to multisubstituted N-aminopyrroles, which are obtained in good to excellent yields. This new intramolecular cyclization method can be applied either to alkyl- or aryl-substituted allenes. The reaction proceeds under mild conditions with short reaction times through a selective intramolecular 1,2-alkyl or -aryl migration extending the general scope of the reaction.

  DOI：

  10.1021/ol101889h
• 作为产物：
  描述：

  2,2-dimethylhexa-3,4-dienal 、 2,4-二硝基苯肼 在 magnesium sulfate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以60%的产率得到(E)-1-(2,2-dimethylhexa-3,4-dienylidene)-2-(2,4-dinitrophenyl)hydrazine
  参考文献：
  名称：

  Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles

  摘要：

  The gold(I)-catalyzed cycloisomerization of beta-allenylhydrazones provides an efficient access to multisubstituted N-aminopyrroles, which are obtained in good to excellent yields. This new intramolecular cyclization method can be applied either to alkyl- or aryl-substituted allenes. The reaction proceeds under mild conditions with short reaction times through a selective intramolecular 1,2-alkyl or -aryl migration extending the general scope of the reaction.

  DOI：

  10.1021/ol101889h

文献信息

• Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted <i>N</i>-Aminopyrroles
  作者：Erica Benedetti、Gilles Lemière、Laure-Lise Chapellet、Andrea Penoni、Giovanni Palmisano、Max Malacria、Jean-Philippe Goddard、Louis Fensterbank

  DOI：10.1021/ol101889h

  日期：2010.10.1

  The gold(I)-catalyzed cycloisomerization of beta-allenylhydrazones provides an efficient access to multisubstituted N-aminopyrroles, which are obtained in good to excellent yields. This new intramolecular cyclization method can be applied either to alkyl- or aryl-substituted allenes. The reaction proceeds under mild conditions with short reaction times through a selective intramolecular 1,2-alkyl or -aryl migration extending the general scope of the reaction.

表征谱图