2-methyl-3-{(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl}-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-methyl-3-{(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl}-1H-indole
• 英文别名: 2-methyl-indole-3-carbaldehyde-(4-nitro-phenylhydrazone)；2-Methyl-indol-3-carbaldehyd-(4-nitro-phenylhydrazon)；2-methyl-1H-indole-3-carbaldehyde (4-nitrophenyl)hydrazone；N-[(E)-(2-methyl-1H-indol-3-yl)methylideneamino]-4-nitroaniline
• 化学式: C₁₆H₁₄N₄O₂
• 分子量: 294.313
• InChiKey: RBKVBYNUCKZGOJ-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  喹唑啉 、 2-methyl-3-{(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl}-1H-indole 、 三氟乙酸 以68%的产率得到4-(2-methyl-3-{(Z)-[2-(4-nitrophenyl)-2(2,2,2-trifluoroacetyl)hydrazinylidene]methyl}1H-indol-5-yl)-1,4-dihydroquinazolin-3-ium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline

  摘要：

  C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7 ' of the hydrazone molecule and has afforded the sigma-adducts. The C,C-coupling has been accompanied by a change in theE-configuration of the C=N bond of the starting hydrazones to theZ-configuration in the formed quinazoline trifluoroacetyl hydrazides.

  DOI：

  10.1134/s1070363220090030
• 作为产物：
  描述：

  2-甲基吲哚-3-甲醛 、 4-硝基苯肼 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以59%的产率得到2-methyl-3-{(E)-[2-(4-nitrophenyl)hydrazinylidene]methyl}-1H-indole
  参考文献：
  名称：

  Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline

  摘要：

  C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7 ' of the hydrazone molecule and has afforded the sigma-adducts. The C,C-coupling has been accompanied by a change in theE-configuration of the C=N bond of the starting hydrazones to theZ-configuration in the formed quinazoline trifluoroacetyl hydrazides.

  DOI：

  10.1134/s1070363220090030

文献信息

• Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline
  作者：Yu. A. Azev、O. S. Koptyaeva、O. S. Eltsov、Yu. A. Yakovleva、A. N. Tsmokalyuk、A. V. Ivoilova、E. A. Seliverstova、T. A. Pospelova、V. A. Bakulev

  DOI：10.1134/s1070363220090030

  日期：2020.9

  C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7 ' of the hydrazone molecule and has afforded the sigma-adducts. The C,C-coupling has been accompanied by a change in theE-configuration of the C=N bond of the starting hydrazones to theZ-configuration in the formed quinazoline trifluoroacetyl hydrazides.
• Quinazoline addition to indole hydrazone derivatives in TFA as a facile synthesis of trifluoroacetylhydrazide quinazoline σ-adducts
  作者：Yurii A. Azev、Olga S. Koptyaeva、Oleg S. Eltsov、Yulia A. Yakovleva、Tat’yana A. Pospelova、Vasiliy A. Bakulev

  DOI：10.1016/j.mencom.2020.03.032

  日期：2020.3

  Addition of indole 3-carbaldehyde arylhydrazones to quinazoline in trifluoroacetic acid occurs at the C-5-atom of the indole moiety affording quinazoline sigma-adducts with indole and trifluoroacetylhydrazide moieties.