1-phenyl-2-(2,4,6-trinitrobenzylidene)hydrazine | 830320-61-1

• 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: 1-phenyl-2-(2,4,6-trinitrobenzylidene)hydrazine
• 英文别名: 2,4,6-trinitrobenzaldehyde N-phenylhydrazone；N-[(2,4,6-trinitrophenyl)methylideneamino]aniline
• CAS: 830320-61-1
• 化学式: C₁₃H₉N₅O₆
• 分子量: 331.244
• InChiKey: JJTXRRYBZCBSIU-UHFFFAOYSA-N

物化性质

• 沸点：
  503.0±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  153.81
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(2,4,6-trinitrobenzylidene)hydrazine 在 sodium hydroxide 、 三氯化铁 、 甲烷 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 6-硝基-1-苯基吲唑-4-胺
  参考文献：
  名称：

  Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole

  摘要：

  The reactions of 4,6-dinitro-1-phenyl-1H-indazole with anionic nucleophiles RS- and N-3(-) lead to the regiospecific replacement of the nitro group at position 4. The reaction with N2H4 . H2O + FeCl3 also results in reduction of only the 4-NO2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1H-indazoles (X is a residue of a nucleophile or NH2). Comparison of the data on the selective nucleophilic substitution (4-NO2 group) in 3-Z-1-aryl-4,6-dinitro-1H-indazoles shows that in the case of Z = H, the regiospecificity of substitution is determined by the electronic effect of the annelated pyrazole ring.

  DOI：

  10.1023/b:rucb.0000035642.41056.81
• 作为产物：
  描述：

  2,4,6-三硝基甲苯 在 吡啶 、 盐酸 、 碘 作用下， 以 乙醇 为溶剂， 反应 50.0h， 生成 1-phenyl-2-(2,4,6-trinitrobenzylidene)hydrazine
  参考文献：
  名称：

  Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole

  摘要：

  The reactions of 4,6-dinitro-1-phenyl-1H-indazole with anionic nucleophiles RS- and N-3(-) lead to the regiospecific replacement of the nitro group at position 4. The reaction with N2H4 . H2O + FeCl3 also results in reduction of only the 4-NO2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1H-indazoles (X is a residue of a nucleophile or NH2). Comparison of the data on the selective nucleophilic substitution (4-NO2 group) in 3-Z-1-aryl-4,6-dinitro-1H-indazoles shows that in the case of Z = H, the regiospecificity of substitution is determined by the electronic effect of the annelated pyrazole ring.

  DOI：

  10.1023/b:rucb.0000035642.41056.81

文献信息

• Potassium tert-Butoxide Promoted Intramolecular Amination of 1-Aryl-2- (2-nitrobenzylidene)hydrazines: Efficient Synthesis of 1-Aryl-1H-indazoles
  作者：Abbas Shafiee、Fatemeh Esmaeili-Marandi、Mina Saeedi、Mohammad Mahdavi、Issa Yavari、Alireza Foroumadi

  DOI：10.1055/s-0034-1379084

  日期：——

  1-Aryl-2-(2-nitrobenzylidene)hydrazines readily undergo intramolecular amination to afford 1-aryl-1H-indazole derivatives. The reaction was conducted in the presence of potassium tert-butoxide in N,N-dimethylformamide (DMF) at 100 °C and all products were obtained in good yields. Displacement of the nitro group was achieved in the absence of significant electron-withdrawing substituents such as nitro

  1-Aryl-2-(2-nitrobenzylidene)hydrazines 很容易进行分子内胺化，得到 1-aryl-1H-indazole 衍生物。该反应在叔丁醇钾的存在下在 N,N-二甲基甲酰胺 (DMF) 中于 100 °C 下进行，所有产物均以良好的收率获得。在没有显着的吸电子取代基如硝基、氰化物、重氮或羰基的情况下实现了硝基的置换。