6-nitro-1-phenyl-4-phenylthio-1H-indazole | 830320-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-nitro-1-phenyl-4-phenylthio-1H-indazole
• 英文别名: 1H-Indazole, 6-nitro-1-phenyl-4-(phenylthio)-；6-nitro-1-phenyl-4-phenylsulfanylindazole
• CAS: 830320-62-2
• 化学式: C₁₉H₁₃N₃O₂S
• 分子量: 347.397
• InChiKey: XXGSWZJODAGBQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-nitro-1-phenyl-4-phenylthio-1H-indazole 在 双氧水 、 三氟乙酸 作用下， 反应 1.0h， 以96%的产率得到6-nitro-1-phenyl-4-(phenylsulfonyl)-1H-indazole
  参考文献：
  名称：

  Synthesis of polycyclic fused heterocycles based on 4,6-dinitro-1-phenyl-1H-indazole

  摘要：

  以 4-R-6- 硝基-1-苯基吲唑（R = NO2 或 SO2Ph）在第 6 和第 7 位官能化而制备的取代氨基吲唑为基础，合成了含有环状吲唑片段的呋喃三唑、沧三唑、咪唑和吡嗪系列三环杂芳香族系统。

  DOI：

  10.1007/s11172-010-0025-3
• 作为产物：
  描述：

  2,4,6-三硝基甲苯 在 吡啶 、 盐酸 、 sodium hydroxide 、 碘 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 水 为溶剂， 反应 56.0h， 生成 6-nitro-1-phenyl-4-phenylthio-1H-indazole
  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

• Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole
  作者：A. M. Starosotnikov、A. V. Lobach、V. V. Kachala、S. A. Shevelev

  DOI：10.1023/b:rucb.0000035642.41056.81

  日期：2004.3

  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.
• Synthesis of polycyclic fused heterocycles based on 4,6-dinitro-1-phenyl-1H-indazole
  作者：M. A. Bastrakov、A. M. Starosotnikov、V. V. Kachala、I. V. Glukhov、S. A. Shevelev

  DOI：10.1007/s11172-010-0025-3

  日期：2009.2

  Tricyclic heteroaromatic systems of the furoxan, vic-triazole, imidazole, and pyrazine series containing the annulated indazole fragment were synthesized based on substituted aminoindazoles prepared by the functionalization of 4-R-6-nitro-1-phenylindazoles (R = NO2 or SO2Ph) at positions 6 and 7.

  以 4-R-6- 硝基-1-苯基吲唑（R = NO2 或 SO2Ph）在第 6 和第 7 位官能化而制备的取代氨基吲唑为基础，合成了含有环状吲唑片段的呋喃三唑、沧三唑、咪唑和吡嗪系列三环杂芳香族系统。