4,6-dinitro-1-phenyl-1H-indazole | 312517-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,6-dinitro-1-phenyl-1H-indazole
• 英文别名: 4,6-dinitro-1-phenylindazole
• CAS: 312517-63-8
• 化学式: C₁₃H₈N₄O₄
• mdl: MFCD01572901
• 分子量: 284.231
• InChiKey: QXXWTCAAXSJILS-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C(Solv: ethanol (64-17-5))
• 沸点：
  417.9±38.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-dinitro-1-phenyl-1H-indazole 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以83%的产率得到4-azido-6-nitro-1-phenyl-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
• 作为产物：
  描述：

  2,4,6-三硝基甲苯 在 吡啶 、 盐酸 、 sodium hydroxide 、 碘 作用下， 以 乙醇 、 水 为溶剂， 反应 51.0h， 生成 4,6-dinitro-1-phenyl-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

• Synthesis of 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to azoles
  作者：E. M. Asadulina、M. A. Bastrakov、A. M. Starosotnikov、V. V. Kachala、S. A. Shevelev

  DOI：10.1007/s11172-010-0026-2

  日期：2009.2

  3-R-1,5-Dinitro-3-azabicyclo[3.3.1]nonanes fused to the pyrazole, thiazole, and triazole rings were synthesized by reductive cyclization of meta-dinitrobenzazoles.

  3-R-1,5-二硝基-3-氮杂双环[3.3.1]壬烷与吡唑、噻唑和三唑环的融合化合物，通过间二硝基苯并异恶唑的还原环化反应合成。
• Double 1,3-dipolar cycloaddition of N-methyl Azomethine ylide to meta-Dinitrobenzene annelated with nitrogen aromatic heterocycles
  作者：Maxim A. Bastrakov、Alexey M. Starosotnikov、Sergey Yu. Pechenkin、Vadim V. Kachala、Ivan V. Glukhov、Svyatoslav A. Shevelev

  DOI：10.1002/jhet.423

  日期：——

  The 1,3-dipolar cycloaddition of unstabilized azomethine ylide 1 with meta-dinitrobenzene fused with nitrogen heterocycles affords the corresponding decahydropyrrolo[3,4-e]isoindole cycloadducts in good yields. This is a first example of [3+2]-cycloaddition of azomethine ylides to nitroarenes. J. Heterocyclic Chem., (2010).

  未稳定的甲亚胺基内酯1与间二硝基苯与氮杂环稠合的1,3-偶极环加成反应可提供相应的十氢吡咯并[3,4- e ]异吲哚环加合物，收率很高。这是将甲亚胺烷基化物[3 + 2]-环加成成硝基芳烃的第一个例子。J.杂环化​​学。（2010）。
• Synthesis of pyrazole- and thiazole-annulated 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes
  作者：A. V. Puchnin、M. A. Bastrakov、A. M. Starosotnikov、S. V. Popkov、S. A. Shevelev

  DOI：10.1007/s11172-012-0086-6

  日期：2012.3

  The previously unknown 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to the pyrazole or thiazole rings were synthesized by the reductive cyclization of m-dinitroindazoles and benzothiazoles. The method is based on the reduction of carbon-carbon bonds in the benzene ring, which are activated by the meta-nitro groups, with NaBH4 followed by the Mannich reaction with formaldehyde and primary amines.

  通过间二硝基吲唑和苯并噻唑的还原环化反应，合成了以前未知的与吡唑或噻唑环融合的 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes 。该方法的基础是用 NaBH4 还原苯环中的碳碳键（这些碳碳键由偏硝基活化），然后与甲醛和伯胺发生曼尼希反应。
• 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。
• 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。