3-formyl-4,6-dinitro-1-phenyl-1H-indazole | 544676-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-formyl-4,6-dinitro-1-phenyl-1H-indazole
• 英文别名: 1H-Indazole-3-carboxaldehyde, 4,6-dinitro-1-phenyl-；4,6-dinitro-1-phenylindazole-3-carbaldehyde
• CAS: 544676-41-7
• 化学式: C₁₄H₈N₄O₅
• 分子量: 312.241
• InChiKey: ZJJNJHADDQUCLF-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C(Solv: ethanol (64-17-5))
• 沸点：
  466.3±45.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-formyl-4,6-dinitro-1-phenyl-1H-indazole 在 盐酸羟胺 、 乙酸酐 、 溶剂黄146 作用下， 反应 12.0h， 生成 3-cyano-4,6-dinitro-1-phenyl-1H-indazole
  参考文献：
  名称：

  摘要：

  A method for the synthesis of 1-aryl-3-formyl-4,6-dinitro-1H-indazoles by the reaction of picrylacetaldehyde with aryldiazonium salts followed by intramolecular cyclization of the resulting picrylglyoxal monoarylhydrazones was developed. Various 4,6-dinitro-1-phenyl-1H-indazoles substituted in position 3 were prepared via transformations involving the formyl group of 3-formyl-4,6-dinitro-1-phenyl-1H-indazole. 3-R-4,6-Dinitro-1-phenyl-1H-indazoles (R = CHO, CN, 1,3-dioxolan-2-yl) react regiospecifically with anionic O-, S-, and N-nucleophiles, in particular, with replacement of only the 4-NO2 group. Thus previously unknown 3-R-4-Nu-6-nitro-1-phenyl-1H-indazoles were synthesized (Nu is a nucleophile residue).

  DOI：

  10.1023/a:1026008821698
• 作为产物：
  描述：

  (4,6-dinitro-1-phenyl-1H-indazol-3-yl)(ethoxy)methanol 反应 8.0h， 生成 3-formyl-4,6-dinitro-1-phenyl-1H-indazole
  参考文献：
  名称：

  Synthesis and reactions of 1-aryl-3-formyl-4,6-dinitro-1H-indazoles

  摘要：

  The title compounds were prepared by the reactions of picrylacetaldehyde with aryldiazonium salts followed by the intramolecular cyclization of the resulting picrylglyoxal monoarylhydrazones, and the regiospecific substitution for the nitro group at the 4-position under the action of anionic N-, O- and S-nucleophiles was found.

  DOI：

  10.1070/mc2002v012n05abeh001641

文献信息

• Synthesis of 14π-electron peri-annelated tricyclic heteroaromatic systems based on 2,4,6-trinitrotoluene
  作者：Aleksei M. Starosotnikov、Vasilii M. Vinogradov、Svyatoslav A. Shevelev

  DOI：10.1070/mc2002v012n05abeh001642

  日期：2002.1

  Methyl 1-aryl-7-nitro-1H-thiopyrano[4,3,2-cd]indazol-4-carboxylates 2 and 1,5-diaryl-7-nitro-1,5-dihydropyrazolo[3,4,5-de]-cinnolines 4 were prepared based on 1-aryl-3-formyl-4,6-dinitro-1H-indazoles 1, which were synthesised previously starting from 2,4,6-trinitrotoluene.
• ——
  作者：A. M. Starosotnikov、A. V. Lobach、V. M. Vinogradov、S. A. Shevelev

  DOI：10.1023/a:1026056704860

  日期：——

  A method for the synthesis of peri-annelated trinuclear heterocycles, including 14pi-electron heteroaromatic systems, namely, 1H-thiopyrano[4,3,2-cd]indazoles and 1,5-dihydropyrazolo[3,4,5-de]cinnolines, from 3-R-1-aryl-4,6-dinitro-1H-indazoles was developed. The method is based on the high mobility of the NO2 group in position 4 and consists of either selective nucleophilic substitution of the 4-NO2 group on treatment with the HSCH2CO2Me-K2CO3 system followed by intramolecular cyclization of the resulting sulfide (R = CHO) or the corresponding sulfone (R = CN) formed upon its oxidation or direct intramolecular substitution of the 4-NO2 group (R = CH=NNH Ph).