4-cyclohexylthio-3-formyl-6-nitro-1-phenyl-1H-indazole | 544676-58-6

• 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-cyclohexylthio-3-formyl-6-nitro-1-phenyl-1H-indazole
• 英文别名: 4-cyclohexylsulfanyl-6-nitro-1-phenylindazole-3-carbaldehyde
• CAS: 544676-58-6
• 化学式: C₂₀H₁₉N₃O₃S
• 分子量: 381.455
• InChiKey: ZVHRLRFSBIMRAT-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C(Solv: ethanol (64-17-5))
• 沸点：
  525.2±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.03
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酰丙酮 、 4-cyclohexylthio-3-formyl-6-nitro-1-phenyl-1H-indazole 在 氨 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以72%的产率得到3-(4-(cyclohexylthio)-6-nitro-1-phenyl-1H-indazol-3-yl)methylene-2,4-pentanedione
  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 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 32.0h， 生成 4-cyclohexylthio-3-formyl-6-nitro-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

文献信息

• Synthesis and reactions of 1-aryl-3-formyl-4,6-dinitro-1H-indazoles
  作者：Vasilii M. Vinogradov、Aleksei M. Starosotnikov、Svyatoslav A. Shevelev

  DOI：10.1070/mc2002v012n05abeh001641

  日期：2002.1

  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.