3-(1,3-dioxolan-2-yl)-4,6-dinitro-1-phenyl-1H-indazole | 681001-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1,3-dioxolan-2-yl)-4,6-dinitro-1-phenyl-1H-indazole
• 英文别名: 1h-Indazole,3-(1,3-dioxolan-2-yl)-4,6-dinitro-1-phenyl-；3-(1,3-dioxolan-2-yl)-4,6-dinitro-1-phenylindazole
• CAS: 681001-61-6
• 化学式: C₁₆H₁₂N₄O₆
• 分子量: 356.294
• InChiKey: QWGZDFOLVCUFLS-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C
• 沸点：
  503.5±50.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄硫醇 、 3-(1,3-dioxolan-2-yl)-4,6-dinitro-1-phenyl-1H-indazole 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 8.0h， 以61%的产率得到4-benzylthio-3-(1,3-dioxolan-2-yl)-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
• 作为产物：
  描述：

  (4,6-dinitro-1-phenyl-1H-indazol-3-yl)(ethoxy)methanol 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 14.0h， 生成 3-(1,3-dioxolan-2-yl)-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