4-benzylthio-3-(1,3-dioxolan-2-yl)-6-nitro-1-phenyl-1H-indazole

• 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-benzylthio-3-(1,3-dioxolan-2-yl)-6-nitro-1-phenyl-1H-indazole
• 英文别名: 4-(benzylsulfanyl)-3-(1,3-dioxolan-2-yl)-6-nitro-1-phenyl-1H-indazole；4-benzylsulfanyl-3-(1,3-dioxolan-2-yl)-6-nitro-1-phenylindazole
• 化学式: C₂₃H₁₉N₃O₄S
• mdl: MFCD03134010
• 分子量: 433.488
• InChiKey: BHTFYGXYQHHRQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4,6-dinitro-1-phenyl-1H-indazol-3-yl)(ethoxy)methanol 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 N-甲基吡咯烷酮 、 氯仿 为溶剂， 反应 22.0h， 生成 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

文献信息

• ——
  作者：A. M. Starosotnikov、V. V. Kachala、A. V. Lobach、V. M. Vinogradov、S. A. Shevelev

  DOI：10.1023/a:1026008821698

  日期：——

  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).