4-(2,3-dihydroxypropylthio)-6-nitro-1-phenyl-1H-indazole-3-carboxaldehyde | 544676-46-2

• 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-(2,3-dihydroxypropylthio)-6-nitro-1-phenyl-1H-indazole-3-carboxaldehyde
• CAS: 544676-46-2
• 化学式: C₁₇H₁₅N₃O₅S
• 分子量: 373.389
• InChiKey: NNMJJNGLFKPOJG-UHFFFAOYSA-N

物化性质

• 沸点：
  589.3±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118.49
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(2,3-dihydroxypropylthio)-6-nitro-1-phenyl-1H-indazole-3-carboxaldehyde 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以53%的产率得到10-nitro-13-phenyl-3,16-dioxa-7-thia-13,14-diazatetracyclo[6.6.1.1^2,50^12,15]hexadeca-1(14),8(15),9,11-tetraene
  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 N-甲基吡咯烷酮 、 potassium carbonate 作用下， 反应 56.0h， 生成 4-(2,3-dihydroxypropylthio)-6-nitro-1-phenyl-1H-indazole-3-carboxaldehyde
  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