methyl 3-phenyl-1H-indazole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-phenyl-1H-indazole-1-carboxylate
• 英文别名: 3-phenyl-indazole-1-carboxylic acid methyl ester；3-Phenyl-indazol-1-carbonsaeure-methylester；Methyl 3-phenylindazole-1-carboxylate
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: VVUIMETUXOHOMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-phenyl-1H-indazole-1-carboxylate 生成 1-Methyl-3-phenylindazol 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  v. Auwers; Huettenes, Chemische Berichte, 1922, vol. 55, p. 1135

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-phenyl-2-(2-tosylhydrazono)acetate 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 苄基三乙基氯化铵 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到methyl 3-phenyl-1H-indazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of 3-Substituted Indazoles from Arynes and N-Tosylhydrazones

  摘要：

  Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo compounds and arynes.

  DOI：

  10.1021/ol201086g

文献信息

• Synthesis of Substituted 1<i>H</i>-Indazoles from Arynes and Hydrazones
  作者：Pan Li、Chunrui Wu、Jingjing Zhao、Donald C. Rogness、Feng Shi

  DOI：10.1021/jo202598e

  日期：2012.4.6

  The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.