3-amino-5-methyl-2-phenyl-2H-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: 3-amino-5-methyl-2-phenyl-2H-indazole
• 英文别名: 5-methyl-2-phenyl-2H-indazol-3-amine；5-Methyl-2-phenylindazol-3-amine
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: FNXUJVLUWOYCBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-iodo-4-methylphenyl)phenyldiazene 在 三氟化硼乙醚 作用下， 以 丙醇 、 二氯甲烷 为溶剂， 生成 3-amino-5-methyl-2-phenyl-2H-indazole
  参考文献：
  名称：

  Synthesis of 2H-Indazoles via Lewis Acid Promoted Cyclization of 2-(Phenylazo)benzonitriles

  摘要：

  Lewis-acid promoted "coarctate" cyclization of 10 2-(phenylazo) benzonitrile derivatives furnishes the isoindazole ring system in ca. 65-95% yield. A plausible mechanism for this unusual transformation is proposed.

  DOI：

  10.1021/jo060965m

文献信息

• A Palladium-Catalyzed Domino Reaction To Access 3-Amino-2<i>H</i>-indazoles from Hydrazines and 2-Halobenzonitriles
  作者：Rana Alsalim、Peter Lindemann、María Pascual López-Alberca、Sandra Miksche、Werngard Czechtizky、Nis Halland、Marc Nazaré

  DOI：10.1021/acs.orglett.0c02766

  日期：2020.9.18

  2-halobenzonitriles is presented. The reaction proceeds through a domino reaction sequence, consisting of a regioselective palladium-catalyzed coupling of monosubstituted hydrazines with 2-halobenzonitriles, followed by an intramolecular hydroamination through a 5-exo-dig cyclization and subsequent isomerization to directly afford a wide variety of substituted 2H-indazole analogues in good to excellent yields

  提出了从容易获得的2-卤代苄腈中选择性合成3-氨基-2 H-吲唑的新方法。该反应通过多米诺反应顺序进行，该顺序由单取代的肼与2-卤代苄腈的区域选择性钯催化偶联，然后通过5-exo-dig环化和随后的异构化进行分子内加氢胺化，直接得到各种取代的2 H-吲唑类似物以良好或优异的产率。
• Synthesis of 2<i>H</i>-Indazoles via Lewis Acid Promoted Cyclization of 2-(Phenylazo)benzonitriles
  作者：Laura D. Shirtcliff、Jazmin Rivers、Michael M. Haley

  DOI：10.1021/jo060965m

  日期：2006.8.1

  Lewis-acid promoted "coarctate" cyclization of 10 2-(phenylazo) benzonitrile derivatives furnishes the isoindazole ring system in ca. 65-95% yield. A plausible mechanism for this unusual transformation is proposed.