1-phenyl-3-(o-tolyl)-1H-indazole | 1394164-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-3-(o-tolyl)-1H-indazole
• 英文别名: 3-(2-Methylphenyl)-1-phenylindazole；3-(2-methylphenyl)-1-phenylindazole
• CAS: 1394164-17-0
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: KEAFOXZUTGVOIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-1H-吲唑 、 2-碘代甲苯 在 potassium phosphate 、 1,10-菲罗啉 、 silver carbonate 、 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以65%的产率得到1-phenyl-3-(o-tolyl)-1H-indazole
  参考文献：
  名称：

  Pd- and Cu-catalyzed C–H arylation of indazoles

  摘要：

  The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl2/phen/Ag2CO3/K3PO4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.091

文献信息

• An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere
  作者：Jin Yu、Jin Woo Lim、Su Yeon Kim、Jimin Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2015.01.183

  日期：2015.3

  An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 degrees C afforded 1Hindazoles in good yields most likely via a sequential intramolecular nucleophilic cyclization and an aerobic oxidation pathway. (C) 2015 Elsevier Ltd. All rights reserved.
• Pd- and Cu-catalyzed C–H arylation of indazoles
  作者：Keika Hattori、Kazuya Yamaguchi、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1016/j.tet.2012.05.091

  日期：2012.9

  The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl2/phen/Ag2CO3/K3PO4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core. (C) 2012 Elsevier Ltd. All rights reserved.