2-benzyl-3-phenyl-2H-indazole | 54449-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-benzyl-3-phenyl-2H-indazole
• 英文别名: 2-Benzyl-3-phenylindazol；2-Benzyl-3-phenylindazole
• CAS: 54449-01-3
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: FMQIBUNZYSQGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  2-benzyl-3-phenyl-2H-indazole 、 1-benzyl-3-phenyl-1H-indazole 在 potassium tert-butylate 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 5.0h， 以25 mg的产率得到3-苯基-1H-吲唑
  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
• 作为产物：
  描述：

  氯化苄 在 potassium phosphate 、 1,10-菲罗啉 、 sodium hydride 、 silver carbonate 、 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 14.33h， 生成 2-benzyl-3-phenyl-2H-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

• Direct C3-Arylation of 2 <i>H</i> -Indazole Derivatives with Aryl Bromides by using Low Loading of a Phosphine-free Palladium Catalyst
  作者：Fatma Belkessam、Mohand Aidene、Jean-François Soulé、Henri Doucet

  DOI：10.1002/cctc.201601420

  日期：2017.6.22

  The palladium-catalyzed direct arylation of 2 H-indazoles with aryl bromides for the preparation of 3-aryl-2 H-indazoles was found to proceed in high yields when using only 0.5–0.1 mol % Pd(OAc)2 catalyst and KOAc as inexpensive base. A wide variety of electron-deficient and electron-rich aryl bromides and also heteroaryl bromides has been successfully employed. Both electron-withdrawing and electron-donating

  当仅使用0.5–0.1 mol％Pd（OAc）2催化剂和KOAc作为钯时，发现钯催化的2 H-吲唑与芳基溴的直接芳基化反应可 制备3-芳基2  H-吲唑。便宜的基地。已经成功地使用了各种各样的缺电子和富电子的芳基溴化物以及杂芳基溴化物。2 H-吲唑上的吸电子和供电子取代基 也被容许。此外，反应可以在“绿色”溶剂环戊基甲基醚中进行。
• KATO H.; NAKAZAWA S.; KIYOSAWA T.; HIRAKAWA K., J. CHEM. SOC. PERKIN TRANS., PART 1 <JCPK-BH>, 1976, NO 6, 672-675
  作者：KATO H.、 NAKAZAWA S.、 KIYOSAWA T.、 HIRAKAWA K.

  DOI：——

  日期：——
• CN115124472
  申请人：——

  公开号：——

  公开（公告）日：——