2-phenyl-3-(o-tolyl)-2H-indazole | 1201938-09-1

• 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-phenyl-3-(o-tolyl)-2H-indazole
• 英文别名: 2-phenyl-3-(2-methylphenyl)-2H-indazole；3-(2-Methylphenyl)-2-phenylindazole；3-(2-methylphenyl)-2-phenylindazole
• CAS: 1201938-09-1
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: VAQFFJNHZMUYBD-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：

  (2-Methylphenyl)-(2-phenyldiazenylphenyl)methanone 在 对甲苯磺酰肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到2-phenyl-3-(o-tolyl)-2H-indazole
  参考文献：
  名称：

  甲苯磺酰肼促进的酰基偶氮苯串联缩合和环化反应使无金属好氧条件下可接触2H-吲唑

  摘要：

  甲苯磺酰肼促进的串联缩合反应和2-酰基偶氮苯在无金属的好氧条件下的环化反应可通过释放水以定量收率得到在3位具有烷基或芳基的2-芳基2 H-吲唑，分子氮和亚磺酸。所有实施例均以定量产率产生了相应的2 H-吲唑。确定本反应具有宽的底物范围和良好的官能团耐受性。

  DOI：

  10.1002/adsc.201801055

文献信息

• Direct Arylations of 2<i>H</i>-Indazoles On Water
  作者：Stephan A. Ohnmacht、Andrew J. Culshaw、Michael F. Greaney

  DOI：10.1021/ol902537d

  日期：2010.1.15

  The efficient palladium-catalyzed synthesis of a range of substituted 2H-Indazoles via C−H arylation is reported. Reactions are performed on water and provide a direct and mild route toward 2,3-diaryl indazoles of widespread biological significance.

  据报道，通过CHH芳基化反应，钯可以有效地合成一系列取代的2 H-吲唑。反应在水上进行，提供了直接而温和的路线，向具有广泛生物学意义的2，3-二芳基吲唑提供了途径。
• Continuous‐Flow Visible Light Organophotocatalysis for Direct Arylation of 2 <i>H</i> ‐Indazoles: Fast Access to Drug Molecules
  作者：Shinde Vidyacharan、Bandaru T. Ramanjaneyulu、Seungwook Jang、Dong‐Pyo Kim

  DOI：10.1002/cssc.201900736

  日期：2019.6.21

  A continuous‐flow homogeneous photocatalytic method has been devised for the direct arylation of 2H‐indazoles. This visible‐light‐promoted approach directly accesses a wide range of structurally diverse C3‐arylated scaffolds of biological interest in a fast (1 min), single‐step reaction by using eosin Y as an organophotocatalyst. Furthermore, a microreactor technology is also employed for the fast

  设计了一种连续流均相光催化方法，用于2 H-吲唑的直接芳基化。通过使用曙红Y作为有机光催化剂，这种可见光促进的方法可以快速（1分钟），一步式反应直接访问各种具有生物意义的结构多样的C3芳基化支架。此外，微反应器技术还用于在无金属条件下以很高的收率快速合成肝X受体抑制剂药物，而已报道的方法需要多个步骤并需要更长的反应时间（18-24小时）。
• Direct Access to Acylated Azobenzenes via Pd-Catalyzed C–H Functionalization and Further Transformation into an Indazole Backbone
  作者：Hongji Li、Pinhua Li、Lei Wang

  DOI：10.1021/ol303434n

  日期：2013.2.1

  Azobenzenes were readily acylated at the 2-position through a Pd-catalyzed C-H functionalization from simple aromatic azo compounds and aldehydes in good yields. The obtained acylated azobenzenes could be efficiently converted into the corresponding indazole derivatives in nearly quantitative yields.
• 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.
• Tosyl Hydrazine-Promoted Tandem Condensation and Cyclization of Acyl Azobenzenes Enabling Access to 2<i>H</i> -Indazoles under Metal-Free Aerobic Conditions
  作者：Jeong-Yu Son、Hyunseok Kim、Yonghyeon Baek、Kyusik Um、Gi Hoon Ko、Gi Uk Han、Sang Hoon Han、Kooyeon Lee、Phil Ho Lee

  DOI：10.1002/adsc.201801055

  日期：2018.11.16

  Tosyl hydrazine‐promoted tandem condensation and cyclization of 2‐acyl azobenzenes under metal‐free aerobic conditions was demonstrated to give 2‐aryl‐2H‐indazoles having alkyl‐ or aryl groups at the 3‐position in quantitative yields through the release of water, molecular nitrogen, and sulfinic acid. All of the examples produced the corresponding 2H‐indazoles in quantitative yields. The present reaction

  甲苯磺酰肼促进的串联缩合反应和2-酰基偶氮苯在无金属的好氧条件下的环化反应可通过释放水以定量收率得到在3位具有烷基或芳基的2-芳基2 H-吲唑，分子氮和亚磺酸。所有实施例均以定量产率产生了相应的2 H-吲唑。确定本反应具有宽的底物范围和良好的官能团耐受性。