(2-Chlorophenyl)-(2-phenyldiazenylphenyl)methanone | 1421276-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-Chlorophenyl)-(2-phenyldiazenylphenyl)methanone
• 英文别名: (2-chlorophenyl)-(2-phenyldiazenylphenyl)methanone
• CAS: 1421276-28-9
• 化学式: C₁₉H₁₃ClN₂O
• 分子量: 320.778
• InChiKey: CTAQGALWSPKHQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-Chlorophenyl)-(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-(2-chlorophenyl)-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
• 作为产物：
  描述：

  苯胺 在 叔丁基过氧化氢 、 palladium diacetate 、 copper(I) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 (2-Chlorophenyl)-(2-phenyldiazenylphenyl)methanone
  参考文献：
  名称：

  Direct Access to Acylated Azobenzenes via Pd-Catalyzed C–H Functionalization and Further Transformation into an Indazole Backbone

  摘要：

  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.

  DOI：

  10.1021/ol303434n

文献信息

• A Highly Efficient Palladium-Catalyzed Decarboxylative<i>ortho</i>-Acylation of Azobenzenes with α-Oxocarboxylic Acids: Direct Access to Acylated Azo Compounds
  作者：Hongji Li、Pinhua Li、Hui Tan、Lei Wang

  DOI：10.1002/chem.201301818

  日期：2013.10.18

  Avoiding additives: A highly efficient and mild Pd‐catalyzed decarboxylative ortho‐acylation of azobenzenes with α‐oxocarboxylic acids was developed that provides an alternative route to acylated azo compounds. This decarboxylative acylation process was completed in the absence of any additives at ambient temperature, to afford the acylated azobenzenes in moderate to good yields (see scheme).

  避免添加剂：A高效和温和的Pd-催化的脱羧邻用α-氧代羧酸偶氮苯的酰化的开发，提供了酰化的偶氮化合物的替代路线。在环境温度下在不存在任何添加剂的情况下完成该脱羧酰化过程，以中等至良好的产率得到酰化的偶氮苯（参见方案）。
• 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.
• 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。