4',5-dimethylbiphenyl-2-carboxamide | 1370411-31-6

• 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: 4',5-dimethylbiphenyl-2-carboxamide
• 英文别名: 4-Methyl-2-(4-methylphenyl)benzamide
• CAS: 1370411-31-6
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: IDPYENMJMHUWPJ-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4',5-dimethylbiphenyl-2-carboxamide 在 copper(l) iodide 、 potassium tert-butylate 、 氧气 、 三苯基膦 作用下， 以 邻二甲苯 为溶剂， 反应 18.0h， 以75%的产率得到3,9-dimethylphenanthridin-6(5H)-one
  参考文献：
  名称：

  Synthesis of Phenanthridin-6(5H)-ones via Copper-Catalyzed Cyclization of 2-Phenylbenzamides

  摘要：

  Synthesis of phenanthridin-6(5H)-ones was achieved via copper-catalyzed cyclization of 2-phenylbenzamides using air as the oxidant and KOt-Bu as the base. It was discovered that, besides Ph3P, other ligands such as 1,10-phenanthroline, TMEDA as well as L-proline could also be used as the ligand to effect the transformation.

  DOI：

  10.1055/s-0032-1316898
• 作为产物：
  描述：

  4-碘甲苯 、 对甲苯酰胺 在 palladium diacetate 、 silver(l) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以50%的产率得到4',5-dimethylbiphenyl-2-carboxamide
  参考文献：
  名称：

  Palladium-Catalyzed Ortho-Arylation of Benzamides via Direct sp²C–H Bond Activation

  摘要：

  The palladium-catalyzed ortho-arylation of benzamides by aryl iodides has been demonstrated with the simplest amide CONH2 as a directing group for the first time. This protocol can be applied to various benzamides and aryl iodides with both electron-donating and electron-withdrawing groups. In addition, the synthesized biphenyl-2-carboxamides can be further transformed to other biphenyl derivatives such as nitriles, carboxylic acids, carbamates, and amines.

  DOI：

  10.1021/jo300126n

文献信息

• Palladium-Catalyzed Ortho-Arylation of Benzamides via Direct sp²C–H Bond Activation
  作者：Dan-Dan Li、Ting-Ting Yuan、Guan-Wu Wang

  DOI：10.1021/jo300126n

  日期：2012.4.6

  The palladium-catalyzed ortho-arylation of benzamides by aryl iodides has been demonstrated with the simplest amide CONH2 as a directing group for the first time. This protocol can be applied to various benzamides and aryl iodides with both electron-donating and electron-withdrawing groups. In addition, the synthesized biphenyl-2-carboxamides can be further transformed to other biphenyl derivatives such as nitriles, carboxylic acids, carbamates, and amines.
• Synthesis of Phenanthridin-6(5H)-ones via Copper-Catalyzed Cyclization of 2-Phenylbenzamides
  作者：Ze Tan、Wei Yu、Qingwen Gui、Zhiyong Yang、Xiang Chen、Jidan Liu、Ruqing Guo

  DOI：10.1055/s-0032-1316898

  日期：——

  Synthesis of phenanthridin-6(5H)-ones was achieved via copper-catalyzed cyclization of 2-phenylbenzamides using air as the oxidant and KOt-Bu as the base. It was discovered that, besides Ph3P, other ligands such as 1,10-phenanthroline, TMEDA as well as L-proline could also be used as the ligand to effect the transformation.