2-methyl-3,4-diphenylbenzo[g]isoquinolin-1(2H)-one | 1235478-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-methyl-3,4-diphenylbenzo[g]isoquinolin-1(2H)-one
• CAS: 1235478-97-3
• 化学式: C₂₆H₁₉NO
• 分子量: 361.443
• InChiKey: LXCJYZKGRONONR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-甲基-2-萘酸甲酰胺 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 16.0h， 以78%的产率得到2-methyl-3,4-diphenylbenzo[g]isoquinolin-1(2H)-one
  参考文献：
  名称：

  Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H Activation

  摘要：

  The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.

  DOI：

  10.1021/ja103776u

文献信息

• Ru(<scp>ii</scp>)/PEG-400 as a highly efficient and recyclable catalytic media for annulation and olefination reactions via C–H bond activation
  作者：Subhash L. Yedage、Bhalchandra M. Bhanage

  DOI：10.1039/c6gc01581f

  日期：——

  In this report synthesis of isoquinolinones, isocoumarins, N-methyl isoquinolinones and olefination of Weinreb amides by C-H bond activation using Ru(II)/PEG-400 as green and recyclable media is documented. This developed methodology...

  在该报告中，记录了异喹啉酮，异香豆素，N-甲基异喹啉酮的合成以及Weinreb酰胺通过使用Ru（II）/ PEG-400作为绿色和可回收介质的CH键活化而进行的烯化反应。这种发达的方法...