2-(5-oxo-12-phenyl-5,7-dihydroisoindolo[2,1-b]isoquinolin-7-yl)acetonitrile | 1280681-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(5-oxo-12-phenyl-5,7-dihydroisoindolo[2,1-b]isoquinolin-7-yl)acetonitrile
• 英文别名: 2-(5-oxo-12-phenyl-7H-isoindolo[2,1-b]isoquinolin-7-yl)acetonitrile
• CAS: 1280681-76-6
• 化学式: C₂₄H₁₆N₂O
• 分子量: 348.404
• InChiKey: NLEHUVSFIXYIRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-diphenyl-2H-isoquinolin-1-one 、 丙烯腈 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以71%的产率得到2-(5-oxo-12-phenyl-5,7-dihydroisoindolo[2,1-b]isoquinolin-7-yl)acetonitrile
  参考文献：
  名称：

  铱催化的 NH 异喹诺酮类与烯烃的氧化偶联和环化反应生成 isoindolo[2,1-b]isoquinolin-5(7H)-one 衍生物

  摘要：

  已经实现了铱催化的NH异喹诺酮与烯烃的氧化偶联和环化。大多数异吲哚[2,1- b ]isoquinolin-5(7H)-one 衍生物以中等至良好的产率获得。还进行了几个衍生反应，包括官能团转化和进一步的 C H /烯烃偶联。这种转化实现了较少开发的 Cp*Ir(III) 催化的 NH 底物与烯烃的偶联和环化反应。

  DOI：

  10.1016/j.tetlet.2022.153779

文献信息

• Oxidative Coupling of NH Isoquinolones with Olefins Catalyzed by Rh(III)
  作者：Fen Wang、Guoyong Song、Zhengyin Du、Xingwei Li

  DOI：10.1021/jo2002209

  日期：2011.4.15

  Rh(III)-catalyzed oxidative coupling reactions between isoquinolones with 3-aryl groups and activated olefins have been achieved using anhydrous Cu(OAc)(2) as an oxidant to give tetracyclic products. The nitrogen atom acts as a directing group to facilitate ortho C-H activation. This reaction can be one-pot starting from methyl benzohydroxamates, without the necessity of the isolation of isoquinolone products. Abroad scope of substrates has been demonstrated, and both terminal and internal activated olefins can be applied. In the coupling of N-methylmaleimide, a Wacker-like mechanism was proposed, where backside attack of the NH group in isoquinolones is suggested as a key step. Selective C-H activation has also been achieved at the 8-position of 1-naphthol, leading to an olefination product.
• Iridium-catalyzed oxidative coupling and cyclization of NH isoquinolones with olefins leading to isoindolo[2,1-b]isoquinolin-5(7H)-one derivatives
  作者：Kelu Yan、Xiao Liu、Min Liu、Jiangwei Wen、Mingyue Du、Yingxue Fu、Wenxin Chen

  DOI：10.1016/j.tetlet.2022.153779

  日期：2022.5

  coupling and cyclization of NH isoquinolones with olefins has been realized. Most isoindolo[2,1-b]isoquinolin-5(7H)-one derivatives were obtained in moderate to good yields. Several derivatization reactions including functional group conversion and further CH/olefin coupling were also performed. This transformation realized the less developed Cp*Ir(III) catalyzed coupling and cyclization reaction of

  已经实现了铱催化的NH异喹诺酮与烯烃的氧化偶联和环化。大多数异吲哚[2,1- b ]isoquinolin-5(7H)-one 衍生物以中等至良好的产率获得。还进行了几个衍生反应，包括官能团转化和进一步的 C H /烯烃偶联。这种转化实现了较少开发的 Cp*Ir(III) 催化的 NH 底物与烯烃的偶联和环化反应。