benzyl 2-(2-bromo-5-oxo-12-phenyl-7H-isoindolo[2,1-b]isoquinolin-7-yl)acetate | 1280681-87-9

• 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: benzyl 2-(2-bromo-5-oxo-12-phenyl-7H-isoindolo[2,1-b]isoquinolin-7-yl)acetate
• CAS: 1280681-87-9
• 化学式: C₃₁H₂₂BrNO₃
• 分子量: 536.425
• InChiKey: FDRCPKGVIFYHFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-N-甲氧基苯甲酰胺 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 、 copper diacetate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 16.0h， 生成 benzyl 2-(2-bromo-5-oxo-12-phenyl-7H-isoindolo[2,1-b]isoquinolin-7-yl)acetate
  参考文献：
  名称：

  Oxidative Coupling of NH Isoquinolones with Olefins Catalyzed by Rh(III)

  摘要：

  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.

  DOI：

  10.1021/jo2002209

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.