7-methyl-3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one | 1604839-56-6

• 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: 7-methyl-3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
• CAS: 1604839-56-6
• 化学式: C₃₁H₂₂N₂O
• 分子量: 438.528
• InChiKey: PWEOMNAZCJWIKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-(3-methylbenzoyl)-8-aminoquinoline 、 二苯基乙炔 在 [(p-cymene)RuCl₂]₂ 、 copper(II) acetate monohydrate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 24.0h， 以67%的产率得到7-methyl-3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Synthesis of Isoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C–H Functionalization

  摘要：

  Ruthenium-catalyzed oxidative annulation of N-quinolin-8-yl-benzamides with alkynes in open air has been achieved using 8-aminoquinolinyl moiety as a bidentate directing group in the presence of Cu(OAc)(2)center dot H2O as an oxidant. This reaction offers a broad substrate scope, and both symmetrical and unsymmetrical alkynes can be applied. High regioselectivity was achieved in the case of unsymmetrical (aryl)alkynes. Reaction with heteroaryl amides was also successful in this catalytic process. A ruthenium-N-quinolin-8-yl-benzamide complex was isolated in the absence of alkyne; in the absence of both N-quinolin-8-yl-benzamide and alkyne, in contrast to literature, only the monoacetate complex RuCl(OAc)(p-cymene), but not the bis-acetate complex Ru(OAc)2(p-cymene), was isolated. These data suggest that this reaction may proceed via N,N-bidentate chelate complex. Key products were characterized by X-ray crystallography.

  DOI：

  10.1021/jo500424p

文献信息

• Rhodium-catalyzed synthesis of substituted isoquinolones <i>via</i> a selective decarbonylation/alkyne insertion cascade of phthalimides
  作者：Fen Xu、Wen-Jing Zhu、Juan Wang、Qi Ma、Li-Jing Shen

  DOI：10.1039/d0ob01793k

  日期：——

  A rhodium-catalyzed decarbonylation/alkyne insertion cascade of phthalimides has been established. The reaction can be carried out in an operationally simple manner and provides expedient access to a series of isoquinolones in moderate to good yields. This reaction proceeded through a sequential decarbonylation/alkyne insertion/intramolecular annulation procedure and featured good functional group

  已经建立了铑催化的邻苯二甲酰亚胺脱羰基/炔烃插入级联。该反应可以以操作简单的方式进行，并以中等至良好的产率方便地获得一系列异喹诺酮类药物。该反应通过顺序脱羰/炔烃插入/分子内环化过程进行，具有良好的官能团耐受性、充足的底物范围以及一锅中C-C和C-N键的构建。