3,4-diethyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one | 1604839-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3,4-diethyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
• 英文别名: 3,4-Diethyl-2-quinolin-8-ylisoquinolin-1-one
• CAS: 1604839-40-8
• 化学式: C₂₂H₂₀N₂O
• 分子量: 328.414
• InChiKey: MXDFRNBEEHYZBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-己炔 、 8-苯甲酰基氨基喹啉 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63%的产率得到3,4-diethyl-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

• Visible Light Induced Bifunctional Rhodium Catalysis for Decarbonylative Coupling of Imides with Alkynes
  作者：Xiang‐Ting Min、Ding‐Wei Ji、Yu‐Qing Guan、Shi‐Yu Guo、Yan‐Cheng Hu、Boshun Wan、Qing‐An Chen

  DOI：10.1002/anie.202010782

  日期：2021.1.18

  Transition metal catalyzed decarbonylation offers a distinct synthetic strategy for new chemical bond formation. However, the π‐backbonding between CO π* orbitals and metal center d‐orbitals impedes ligand dissociation to regenerate the catalyst under mild reaction conditions. Developed here is visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient

  过渡金属催化的脱羰作用为新的化学键形成提供了独特的合成策略。但是，COπ*轨道与金属中心d轨道之间的π反向键会阻碍配体解离，从而在温和的反应条件下使催化剂再生。这里开发的是在环境条件下可见光诱导的铑催化，用于酰亚胺与炔烃的脱羰偶联。最初的机理研究表明，铑络合物同时充当脱羰基的催化中心和光敏剂。这种可见光促进的催化脱羰策略为审查配体解离的旧转化提供了新的机会，这是一个决定速率的步骤。
• 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。