2-(quinolin-8-yl)-3,4-bis(4-(trifluoromethyl)phenyl)isoquinolin-1(2H)-one | 1604839-37-3

• 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-(quinolin-8-yl)-3,4-bis(4-(trifluoromethyl)phenyl)isoquinolin-1(2H)-one
• CAS: 1604839-37-3
• 化学式: C₃₂H₁₈F₆N₂O
• 分子量: 560.498
• InChiKey: CMSPCUGMWYRBNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.91
• 重原子数：
  41.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  苯酐 在 三(2-甲氧基苯基)膦 、 溶剂黄146 、 silver carbonate 、 cobalt(II) iodide 作用下， 以 邻二氯苯 为溶剂， 反应 48.0h， 生成 2-(quinolin-8-yl)-3,4-bis(4-(trifluoromethyl)phenyl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  通过CN和CC键的裂解实现的钴催化的含炔的炔烃区域选择性碳酰胺化反应。

  摘要：

  通过氧化钴到邻苯二甲酰亚胺的NC（O）键中的氧化和随后的脱羰作用，我们描述了炔烃的有效钴催化的分子间脱羰碳酰胺化作用。对于不对称炔烃（包括芳基-烷基或芳基-芳基）可以实现高区域选择性，以递送多取代的异喹诺酮。为了促进步骤经济，目前的钴催化技术已证明炔烃与邻苯二甲酸酐和胺的三组分脱羰碳酰胺化反应。

  DOI：

  10.1021/acs.orglett.0c00875

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。
• Chemodivergent Nickel(0)-Catalyzed Arene C–F Activation with Alkynes: Unprecedented C–F/C–H Double Insertion
  作者：Lorena Capdevila、Tjark H. Meyer、Steven Roldán-Gómez、Josep M. Luis、Lutz Ackermann、Xavi Ribas

  DOI：10.1021/acscatal.9b03620

  日期：2019.12.6

  allowed the selective synthesis of double-insertion aromatic homologation or alkyne monoannulation products by C–F/C–H activation. On the basis of the unambiguous crystallographic characterization of an unprecedented nine-membered nickelacyclic intermediate and extensive DFT studies, a plausible mechanistic rationale was established for the selective C–F activation and the chemodivergent catalysis.

  镍催化的CF活化通过螯合协助与炔烃形成化学趋异的CC形成。对炔电子性质的明智选择允许通过C–F / C–H活化选择性合成双插入芳族同系物或炔单环合物。基于前所未有的九元镍环中间体和广泛DFT研究的明确晶体学表征，建立了选择性CF活化和化学发散催化作用的合理机理。
• Ruthenium-Catalyzed Synthesis of Isoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C–H Functionalization
  作者：Srinivasarao Allu、K. C. Kumara Swamy

  DOI：10.1021/jo500424p

  日期：2014.5.2

  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.