3,4-bis(4-chlorophenyl)-2-(quinolin-8-yl)isoquinolin-1(2H)-one | 1604839-36-2

• 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: 3,4-bis(4-chlorophenyl)-2-(quinolin-8-yl)isoquinolin-1(2H)-one
• CAS: 1604839-36-2
• 化学式: C₃₀H₁₈Cl₂N₂O
• 分子量: 493.392
• InChiKey: CXTOLMLHMMWRJG-UHFFFAOYSA-N

物化性质

• 熔点：
  174.4-175.8 °C
• 沸点：
  666.9±55.0 °C(predicted)
• 密度：
  1.382±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 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 3,4-bis(4-chlorophenyl)-2-(quinolin-8-yl)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

• 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。
• 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。
• 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.