4-methyl-3-phenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one | 1604839-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-methyl-3-phenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
• 英文别名: 4-Methyl-3-phenyl-2-quinolin-8-ylisoquinolin-1-one
• CAS: 1604839-43-1
• 化学式: C₂₅H₁₈N₂O
• 分子量: 362.431
• InChiKey: SCYSCIPSRKFGMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  8-氨基喹啉 在 4-二甲氨基吡啶 、 manganese(II) acetate 、 cobalt(II) diacetate tetrahydrate 、 特戊酸钠 、 三乙胺 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 16.0h， 生成 4-methyl-3-phenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  钴催化的氨基喹啉引导的炔烃 C(sp2)?H 键烯基化

  摘要：

  开发了一种钴催化、氨基喹啉和吡啶酰胺引导的炔烃 C(sp 2 )  H 键烯基化方法。该方法显示出优异的官能团耐受性，内部和末端炔烃都是偶联的有效底物。该反应采用Co(OAc) 2 ⋅4 H 2 O催化剂、Mn(OAc) 2助催化剂和氧气（来自空气）作为终端氧化剂。

  DOI：

  10.1002/anie.201404579

文献信息

• Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C–N and C–C Bonds
  作者：Xiang-Ting Min、Ding-Wei Ji、Hao Zheng、Bing-Zhi Chen、Yan-Cheng Hu、Boshun Wan、Qing-An Chen

  DOI：10.1021/acs.orglett.0c00875

  日期：2020.5.1

  Through the oxidative addition of cobalt into the N-C(O) bond of phthalimide and the subsequent decarbonylation, we describe an efficient cobalt-catalyzed intermolecular decarbonylative carboamidation of alkynes. High regioselectivities have been achieved for unsymmetrical alkynes (including aryl-alkyl or aryl-aryl) to deliver polysubstituted isoquinolones. To facilitate step economy, a three-component

  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。
• 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。
• 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.