4-ethyl-3-phenylisoquinolin-1(2H)-one

• 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: 4-ethyl-3-phenylisoquinolin-1(2H)-one
• 英文别名: 4-ethyl-3-phenyl-2H-isoquinolin-1-one
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: MBJUWZWWDDQJSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-氯代苯甲酰胺 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 zinc diacetate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 4-ethyl-3-phenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  Sulfilimines as Transformable and Retainable Directing Groups in Rhodium-Catalyzed ortho-C–H Bond Functionalization

  摘要：

  DOI：

  10.1021/acs.orglett.2c02630

文献信息

• Redox-Neutral [4 + 2] Annulation of <i>N</i>-Methoxybenzamides with Alkynes Enabled by an Osmium(II)/HOAc Catalytic System
  作者：Jian Yang、Liexin Wu、Huiying Xu、Hui Gao、Zhi Zhou、Wei Yi

  DOI：10.1021/acs.orglett.9b03827

  日期：2019.12.20

  C-H activation strategy, an efficient osmium(II)-catalyzed redox-neutral [4 + 2] annulation of N-methoxybenzamides with alkynes has been accomplished. Computational and experimental studies revealed that such transformation leading to the synthesis of the isoquinolone core might follow an Os(II)-Os(IV)-Os(II) catalytic pathway, in which an unusual HOAc-assisted oxidative addition of osmium(II) into

  通过使用直接的CH活化策略，已实现了有效的（II）催化的炔烃与N-甲氧基苯甲酰胺的氧化还原中性[4 + 2]环化反应。计算和实验研究表明，这种导致异喹诺酮核心合成的转变可能遵循Os（II）-Os（IV）-Os（II）催化途径，其中不寻常的HOAc辅助氧化addition（II）进入NO键生成generate（IV）物种是关键的过渡态之一。对于其他线性或环状产物的一锅法组装，也已举例说明了由（II）催化剂实现的不同的CH活化反应模式的进一步探索。
• Direct Access to Cobaltacycles via C–H Activation: <i>N</i>-Chloroamide-Enabled Room-Temperature Synthesis of Heterocycles
  作者：Xiaolong Yu、Kehao Chen、Shan Guo、Pengfei Shi、Chao Song、Jin Zhu

  DOI：10.1021/acs.orglett.7b02632

  日期：2017.10.6

  Cobaltacycle synthesis via C–H activation has been achieved for the first time, providing key mechanistic insight into cobalt catalytic chemistry. N-Chloroamides are used as a directing synthon for cobalt-catalyzed room-temperature C–H activation and construction of heterocycles. Alkynes as coupling partners allow convenient access to isoquinolones, a class of synthetically and pharmaceutically important

  首次通过C–H活化合成钴环化合物，提供了对钴催化化学的关键机理的见解。N-氯酰胺用作钴催化的室温C–H活化和杂环构建的直接合成子。炔烃作为偶联伙伴可以方便地获得异喹诺酮，这是一类重要的合成和药学上重要的化合物。广泛的底物范围使得可以将各种各样的取代模式结合到杂环支架中。
• Pd-catalysed synthesis of isoquinolinones and analogues via C–H and N–H bonds double activation
  作者：Hongban Zhong、Dan Yang、Songqing Wang、Jianhui Huang

  DOI：10.1039/c2cc17859a

  日期：——

  An atom economical synthesis of isoquinolinones and analogues via ligand-free Pd-catalysed C–H and N–H double activation has been developed. A series of isoquinolinones were obtained in good to excellent yields. Good regioselectivities were also observed during the activation reactions with unsymmetrical alkynes. A practical one-pot procedure for the preparation of N–H isoquinolinones is also described.

  通过无配体钯催化的 CâH 和 NâH 双活化，开发了一种原子经济的异喹啉酮及其类似物的合成方法。一系列异喹啉酮的产率从良好到极佳。在与不对称炔烃的活化反应中也观察到了良好的区域选择性。此外，还介绍了制备 NâH 异喹啉酮的实用单锅程序。
• Ruthenium-Catalyzed C–H/N–O Bond Functionalization: Green Isoquinolone Syntheses in Water
  作者：Lutz Ackermann、Sabine Fenner

  DOI：10.1021/ol202861k

  日期：2011.12.16

  Ruthenium-catalyzed isoquinolone syntheses with ample scope were accomplished through carboxylate assistance in environmentally benign water as a reaction medium. The high chemoselectivity of the ruthenium(II) carboxylate complex also set the stage for the direct use of free hydroxamic acids for annulations of alkynes.
• A practical one-pot procedure for the synthesis of N–H isoquinolones
  作者：Shaonan Lu、Yingfu Lin、Hongban Zhong、Kang Zhao、Jianhui Huang

  DOI：10.1016/j.tetlet.2013.02.003

  日期：2013.4

  A practical one-pot procedure for the preparation of N-H isoquinolones has been developed. This 2-step process via C-H activation of N-alkoxyl benzamides and NaH-mediated dealkoxylation reaction has been demonstrated to be a high yielding alternative methodology for the efficient synthesis of a wide range of representative N-H isoquiolones. In addition, the experimental precedent supported mechanism of the dealkoxylation reaction was also proposed. (C) 2013 Elsevier Ltd. All rights reserved.