2-benzyl-5-methoxylisoquinolin-1(2H)-one | 1115276-81-7

• 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: 2-benzyl-5-methoxylisoquinolin-1(2H)-one
• 英文别名: 2-Benzyl-5-methoxyisoquinolin-1-one
• CAS: 1115276-81-7
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: IPOFKMZZLGQQDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 2-benzyl-5-methoxylisoquinolin-1(2H)-one 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 溶剂黄146 作用下， 以99 %的产率得到
  参考文献：
  名称：

  Chemo selective C-H alkylation of isoquinolones with maleimides: A combined experimental and computational case study

  摘要：

  DOI：

  10.1016/j.mcat.2023.113597
• 作为产物：
  描述：

  2-chloro-3-methoxy-N-benzylbenzamide 、 2,5-降冰片二烯 在 palladium diacetate 、 caesium carbonate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 以43%的产率得到2-benzyl-5-methoxylisoquinolin-1(2H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles

  摘要：

  A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.

  DOI：

  10.1021/jo802604g

文献信息

• Rhodium‐Catalyzed C8‐Alkenylation of Isoquinolones with Maleimides
  作者：Manisha、Devesh Chandra、Upendra Sharma

  DOI：10.1002/ejoc.202300411

  日期：2023.8.7

  Selective olefination of N-protected isoquinolones at C8-position has been achieved under rhodium catalysis. A range of maleimides were employed to obtain the olefinated products in moderate to excellent yield with excellent selectivity. Kinetic Isotope Effect (KIE) study and Hammett plot analysis were also performed to understand the reaction mechanism.

  在铑催化下，实现了C8位N-保护的异喹诺酮的选择性烯化。采用一系列马来酰亚胺以中等至优异的产率和优异的选择性获得烯化产物。还进行了动力学同位素效应（KIE）研究和哈米特图分析以了解反应机理。
• 10.1039/d4ob01084a
  作者：Thakur, Ankita、Chandra, Devesh、Sharma, Upendra

  DOI：10.1039/d4ob01084a

  日期：——

  A simple and rapid access to isoquinolone aldehyde scaffolds has been established by a rhodium-catalyzed reaction between isoquinolone and methoxyallene that forges alkenylation in an explicit regioselective manner. Herein, methoxyallene serving as an acrolein equivalent results in execution of this unique functionalization. Furthermore, the compatibility with complex molecules underscores the significance

  通过异喹诺酮和甲氧基丙二烯之间的铑催化反应，以明确的区域选择性方式形成烯基化，建立了一种简单快速的异喹诺酮醛支架的获取方法。在此，甲氧基丙二烯作为丙烯醛等价物导致执行这种独特的官能化。此外，与复杂分子的兼容性强调了该开发协议的重要性。这种区域选择性转化的机制建议与动力学研究和几个控制反应一致。
• Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles
  作者：Praew Thansandote、David G. Hulcoop、Michael Langer、Mark Lautens

  DOI：10.1021/jo802604g

  日期：2009.2.20

  A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.
• Chemo selective C-H alkylation of isoquinolones with maleimides: A combined experimental and computational case study
  作者：Devesh Chandra、Nikunj Kumar、Sumit、Puneet Gupta、Upendra Sharma

  DOI：10.1016/j.mcat.2023.113597

  日期：2023.12