3-benzyl-2-phenylisoindolin-1-one | 4679-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-benzyl-2-phenylisoindolin-1-one
• 英文别名: 1h-Isoindol-1-one,2,3-dihydro-2-phenyl-3-(phenylmethyl)-；3-benzyl-2-phenyl-3H-isoindol-1-one
• CAS: 4679-90-7
• 化学式: C₂₁H₁₇NO
• 分子量: 299.372
• InChiKey: HZRLRFACCKGGGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z)-2-苯基-3-(苯基亚甲基)异吲哚啉-1-酮 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 24.0h， 生成 3-benzyl-2-phenylisoindolin-1-one
  参考文献：
  名称：

  Palladium-Catalysed Heteroannulation with Terminal Alkynes: a Highly Regio- and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones

  摘要：

  A highly regio- and stereoselective method for the synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)(2)PdCl2, CuI, and Et3N in DMF mostly at 80 degrees C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00359-8

文献信息

• Intramolecular Hydroamidation of <i>ortho</i> -Vinyl Benzamides Promoted by Potassium <i>tert</i> -Butoxide/<i>N,N</i> -Dimethylformamide
  作者：Zhen-yu Chen、Liang-yu Wu、Hai-sheng Fang、Ting Zhang、Zhi-feng Mao、Yong Zou、Xue-jing Zhang、Ming Yan

  DOI：10.1002/adsc.201700369

  日期：2017.11.23

  An intramolecular hydroamidation of ortho-vinyl benzamides had been developed. The reaction was promoted efficiently by potassium tert-butoxide and N,N-dimethylformamide without the need for strong oxidants or transition-metal catalysts. A series of dihydroisoquinolinones and 3-benzylisoindolinones were prepared in good to excellent yields. The new method is operationally simple, scalable, and tolerant

  已经开发了邻乙烯基苯甲酰胺的分子内加氢酰胺化。叔丁醇钾和N，N-二甲基甲酰胺可有效促进反应，而无需强氧化剂或过渡金属催化剂。制备了一系列二氢异喹啉酮和3-苄基异吲哚啉酮，收率良好至优异。新方法在操作上简单，可扩展并且可以容忍各种功能组。
• Novel Chemoselective Desulfurization of γ-Phenylthio-Substituted Aromatic Lactams: Application to the Synthesis of Isoindolobenzazepine Alkaloid, Lennoxamine
  作者：Hidemi Yoda、Takamasa Suzuki、Kunihiko Takabe

  DOI：10.1055/s-2006-956452

  日期：2006.12

  Treatment of a variety of γ-phenylthio-substituted aromatic lactams with lithium aluminum hydride in the presence of cuprous iodide led to novel chemoselective desulfurization reactions to afford the corresponding substituted aromatic lactams without giving the carbonyl-reduced and/or ring-opened products in extremely high yields. This process was further applied to the total synthesis of an isoindolobenzazepine alkaloid, lennoxamine, by featuring the elaboration of the functionalized phthalimide derivative.

  在碘化亚铜存在下，用氢化铝锂处理各种δ-苯硫基取代的芳香族内酰胺，可产生新的化学选择性脱硫反应，从而得到相应的取代芳香族内酰胺，且不产生羰基还原和/或开环产物，收率极高。这一工艺还被进一步应用于异吲哚苯并氮杂卓生物碱--伦诺沙明的全合成，其特点是可以制备功能化邻苯二甲酰亚胺衍生物。
• Electrochemical reductive cascade cyclization of <i>o</i>-alkynylated derivatives for saturated amides/amines
  作者：Mandapati Bhargava Reddy、Sakthivel Prabhu、Ramasamy Anandhan

  DOI：10.1039/d3cc03350c

  日期：——

  An unprecedented reductive hydroamidative/hydroquinazolinative cascade cyclization of o-alkynylated derivatives was achieved via proton-coupled electron transfer (PCET) under electrolysis. In a single step, the rapid assembly of isoindolinones and novel isoindole-fused quinazolinones were achieved through electrolysis by the hydroamidation of amidyl/quinazolinone aminyl radicals with C–C triple bond

  通过电解下的质子耦合电子转移（PCET）实现了邻炔基化衍生物前所未有的还原氢酰胺化/氢喹唑啉级联环化。通过电解，通过酰胺基/喹唑啉酮氨基自由基与 C-C 三键加成，通过 5-exo-dig 环化，然后进行烯属还原，一步完成异吲哚酮和新型异吲哚稠合喹唑啉酮的快速组装，无需外部还原剂。控制和循环伏安实验支持电化学级联的机械解释，这些实验表明电解质是烯烃还原的氢源。
• Palladium-Catalysed Heteroannulation with Terminal Alkynes: a Highly Regio- and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones
  作者：Nitya G Kundu、M.Wahab Khan

  DOI：10.1016/s0040-4020(00)00359-8

  日期：2000.6

  A highly regio- and stereoselective method for the synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)(2)PdCl2, CuI, and Et3N in DMF mostly at 80 degrees C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.