(E)-2-benzyl-3-(4-methoxybenzylidene)isoindolin-1-one | 1242025-84-8

• 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: (E)-2-benzyl-3-(4-methoxybenzylidene)isoindolin-1-one
• 英文别名: (3E)-2-benzyl-3-(4-methoxybenzylidene)isoindolin-1-one；(3E)-2-benzyl-3-[(4-methoxyphenyl)methylidene]isoindol-1-one
• CAS: 1242025-84-8
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: VTYPLGRQMHSMFM-PXLXIMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-benzyl-3-methyleneisoindolin-1-one 在 lithium carbonate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.33h， 生成 (E)-2-benzyl-3-(4-methoxybenzylidene)isoindolin-1-one
  参考文献：
  名称：

  Base‐ and Visible‐Light‐Promoted Formation of 3‐Benzyl‐3‐Methoxyisoindolin‐1‐one

  摘要：

  Aryl diazonium salts are versatile compounds known for their reactivity in various transformations. In this study, we explored the arylation of 3‐methylene isoindolinones using aryl diazonium salts. The objective was to develop a method for accessing 3‐benzyl‐3‐methoxyisoindolin‐1‐ones, a class of compounds with diverse biological activities and synthetic importance. Optimization of the reaction conditions revealed the significance of light irradiation for improved yields. The substrate scope investigation demonstrated the compatibility of various diazonium salts and N‐substituents on the 3‐methylene isoindolinone scaffold, yielding the corresponding methoxy lactams with high yields. Mechanistic insights were obtained by observing the effect of base and light irradiation. Two initiation mechanisms were proposed: in the presence of a base, the reaction could proceed even without light irradiation, while light irradiation was necessary in the absence of a base. DFT calculations were performed to elucidate the mechanism of the reaction and provide energetic considerations

  DOI：

  10.1002/ejoc.202400025

文献信息

• Product Selectivity Control in the Heteroannulation of<i>o</i>-(1-Alkynyl)benzamides
  作者：Gabriele Bianchi、Marco Chiarini、Fabio Marinelli、Leucio Rossi、Antonio Arcadi

  DOI：10.1002/adsc.200900668

  日期：2010.1.4

  The selective synthesis of (Z)‐ or (E)‐3‐aryl/vinyl/alkylidene‐isoindolones, and 2‐benzopyran derivatives from o‐(1‐alkynyl)benzamides by means of a suitable choice of bases or silver catalysis is described.

  的选择性合成（ż） -或（Ë）-3-芳基/乙烯基/亚烷基-异吲哚酮，和由2-苯并吡喃衍生物Ö - （1-炔基）苯甲酰胺通过碱或银催化的适当选择的装置进行说明。