2-benzyl-3-hydroxy-3-(4-methoxybenzyl)isoindolin-1-one | 879547-42-9

• 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: 2-benzyl-3-hydroxy-3-(4-methoxybenzyl)isoindolin-1-one
• CAS: 879547-42-9
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: HRJAOBNONQGXDB-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  582.1±50.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-乙酰苯甲酸 在 水 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.33h， 生成 2-benzyl-3-hydroxy-3-(4-methoxybenzyl)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

• Metal-free tandem reaction in water: An efficient and regioselective synthesis of 3-hydroxyisoindolin-1-ones
  作者：Yu Zhou、Yun Zhai、Jian Li、Deju Ye、Hualiang Jiang、Hong Liu

  DOI：10.1039/c004745g

  日期：——

  A mild and effective method was developed for the construction of heterocyclic building blocks 3-hydroxyisoindolin-1-ones via a metal-free tandem transformation with excellent regioselectivity. Significantly, the strategy presents an atom-economical and environmentally friendly transformation, in which two new C–N bonds and one C–O bond are formed in water from two simple starting materials. Moreover, a broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields.

  开发了一种温和且有效的方法，通过无金属串联转化构建杂环构件3-羟基异印度啶-1-酮，具有优异的区域选择性。值得注意的是，该策略实现了一种原子经济且环保的转化，在水中从两种简单起始材料形成两个新的C–N键和一个C–O键。此外，广泛的底物可以有效参与该过程，生成良好产率的目标产品。