6-methoxy-2-phenylisoindolin-1-one | 33886-52-1

• 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: 6-methoxy-2-phenylisoindolin-1-one
• 英文别名: 6-methoxy-2-phenyl-3H-isoindol-1-one
• CAS: 33886-52-1
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: KNCKXHMWOVZIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  5-methoxy-2-methyl-N-phenylbenzamide 在 4-二甲氨基吡啶 、 copper(l) iodide 、 二叔丁基过氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到6-methoxy-2-phenylisoindolin-1-one
  参考文献：
  名称：

  Copper-Catalyzed sp³ C–H Aminative Cyclization of 2-Alkyl-N-arylbenzamides: An Approach for the Synthesis of N-Aryl-isoindolinones

  摘要：

  The synthesis of isoindolinones via copper-catalyzed sp(3) C-H functionalization of 2-alkyl-N-substituted benzamides is described. This process does not require the preparation of halogenated substitutes, expensive transition metals, or toxic Sn or CO gas. This method provides an efficient approach to generate various functionalized isoindolinones.

  DOI：

  10.1021/acs.orglett.5b02235

文献信息

• Preparation of phthalimidines
  申请人：DU PONT

  公开号：US02841591A1

  公开（公告）日：1958-07-01
• Direct Access to Benzolactams and Benzolactones via Nickel Catalyzed Carbonylation with CO2
  作者：Riccardo Giovanelli、Giulia Monda、Sofia Kiriakidi、Carlos Silva López、Giulio Bertuzzi、Marco Bandini

  DOI：10.1002/chem.202401658

  日期：2024.8.22

  A new nickel catalyzed cross‐electrophile coupling for accessing γ‐lactams (isoindolinones) as well as γ‐lactones (isobenzofuranones) via carbonylation with CO2 is documented. The protocol exploits the synergistic role of redox‐active Ni(II) complexes and AlCl3 as a CO2 activator/oxygen scavenger, leading to the formation of a wide range of cyclic amides and esters (28 examples) in good to high yields (up to 87%). A dedicated computational investigation revealed the multiple roles played by AlCl3. In particular, the simultaneous transient protection of the pendant amino group of the starting reagents and the formation of the electrophilically activated CO2‐AlCl3 adduct are shown to concur in paving the way for an energetically favorable mechanistic pathway.