1,2-bis(1-oxo-1,3-dihydro-isoindol-2-yl)-ethane-1,2-dione | 1268619-02-8

• 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: 1,2-bis(1-oxo-1,3-dihydro-isoindol-2-yl)-ethane-1,2-dione
• 英文别名: 1,2-bis(3-oxo-1H-isoindol-2-yl)ethane-1,2-dione
• CAS: 1268619-02-8
• 化学式: C₁₈H₁₂N₂O₄
• 分子量: 320.304
• InChiKey: SYSYNECXZVPJPE-UHFFFAOYSA-N

物化性质

• 沸点：
  531.7±60.0 °C(Predicted)
• 密度：
  1.502±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 2-碘苄胺 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、10.0 MPa 条件下， 反应 72.0h， 以54%的产率得到异吲哚啉-1-酮
  参考文献：
  名称：

  High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation

  摘要：

  1-Isoindolinone derivatives were synthesised in high yields (up to 89%) by using 2-iodobenzyl bromide and 2-iodobenzylamine as bifunctional substrates in palladium-catalysed carbonylation. Depending on the N-nucleophiles, two types of compounds were synthesised with 2-iodobenzyl bromide: the use of primary amines, including amino acid methylesters, resulted in the formation of N-substituted 1-isoindolinones, while secondary amines react both with the benzyl bromide and iodoarene moieties resulting in the corresponding ortho-(N-piperidino/morpholinomethyl)-benzamides. The parent 1-isoindolinone was obtained in a facile, highly chemoselective intramolecular aminocarbonylation of 2-iodobenzylamine. The mechanistic details of the ring-closure reaction and the conditions leading to side-products are discussed as well. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.099

文献信息

• High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation
  作者：Diána Marosvölgyi-Haskó、Attila Takács、Zsuzsanna Riedl、László Kollár

  DOI：10.1016/j.tet.2010.11.099

  日期：2011.2

  1-Isoindolinone derivatives were synthesised in high yields (up to 89%) by using 2-iodobenzyl bromide and 2-iodobenzylamine as bifunctional substrates in palladium-catalysed carbonylation. Depending on the N-nucleophiles, two types of compounds were synthesised with 2-iodobenzyl bromide: the use of primary amines, including amino acid methylesters, resulted in the formation of N-substituted 1-isoindolinones, while secondary amines react both with the benzyl bromide and iodoarene moieties resulting in the corresponding ortho-(N-piperidino/morpholinomethyl)-benzamides. The parent 1-isoindolinone was obtained in a facile, highly chemoselective intramolecular aminocarbonylation of 2-iodobenzylamine. The mechanistic details of the ring-closure reaction and the conditions leading to side-products are discussed as well. (C) 2010 Elsevier Ltd. All rights reserved.