2-(N-morpholylmethyl)-N,N-(3-oxapentane-1,5-diyl)benzamide | 1268618-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(N-morpholylmethyl)-N,N-(3-oxapentane-1,5-diyl)benzamide
• 英文别名: Morpholin-4-yl-[2-(morpholin-4-ylmethyl)phenyl]methanone；morpholin-4-yl-[2-(morpholin-4-ylmethyl)phenyl]methanone
• CAS: 1268618-99-0
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: LFPAIFDCZZWXOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吗啉 、 一氧化碳 、 2-碘苯甲基溴 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 ℃ 、100.0 kPa 条件下， 反应 24.0h， 以72%的产率得到2-(N-morpholylmethyl)-N,N-(3-oxapentane-1,5-diyl)benzamide
  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