(S)-2-(2-bromophenylamino)propionamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(2-bromophenylamino)propionamide
• 英文别名: (S)-N-(2-bromophenyl)alaninamide；(2S)-2-(2-bromoanilino)propanamide
• 化学式: C₉H₁₁BrN₂O
• 分子量: 243.103
• InChiKey: WWAUUHZVURYQLE-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-丙氨酰胺 、 邻碘溴苯 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以96%的产率得到
  参考文献：
  名称：

  Ligand-free CuI-catalyzed selective C–N coupling of aliphatic amino group of α-amino acid amides with ortho-dihaloarenes

  摘要：

  Many synthetic methods of racemic N-aryl (including N-(2-haloaryl)) alpha-amino acid amides have been reported, but there are only a few for eutomers and none for inactivated halo(hetero)arenes. Selective C-N coupling of aliphatic amino group of alpha-amino acid amides is a direct and valuable method, but still unresolved. Here we disclose a simple and cheap ligand-free CuI-catalyzed selective synthesis of chiral N-(2-halo(hetero)aryl) amino acid amides without obvious racemization. A rational mechanism is proposed. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.093

文献信息

• Ligand-free CuI-catalyzed selective C–N coupling of aliphatic amino group of α-amino acid amides with ortho-dihaloarenes
  作者：Yan Wang、Xingzhao Tu、Xirui Lv、Lihong Zhou、Qingle Zeng

  DOI：10.1016/j.tetlet.2013.08.093

  日期：2013.11

  Many synthetic methods of racemic N-aryl (including N-(2-haloaryl)) alpha-amino acid amides have been reported, but there are only a few for eutomers and none for inactivated halo(hetero)arenes. Selective C-N coupling of aliphatic amino group of alpha-amino acid amides is a direct and valuable method, but still unresolved. Here we disclose a simple and cheap ligand-free CuI-catalyzed selective synthesis of chiral N-(2-halo(hetero)aryl) amino acid amides without obvious racemization. A rational mechanism is proposed. (c) 2013 Elsevier Ltd. All rights reserved.