(2S)-2-Bromo-N-((1'R)-phenylethyl)propanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-Bromo-N-((1'R)-phenylethyl)propanamide
• 英文别名: (2S)-2-bromo-N-[(1R)-1-phenylethyl]propanamide
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: QYAAFAXOBIYBIR-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  咪唑 、 (2S)-2-Bromo-N-((1'R)-phenylethyl)propanamide 在 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 45.0h， 以71%的产率得到(2R)-2-(1'-imidazolyl)-N-((1'R)-phenylethyl)propanamide
  参考文献：
  名称：

  Stereoselective synthesis of neutral and cationic 2-heterocyclically substituted propanamides

  摘要：

  Neutral (2R)-2-(1'-imidazolyl)-N-[(1'R)-phenylethyl]propanamide 5 and the related methylimidazolium and pyridinium salts 6-9 were easily prepared from 2-bromoamide la and imidazole, N-methylimidazole and pyridine at room temperature in toluene. The stereoselectivity was lower than with other nucleophiles, Ag+ and Ag2O proving less selective promoters, and Ag2O allowing racemization of starting material and side reactions to be observed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00527-2

文献信息

• Stereoselective Substitution in 2-Bromo Amides in the Presence of Ag+ or Ag2O
  作者：Ferruccio D'Angeli、Paolo Marchetti、Valerio Bertolasi

  DOI：10.1021/jo00118a017

  日期：1995.6

  Bromine displacement by a primary, secondary, or tertiary amine, or methanol, in chiral nonracemic (S)-2-bromopropanamides 1 occurs with high yields and stereo selectivity. Soluble Ag+ promotes inversion, and solid Ag2O promotes retention of configuration. However, in the case of Et(3)N, Ag+ promotes retention. With the hindered 2-bromo-2-methylbutanamide 5, the displacement by a primary or secondary amine or methanol occurs only in the presence of Ag2O, possibly with retention of configuration.
• Stereoselective synthesis of neutral and cationic 2-heterocyclically substituted propanamides
  作者：Paolo Marchetti、Ferruccio D'Angeli、Valerio Bertolasi

  DOI：10.1016/s0957-4166(97)00527-2

  日期：1997.11

  Neutral (2R)-2-(1'-imidazolyl)-N-[(1'R)-phenylethyl]propanamide 5 and the related methylimidazolium and pyridinium salts 6-9 were easily prepared from 2-bromoamide la and imidazole, N-methylimidazole and pyridine at room temperature in toluene. The stereoselectivity was lower than with other nucleophiles, Ag+ and Ag2O proving less selective promoters, and Ag2O allowing racemization of starting material and side reactions to be observed. (C) 1997 Elsevier Science Ltd.