(2S)-2-bromo-3-phenylpropanamide | 1415408-82-0

• 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-3-phenylpropanamide
• CAS: 1415408-82-0
• 化学式: C₉H₁₀BrNO
• 分子量: 228.088
• InChiKey: BJESFDVRFIKQGR-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 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：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-2-bromo-3-phenylpropanamide 在 氯化亚砜 作用下， 反应 2.0h， 以86%的产率得到(2S)-2-bromo-3-phenylpropanenitrile
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids

  摘要：

  Two methods were investigated for the preparation of six chiral alpha-bromonitriles with different optic purities. The nitrous deamination of amino acids gives alpha-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford alpha-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding alpha-bromoamids using thionyl chloride gives alpha-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

  DOI：

  10.1080/00397911.2011.608142
• 作为产物：
  描述：

  (2S)-2-bromo-3-phenylpropanoyl chloride 在 ammonium hydroxide 作用下， 以 水 为溶剂， 生成 (2S)-2-bromo-3-phenylpropanamide
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched α-Bromonitriles from Amino Acids

  摘要：

  Two methods were investigated for the preparation of six chiral alpha-bromonitriles with different optic purities. The nitrous deamination of amino acids gives alpha-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford alpha-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding alpha-bromoamids using thionyl chloride gives alpha-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.

  DOI：

  10.1080/00397911.2011.608142

文献信息

• Synthesis of Enantiomerically Enriched <font>α</font>-Bromonitriles from Amino Acids
  作者：Najeh Tka、Jamil Kraïem、Béchir Ben Hassine

  DOI：10.1080/00397911.2011.608142

  日期：2013.1.1

  Two methods were investigated for the preparation of six chiral alpha-bromonitriles with different optic purities. The nitrous deamination of amino acids gives alpha-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford alpha-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding alpha-bromoamids using thionyl chloride gives alpha-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.