(2S,3S)-2-bromo-3-methylpentanenitrile | 1384954-10-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S)-2-bromo-3-methylpentanenitrile
• CAS: 1384954-10-2
• 化学式: C₆H₁₀BrN
• 分子量: 176.056
• InChiKey: WKQNVOHSURQKDO-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2S,3S)-2-bromo-3-methylpentanamide 在 氯化亚砜 作用下， 反应 2.0h， 以90%的产率得到(2S,3S)-2-bromo-3-methylpentanenitrile
  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
• 作为试剂：
  描述：

  (S)-N-(4-methoxybenzylidene)-α-methylbenzylamine 在 (2S,3S)-2-bromo-3-methylpentanenitrile 、 双氧水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(3R)-3-(4-methoxyphenyl)-2-[(1S)-1-phenylethyl]oxaziridine
  参考文献：
  名称：

  Enantio- and Diastereoselective Oxidation of N-Alkylimines Using Chiral α-Bromonitriles and Hydrogen Peroxide System

  摘要：

  Chiral alpha-bromonitriles were prepared with good chemical and optical yields starting from natural alpha-amino acids by dehydrating the corresponding alpha-bromoamides with thionyl chloride. The combined system alpha-bromonitriles/hydrogen peroxide was examined for the enantio- and diastereoselective oxidation of N-alkylimines in basic media at room temperature. The oxidation of N-tertiobutylarylimines leads to optically active oxaziridines with moderate enantiomeric excess. However, the oxidation of (S)-1-phenylethylarylimines affords the corresponding oxaziridines with good diasteromeric excess up to 97/3 as proved by gaseous-phase chromatography.

  DOI：

  10.1080/00397911.2011.573611

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.
• Enantio- and Diastereoselective Oxidation of <i>N</i>-Alkylimines Using Chiral <font>α</font>-Bromonitriles and Hydrogen Peroxide System
  作者：Najeh Tka、Jamil Kraïem、Béchir Ben Hassine

  DOI：10.1080/00397911.2011.573611

  日期：2012.10.15

  Chiral alpha-bromonitriles were prepared with good chemical and optical yields starting from natural alpha-amino acids by dehydrating the corresponding alpha-bromoamides with thionyl chloride. The combined system alpha-bromonitriles/hydrogen peroxide was examined for the enantio- and diastereoselective oxidation of N-alkylimines in basic media at room temperature. The oxidation of N-tertiobutylarylimines leads to optically active oxaziridines with moderate enantiomeric excess. However, the oxidation of (S)-1-phenylethylarylimines affords the corresponding oxaziridines with good diasteromeric excess up to 97/3 as proved by gaseous-phase chromatography.