(2S)-2-bromopropanenitrile | 50529-79-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-2-bromopropanenitrile
• 英文别名: (S)-2-bromopropionitrile；L(-)-2-bromo-propionitrile；L(-)-2-Brom-propionitril；Propanenitrile, 2-bromo-, (S)-
• CAS: 50529-79-8
• 化学式: C₃H₄BrN
• 分子量: 133.975
• InChiKey: PYNYHMRMZOGVML-VKHMYHEASA-N

物化性质

• 沸点：
  144.8±0.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-2-bromopropanenitrile 、 1-(2,5-二氟苯基)-2-(1H-1,2,4-三唑-1-基)乙酮 艾沙康唑中间体 在 indium 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 以89.5%的产率得到3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl) butyronitrile
  参考文献：
  名称：

  一种制造艾沙康唑或雷夫康唑的方法

  摘要：

  本发明为用于制造非对映异构体以及对映异构体富集的三氮唑化合物艾沙康唑或雷夫康唑的方法，该方法包括酮与2-卤代金属丙腈之间进行雷福尔马茨基反应，生成对映异构体混合物随后进行拆分的步骤。本发明的方法明显减少了合成艾沙康唑和雷夫康唑的步骤，提高产物收率，降低生产成本。

  公开号：

  CN106317044A
• 作为产物：
  描述：

  (2S)-2-bromopropanamide 在 phosphorus pentoxide 作用下， 生成 (2S)-2-bromopropanenitrile
  参考文献：
  名称：

  Optically Active α-Bromopropionitrile

  摘要：

  DOI：

  10.1021/ja01855a048
• 作为试剂：
  描述：

  N-二甲氨基苄叔丁胺 在 (2S)-2-bromopropanenitrile 、 双氧水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 2-tert.-Butyl-3-phenyl-oxaziridin 、 2-tert-butyl-3-phenyl-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

• Optically Active α-Bromopropionitrile
  作者：Kenneth L. Berry、Julian M. Sturtevant

  DOI：10.1021/ja01855a048

  日期：1941.10
• 一种制造艾沙康唑或雷夫康唑的方法
  申请人：刘玫君

  公开号：CN106317044A

  公开（公告）日：2017-01-11

  本发明为用于制造非对映异构体以及对映异构体富集的三氮唑化合物艾沙康唑或雷夫康唑的方法，该方法包括酮与2-卤代金属丙腈之间进行雷福尔马茨基反应，生成对映异构体混合物随后进行拆分的步骤。本发明的方法明显减少了合成艾沙康唑和雷夫康唑的步骤，提高产物收率，降低生产成本。
• 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.