ethyl (S)-2,2-difluoro-3-hydroxybutanoate | 1260148-25-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl (S)-2,2-difluoro-3-hydroxybutanoate
• 英文别名: ethyl (3S)-2,2-difluoro-3-hydroxybutanoate
• CAS: 1260148-25-1
• 化学式: C₆H₁₀F₂O₃
• 分子量: 168.14
• InChiKey: ONGVAFSENCMVGI-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 ethyl (S)-2,2-difluoro-3-hydroxybutanoate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.66h， 以65%的产率得到ethyl (S)-3-(trifluoromethanesulfonyloxy)-2,2-difluorobutanoate
  参考文献：
  名称：

  Chemoenzymatic synthesis of optically active alcohol and β-amino-acid derivative containing the difluoromethylene group

  摘要：

  The bioreduction of alpha,alpha-difluorinated ketones, ethyl 2,2-difluoro-3-oxobutanoate (2a) and 2,2-difluoro-1-phenyl-1,3-butanedione (2b), with cells of recombinant Escherichia coli overproducing SCR (Saccharomyces cerevisiae carbonyl reductase from bakers' yeast) and GDH (glucose dehydrogenase from Bacillus megaterium) gave enantiomerically pure alcohols, ethyl (S)-2,2-difluoro-3-hydroxybutanoate ((S)-1a) and (S)-2,2-difluoro-3-hydroxy-1-phenyl-1-butanone ((S)-1b), respectively, in the presence of NADP(+) and glucose in buffer. The reductions of 2a and 2b proceeded completely at the substrate concentrations of 0.4 M (67 g/L) and 1.0 M (200 g/L), respectively. The opposite enantiomers (R)-1a and (R)-1b were also produced by enzyme E039 (a mixture of carbonyl reductase and formate dehydrogenase) contained in Chiralscreen OH (Daicel Chemical Industries) in the presence of NADH and sodium formate in buffer. Enantiomerically pure (S)-1a was converted by organic synthetic methods into an a,a-difluorinated derivative of (R)-beta-aminobutyric acid (BABA) in three steps. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.05.009
• 作为产物：
  描述：

  2,2-二氟乙酰乙酸乙酯 在 葡萄糖 、 nicotinamide adenine dinucleotide phosphate 作用下， 反应 24.0h， 以61%的产率得到ethyl (S)-2,2-difluoro-3-hydroxybutanoate
  参考文献：
  名称：

  Chemoenzymatic synthesis of optically active alcohol and β-amino-acid derivative containing the difluoromethylene group

  摘要：

  The bioreduction of alpha,alpha-difluorinated ketones, ethyl 2,2-difluoro-3-oxobutanoate (2a) and 2,2-difluoro-1-phenyl-1,3-butanedione (2b), with cells of recombinant Escherichia coli overproducing SCR (Saccharomyces cerevisiae carbonyl reductase from bakers' yeast) and GDH (glucose dehydrogenase from Bacillus megaterium) gave enantiomerically pure alcohols, ethyl (S)-2,2-difluoro-3-hydroxybutanoate ((S)-1a) and (S)-2,2-difluoro-3-hydroxy-1-phenyl-1-butanone ((S)-1b), respectively, in the presence of NADP(+) and glucose in buffer. The reductions of 2a and 2b proceeded completely at the substrate concentrations of 0.4 M (67 g/L) and 1.0 M (200 g/L), respectively. The opposite enantiomers (R)-1a and (R)-1b were also produced by enzyme E039 (a mixture of carbonyl reductase and formate dehydrogenase) contained in Chiralscreen OH (Daicel Chemical Industries) in the presence of NADH and sodium formate in buffer. Enantiomerically pure (S)-1a was converted by organic synthetic methods into an a,a-difluorinated derivative of (R)-beta-aminobutyric acid (BABA) in three steps. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.05.009

文献信息

• Chemoenzymatic synthesis of optically active alcohol and β-amino-acid derivative containing the difluoromethylene group
  作者：Tadashi Ema、Taro Kadoya、Kumiko Akihara、Takashi Sakai

  DOI：10.1016/j.molcatb.2010.05.009

  日期：2010.9

  The bioreduction of alpha,alpha-difluorinated ketones, ethyl 2,2-difluoro-3-oxobutanoate (2a) and 2,2-difluoro-1-phenyl-1,3-butanedione (2b), with cells of recombinant Escherichia coli overproducing SCR (Saccharomyces cerevisiae carbonyl reductase from bakers' yeast) and GDH (glucose dehydrogenase from Bacillus megaterium) gave enantiomerically pure alcohols, ethyl (S)-2,2-difluoro-3-hydroxybutanoate ((S)-1a) and (S)-2,2-difluoro-3-hydroxy-1-phenyl-1-butanone ((S)-1b), respectively, in the presence of NADP(+) and glucose in buffer. The reductions of 2a and 2b proceeded completely at the substrate concentrations of 0.4 M (67 g/L) and 1.0 M (200 g/L), respectively. The opposite enantiomers (R)-1a and (R)-1b were also produced by enzyme E039 (a mixture of carbonyl reductase and formate dehydrogenase) contained in Chiralscreen OH (Daicel Chemical Industries) in the presence of NADH and sodium formate in buffer. Enantiomerically pure (S)-1a was converted by organic synthetic methods into an a,a-difluorinated derivative of (R)-beta-aminobutyric acid (BABA) in three steps. (C) 2010 Elsevier B.V. All rights reserved.