(R)-2-chlorobutyric acid methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-chlorobutyric acid methyl ester
• 英文别名: methyl (R)-2-chlorobutanoate；methyl (2R)-2-chlorobutanoate
• 化学式: C₅H₉ClO₂
• 分子量: 136.578
• InChiKey: BHQQXAOBIZQEGI-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-chlorobutyric acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以90 %的产率得到(R)-2-氯丁酸
  参考文献：
  名称：

  CN116332785

  摘要：

  公开号：
• 作为产物：
  描述：

  (Z)2-氯-2-丁烯酸甲酯 在 葡萄糖 、 enoate reductase old yellow enzyme 2 from S_. cerevisiae 、 GDH from B_. megaterium 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl (S)-2-chlorobutanoate 、 (R)-2-chlorobutyric acid methyl ester
  参考文献：
  名称：

  Enoate Reductase-Mediated Preparation of Methyl (S)-2-Bromobutanoate, a Useful Key Intermediate for the Synthesis of Chiral Active Pharmaceutical Ingredients

  摘要：

  Enoate reductases belonging to the Old Yellow Enzyme (OYE) family were employed to develop a biocatalysed approach to methyl (S)-2-bromobutanoate, a key intermediate for the introduction of a particular stereogenic unit into the molecular skeleton of a certain class of chiral drugs. Methyl (Z)-2-bromocrotonate afforded, respectively, (S)-2-bromobutanoic acid (ee = 97%) and methyl (S)-2-bromobutanoate (ee = 97%) by baker's yeast fermentation and by OYE1-3 biotransformations. The bioreductions of other methyl 2-haloalkenoates were also considered. It was observed that the (Z)- and (E)-diastereoisomers of alpha-bromo unsaturated esters afforded the same enantiomer of the corresponding reduced product.

  DOI：

  10.1021/op200086t

文献信息

• Enoate Reductase-Mediated Preparation of Methyl (<i>S</i>)-2-Bromobutanoate, a Useful Key Intermediate for the Synthesis of Chiral Active Pharmaceutical Ingredients
  作者：Elisabetta Brenna、Francesco G. Gatti、Alessia Manfredi、Daniela Monti、Fabio Parmeggiani

  DOI：10.1021/op200086t

  日期：2012.2.17

  Enoate reductases belonging to the Old Yellow Enzyme (OYE) family were employed to develop a biocatalysed approach to methyl (S)-2-bromobutanoate, a key intermediate for the introduction of a particular stereogenic unit into the molecular skeleton of a certain class of chiral drugs. Methyl (Z)-2-bromocrotonate afforded, respectively, (S)-2-bromobutanoic acid (ee = 97%) and methyl (S)-2-bromobutanoate (ee = 97%) by baker's yeast fermentation and by OYE1-3 biotransformations. The bioreductions of other methyl 2-haloalkenoates were also considered. It was observed that the (Z)- and (E)-diastereoisomers of alpha-bromo unsaturated esters afforded the same enantiomer of the corresponding reduced product.
• CN116332785
  申请人：——

  公开号：——

  公开（公告）日：——