(R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester | 212568-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester
• CAS: 212568-27-9
• 化学式: C₁₅H₁₈ClNO₃
• 分子量: 295.766
• InChiKey: SMSGUSKSHFQMQJ-ZYHUDNBSSA-N

物化性质

• 沸点：
  447.5±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以85%的产率得到(R)-2-chloropropionic acid
  参考文献：
  名称：

  (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-aryloxypropanoic acid herbicides and α-chlorocarboxylic acids

  摘要：

  rac-alpha-Chlorocarboxylic acids, rac-9a-e, were formally deracemized by reaction of the corresponding acyl chlorides with the chiral auxiliaries (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, (R)- and (S)-4, followed by mild alkaline hydrolysis. The highest o.p. (99%) was obtained in the case of (S)-alpha-chloropropanoic acid, a known precursor for the synthesis of (R)-alpha-aryloxypropanoic acid herbicides such as dichlorprop-P, (R)-3a, or mecoprop-P, (R)-3b, which, together with their enantiomers, were also obtained in moderate e.e.s by dynamic kinetic resolution from (alpha RS, 3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl alpha-bromopropanoate, (alpha RS, 3S)-6, by reaction with the corresponding phenoxide followed by mild acid hydrolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00194-3
• 作为产物：
  描述：

  2-氯丙酰氯 、 2-吡咯烷酮,3-羟基-4,4-二甲基-1-苯基-,(3S)- 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以69%的产率得到(R)-2-Chloro-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester
  参考文献：
  名称：

  (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-aryloxypropanoic acid herbicides and α-chlorocarboxylic acids

  摘要：

  rac-alpha-Chlorocarboxylic acids, rac-9a-e, were formally deracemized by reaction of the corresponding acyl chlorides with the chiral auxiliaries (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone, (R)- and (S)-4, followed by mild alkaline hydrolysis. The highest o.p. (99%) was obtained in the case of (S)-alpha-chloropropanoic acid, a known precursor for the synthesis of (R)-alpha-aryloxypropanoic acid herbicides such as dichlorprop-P, (R)-3a, or mecoprop-P, (R)-3b, which, together with their enantiomers, were also obtained in moderate e.e.s by dynamic kinetic resolution from (alpha RS, 3S)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl alpha-bromopropanoate, (alpha RS, 3S)-6, by reaction with the corresponding phenoxide followed by mild acid hydrolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00194-3