(R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-(4-chlorophenyl)-2-propenoate | 750649-50-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-(4-chlorophenyl)-2-propenoate
• 英文别名: [(3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl] (E)-3-(4-chlorophenyl)prop-2-enoate
• CAS: 750649-50-4
• 化学式: C₂₁H₂₀ClNO₃
• 分子量: 369.848
• InChiKey: NJQZSMYCLDDBEF-QHSLDKKCSA-N

物化性质

• 熔点：
  130-131 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  558.2±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-(4-chlorophenyl)-2-propenoate 在 nickel dichloride sodium tetrahydroborate 、 苄基三乙基氯化铵 、 cesium fluoride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 10.5h， 生成 (R)-巴氯芬内酰胺
  参考文献：
  名称：

  Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries

  摘要：

  Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3'R)- or (3S,3'S)-nitro esters with > 98:2 dr after column chromatography. Hydrolysis of the resulting diastereopure nitro esters gave the corresponding enantiopure nitro acids, which were readily converted in high yields into either (R)- or (S)-baclofen hydrochloride. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.021
• 作为产物：
  描述：

  (3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate 在 nickel dichloride 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 78.5h， 生成 (R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 3-(4-chlorophenyl)-2-propenoate
  参考文献：
  名称：

  Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries

  摘要：

  Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3'R)- or (3S,3'S)-nitro esters with > 98:2 dr after column chromatography. Hydrolysis of the resulting diastereopure nitro esters gave the corresponding enantiopure nitro acids, which were readily converted in high yields into either (R)- or (S)-baclofen hydrochloride. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.021