(3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate | 750649-46-8

• 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: (3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate
• 英文别名: [(3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl] (3R)-3-(4-chlorophenyl)-4-nitrobutanoate
• CAS: 750649-46-8
• 化学式: C₂₂H₂₃ClN₂O₅
• 分子量: 430.888
• InChiKey: MOZPGIIFHJGSDF-JXFKEZNVSA-N

物化性质

• 沸点：
  626.3±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate 在 镍 lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 49.0h， 生成 R(+)-巴氯芬盐酸盐
  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：

  对氯肉桂酸 在 4-二甲氨基吡啶 、 苄基三乙基氯化铵 、 N,N'-二环己基碳二亚胺 、 cesium fluoride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 76.0h， 生成 (3R,3'R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl 4-nitro-3-(4-chlorophenyl)butanoate
  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

文献信息

• Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries
  作者：Pelayo Camps、Diego Muñoz-Torrero、Laura Sánchez

  DOI：10.1016/j.tetasy.2004.05.021

  日期：2004.7

  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.