(3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-(4-isobutylphenyl)propionate | 674776-35-3

• 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)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-(4-isobutylphenyl)propionate
• 英文别名: [(3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl] (2R)-3-cyano-2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 674776-35-3
• 化学式: C₂₆H₃₀N₂O₃
• 分子量: 418.536
• InChiKey: FKYCPOGQZMVJLW-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-(4-isobutylphenyl)propionate 在 palladium on activated charcoal lithium hydroxide 、 sodium hydroxide 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 生成 (R)-4-(tert-butoxycarbonylamino)-2-(4-isobutylphenyl)butanoic acid
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

  摘要：

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.035
• 作为产物：
  描述：

  异丁芬酸甲酯 在 sodium hydroxide 、 正丁基锂 、 3 A molecular sieve 、 五氯化磷 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 (3R)-4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl (2R)-3-cyano-2-(4-isobutylphenyl)propionate
  参考文献：
  名称：

  Stereoselective synthesis of both enantiomers of N-Boc-α-aryl-γ-aminobutyric acids

  摘要：

  Esterification of racemic alpha-aryl-beta-cyanopropionic acid chlorides with either (R)- or (S)-N-phenylpantolactam as the chiral auxiliary in the presence of Et3N resulted in the predominant formation of (alphaR,3'R)- or (alphaS,3'S)-configured pantolactam cyano ester, respectively, in nearly quantitative yields with diastereomeric ratios of up to 93:7. Column chromatography of the diastereoenriched cyano esters, followed by hydrolysis of the resulting diastereopure cyano esters under essentially nonracemizing conditions gave enantiopure alpha-aryl-beta-cyanopropionic acids, which were readily converted in high yields into enantiopure (OER)- and (alphaS)-configured N-tert-butoxycarbonyl-alpha-aryl-gamma-aminobutyric acid (GABA) derivatives of potential biological interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.035