(S)-ethyl 2-methyl-3-oxo-2-(2-(2,2,2-trifluoroacetamido)phenyl)butanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-ethyl 2-methyl-3-oxo-2-(2-(2,2,2-trifluoroacetamido)phenyl)butanoate
• 英文别名: ethyl (2S)-2-methyl-3-oxo-2-[2-[(2,2,2-trifluoroacetyl)amino]phenyl]butanoate
• 化学式: C₁₅H₁₆F₃NO₄
• 分子量: 331.292
• InChiKey: BGNIKCJKCISGKI-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 、 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 在 sodium hydroxide 、 copper(l) iodide 、 4-hydroxyproline 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (R)-ethyl 2-methyl-3-oxo-2-(2-(2,2,2-trifluoroacetamido)phenyl)butanoate 、 (S)-ethyl 2-methyl-3-oxo-2-(2-(2,2,2-trifluoroacetamido)phenyl)butanoate
  参考文献：
  名称：

  Enantioselective Arylation of 2-Methylacetoacetates Catalyzed by CuI/trans-4-Hydroxy-l-proline at Low Reaction Temperatures

  摘要：

  CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at -45 degrees C to create alpha-aryl all-carbon quaternary centers enantioselectively. Up to 93% ee was achieved when tert-butyl ester was used. The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.

  DOI：

  10.1021/ja066991j

文献信息

• Enantioselective Arylation of 2-Methylacetoacetates Catalyzed by CuI/<i>trans</i>-4-Hydroxy-<scp>l</scp>-proline at Low Reaction Temperatures
  作者：Xiaoan Xie、Yu Chen、Dawei Ma

  DOI：10.1021/ja066991j

  日期：2006.12.1

  CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at -45 degrees C to create alpha-aryl all-carbon quaternary centers enantioselectively. Up to 93% ee was achieved when tert-butyl ester was used. The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.