(2RS,4SR)-4-cyano-2-methyl-3-oxo-2,4-diphenylbutyric acid methyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2RS,4SR)-4-cyano-2-methyl-3-oxo-2,4-diphenylbutyric acid methyl ester
• 英文别名: methyl (2R,4S)-4-cyano-2-methyl-3-oxo-2,4-diphenylbutanoate
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: XMBUJQVVGXUGMW-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,4SR)-4-cyano-2-methyl-3-oxo-2,4-diphenylbutyric acid methyl ester 反应 4.0h， 生成 (2RS,3RS)-3-cyano-2-methyl-2,3-diphenylpropionic acid methyl ester
  参考文献：
  名称：

  Enantiospecific Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers by Combination of Configurationally-Trapped Radical Pairs in Crystalline Solids

  摘要：

  [GRAPHIC]Photochemical irradiation of crystalline (2R,4S)-2-carbomethoxy-4-cyano-2,4-diphenyl-3-butanone 1 led to highly efficient decarbonylation reactions. Experiments with optically pure and racemic crystals showed that the intermediate radical pairs undergo a highly diastereo- and enantiospecific radical-radical combination that leads to the formation of two adjacent stereogenic centers in good chemical yield and with high chemical control. Reactions with chiral crystals occurred with quantitative enantiomeric yields and >95% diastereomeric yields.

  DOI：

  10.1021/ol0347803
• 作为产物：
  描述：

  2-苯基丙酸 在 正丁基锂 、 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2RS,4SR)-4-cyano-2-methyl-3-oxo-2,4-diphenylbutyric acid methyl ester
  参考文献：
  名称：

  Enantiospecific Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers by Combination of Configurationally-Trapped Radical Pairs in Crystalline Solids

  摘要：

  [GRAPHIC]Photochemical irradiation of crystalline (2R,4S)-2-carbomethoxy-4-cyano-2,4-diphenyl-3-butanone 1 led to highly efficient decarbonylation reactions. Experiments with optically pure and racemic crystals showed that the intermediate radical pairs undergo a highly diastereo- and enantiospecific radical-radical combination that leads to the formation of two adjacent stereogenic centers in good chemical yield and with high chemical control. Reactions with chiral crystals occurred with quantitative enantiomeric yields and >95% diastereomeric yields.

  DOI：

  10.1021/ol0347803

文献信息

• Enantiospecific Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers by Combination of Configurationally-Trapped Radical Pairs in Crystalline Solids
  作者：Martha E. Ellison、Danny Ng、Hung Dang、Miguel A. Garcia-Garibay

  DOI：10.1021/ol0347803

  日期：2003.7.1

  [GRAPHIC]Photochemical irradiation of crystalline (2R,4S)-2-carbomethoxy-4-cyano-2,4-diphenyl-3-butanone 1 led to highly efficient decarbonylation reactions. Experiments with optically pure and racemic crystals showed that the intermediate radical pairs undergo a highly diastereo- and enantiospecific radical-radical combination that leads to the formation of two adjacent stereogenic centers in good chemical yield and with high chemical control. Reactions with chiral crystals occurred with quantitative enantiomeric yields and >95% diastereomeric yields.