(R)-N-(2-oxo-2-phenylethanoyl)-5-methyl-2-oxopyrrolidine | 158953-24-3

• 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: (R)-N-(2-oxo-2-phenylethanoyl)-5-methyl-2-oxopyrrolidine
• 英文别名: (R)-5-methyl-2-pyrrolidinone phenylglyoxylate；1-[(2R)-2-methyl-5-oxopyrrolidin-1-yl]-2-phenylethane-1,2-dione
• CAS: 158953-24-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: IVSTVMNAQHEPND-SECBINFHSA-N

物化性质

• 沸点：
  361.1±25.0 °C(predicted)
• 密度：
  1.237±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-(2-oxo-2-phenylethanoyl)-5-methyl-2-oxopyrrolidine 在 三甲基乙酸 作用下， 以 乙腈 为溶剂， 生成 (5R,2'R)-N-(2-hydroxy-2-phenylethanoyl)-5-methyl-2-oxopyrrolidine 、 (5R,2'S)-N-(2-hydroxy-2-phenylethanoyl)-5-methyl-2-oxopyrrolidine
  参考文献：
  名称：

  Diastereoselective cathodic reduction of chiral phenylglyoxylamides

  摘要：

  The cathodic reduction of (R)-5-methyl-2-pyrrolidinone- and (S)-4-isopropyl-2-oxazolidinone phenylglyoxylate affords the corresponding mandelic acid derivatives in 82-90% chemical yield and 42-81% de depending on electrolyte and temperature.

  DOI：

  10.1016/s0040-4039(00)77263-7
• 作为产物：
  描述：

  苯甲酰甲酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (R)-N-(2-oxo-2-phenylethanoyl)-5-methyl-2-oxopyrrolidine
  参考文献：
  名称：

  Electro-organic Synthesis 68. Diastereoselective Cathodic Reduction of Phenylglyoxylic Acid Attached to Chiral Auxiliaries.

  摘要：

  Two chiral auxiliaries were attached to phenylglyoxylic acid as amides in 67-70% yield. Cyclic voltammetry of one amide in acetonitrile-pivalic acid (0.117 mol l(-1)) shows that it is irreversibly reduced at --0.73 to -1.07 V (vs. Ag/AgCl) depending on the cation of the supporting electrolyte. During preparative-scale electrolysis the amides afforded the corresponding mandelic acid derivatives in 64-76% yield and 52-86% de, respectively. The diastereoselectivities depend on solvent, proton donor, supporting electrolyte, temperature and the substituent R in the 2-oxo acid amides. The results are in accordance with an ECE-reduction of the Zero acid amide to an enolate anion, which subsequently undergoes a face-selective protonation to the mandelic acid amide.

  DOI：

  10.3891/acta.chem.scand.53-1023

文献信息

• Diastereoselective cathodic reduction of chiral phenylglyoxylamides
  作者：Claudia Zielinski、Hans J. Schäfer

  DOI：10.1016/s0040-4039(00)77263-7

  日期：1994.8

  The cathodic reduction of (R)-5-methyl-2-pyrrolidinone- and (S)-4-isopropyl-2-oxazolidinone phenylglyoxylate affords the corresponding mandelic acid derivatives in 82-90% chemical yield and 42-81% de depending on electrolyte and temperature.
• Electro-organic Synthesis 68. Diastereoselective Cathodic Reduction of Phenylglyoxylic Acid Attached to Chiral Auxiliaries.
  作者：Christian Reufer、Claudia Zielinski、Hans Jürgen Schäfer、Roland Frölich、Alfred Sillesen、O. Mønsted、J. C. Rasmussen、H. Toftlund

  DOI：10.3891/acta.chem.scand.53-1023

  日期：——

  Two chiral auxiliaries were attached to phenylglyoxylic acid as amides in 67-70% yield. Cyclic voltammetry of one amide in acetonitrile-pivalic acid (0.117 mol l(-1)) shows that it is irreversibly reduced at --0.73 to -1.07 V (vs. Ag/AgCl) depending on the cation of the supporting electrolyte. During preparative-scale electrolysis the amides afforded the corresponding mandelic acid derivatives in 64-76% yield and 52-86% de, respectively. The diastereoselectivities depend on solvent, proton donor, supporting electrolyte, temperature and the substituent R in the 2-oxo acid amides. The results are in accordance with an ECE-reduction of the Zero acid amide to an enolate anion, which subsequently undergoes a face-selective protonation to the mandelic acid amide.