(S)-4-isopropyl-2-oxo-N-[2-(2-furyl)-2-oxoethanoyl]-1,3-oxazolidine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-isopropyl-2-oxo-N-[2-(2-furyl)-2-oxoethanoyl]-1,3-oxazolidine
• 英文别名: 1-(furan-2-yl)-2-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]ethane-1,2-dione
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: XWAOAHRLKZZURY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-2-oxo-N-[2-(2-furyl)-2-oxoethanoyl]-1,3-oxazolidine 在 lithium tetrafluoroborate 、 三甲基乙酸 作用下， 以 乙腈 为溶剂， 生成 (4S,2'R)-N-[2-hydroxy-2-(2-furyl)ethanoyl]-4-isopropyl-2-oxo-1,3-oxazolidine 、 (4S,2'S)-N-[2-hydroxy-2-(2-furyl)ethanoyl]-4-isopropyl-2-oxo-1,3-oxazolidine
  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
• 作为产物：
  描述：

  α-氧代-2-呋喃乙酸 在 正丁基锂 、 草酰氯 、 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 1.0h， 生成 (S)-4-isopropyl-2-oxo-N-[2-(2-furyl)-2-oxoethanoyl]-1,3-oxazolidine
  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

• 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.