2-((4S,5R)-2-Oxo-4,5-diphenyl-oxazolidin-3-yl)-acrylic acid benzyl ester | 161633-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-((4S,5R)-2-Oxo-4,5-diphenyl-oxazolidin-3-yl)-acrylic acid benzyl ester
• 英文别名: benzyl 2-[(4S,5R)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]prop-2-enoate
• CAS: 161633-84-7
• 化学式: C₂₅H₂₁NO₄
• 分子量: 399.446
• InChiKey: UKLGRONHLYMSPG-XZOQPEGZSA-N

物化性质

• 沸点：
  538.6±60.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异丙基氯化镁 、 2-((4S,5R)-2-Oxo-4,5-diphenyl-oxazolidin-3-yl)-acrylic acid benzyl ester 在 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Asymmetric Synthesis of .alpha.-Amino Acids by Copper-Catalyzed Conjugate Addition of Grignard Reagents to Optically Active Carbamatoacrylates

  摘要：

  Optically active ene carbamates were alpha-lithiated by lithium tetramethylpiperidide in the presence of trialkylstannyl chlorides to produce alpha-stannylated compounds. These underwent facile palladium-catalyzed couplings with acid chlorides to produce alpha-keto ene carbamates in good yield. Treatment of the alpha-stannyl ene carbamates with butyllithium followed by quenching with carbon dioxide and esterification gave optically active carbamatoacrylates. Copper-catalyzed addition of tert-butyl-, 1-naphthyl-, 2-propenyl-, p-methoxyphenyl-, (trimethylsilyl)methyl-, cyclohexyl-, 1-adamantyl-, and isopropyl Grigard reagents followed by quenching at -10 to 25 degrees C and removal of the protecting groups gave the corresponding alpha-amino acids in 70-90% yield and 73-97% ee. Quenching the reaction at low temperature resulted in little if any asymmetric induction.

  DOI：

  10.1021/ja00097a020
• 作为产物：
  描述：

  (4S,5R)-4,5-Diphenyl-3-(1-trimethylstannanyl-vinyl)-oxazolidin-2-one 在 正丁基锂 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2-((4S,5R)-2-Oxo-4,5-diphenyl-oxazolidin-3-yl)-acrylic acid benzyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of .alpha.-Amino Acids by Copper-Catalyzed Conjugate Addition of Grignard Reagents to Optically Active Carbamatoacrylates

  摘要：

  Optically active ene carbamates were alpha-lithiated by lithium tetramethylpiperidide in the presence of trialkylstannyl chlorides to produce alpha-stannylated compounds. These underwent facile palladium-catalyzed couplings with acid chlorides to produce alpha-keto ene carbamates in good yield. Treatment of the alpha-stannyl ene carbamates with butyllithium followed by quenching with carbon dioxide and esterification gave optically active carbamatoacrylates. Copper-catalyzed addition of tert-butyl-, 1-naphthyl-, 2-propenyl-, p-methoxyphenyl-, (trimethylsilyl)methyl-, cyclohexyl-, 1-adamantyl-, and isopropyl Grigard reagents followed by quenching at -10 to 25 degrees C and removal of the protecting groups gave the corresponding alpha-amino acids in 70-90% yield and 73-97% ee. Quenching the reaction at low temperature resulted in little if any asymmetric induction.

  DOI：

  10.1021/ja00097a020