(E)-4-methoxybenzyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate | 1197006-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4-methoxybenzyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate
• CAS: 1197006-45-3
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: PVIMZYOZHAKSRG-IENJSVCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-4-methoxybenzyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate 、 N-(4-nitrobenzyl)benzimidoyl chloride 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到(2'S,2R,3S,4S)-{[3,4-dihydro-4-(4-methoxybenzyl)-2-(4-nitrophenyl)-5-phenyl-2H-pyrrol-3-yl]-carbonyl}-2-oxo-4-phenyloxazolidine
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584
• 作为产物：
  描述：

  (S)-4-苯基-2-恶唑烷酮 、 (E)-3-[(4-methoxyphenyl)methoxy]prop-2-enoyl chloride 在 甲基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (E)-4-methoxybenzyl 4-oxo-4-((S)-2-oxo-4-phenyloxazolidin-3-yl)but-2-enoate
  参考文献：
  名称：

  Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

  摘要：

  Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity In the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.

  DOI：

  10.1021/ol9018584