ethyl (E)-4-(2-oxooxazolidin-3-yl)but-3-enoate | 1101366-40-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-4-(2-oxooxazolidin-3-yl)but-3-enoate
• 英文别名: ethyl (E)-4-(2-oxo-1,3-oxazolidin-3-yl)but-3-enoate
• CAS: 1101366-40-8
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: UXNFKDQIPVGPLT-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙烯基恶唑烷-2-酮 、 碘代醋酸乙酯 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 苯 为溶剂， 反应 22.0h， 以68%的产率得到ethyl (E)-4-(2-oxooxazolidin-3-yl)but-3-enoate
  参考文献：
  名称：

  Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

  摘要：

  A carbon-carbon bond construction method is disclosed which involves radical addition of alpha-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride was not observed. Rapid iodine atom transfer to (or electron transfer from) the radical adduct, resulting in an iminium ion intermediate and radical chain propagation, is consistent with the observed reactivity.

  DOI：

  10.1021/ol8028077

文献信息

• Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover
  作者：Gregory K. Friestad、Yaoping Wu

  DOI：10.1021/ol8028077

  日期：2009.2.19

  A carbon-carbon bond construction method is disclosed which involves radical addition of alpha-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride was not observed. Rapid iodine atom transfer to (or electron transfer from) the radical adduct, resulting in an iminium ion intermediate and radical chain propagation, is consistent with the observed reactivity.