(E)-3-(7-hydroxy-3-methyloct-1-enyl)oxazolidin-2-one | 1173276-70-4

• 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: (E)-3-(7-hydroxy-3-methyloct-1-enyl)oxazolidin-2-one
• CAS: 1173276-70-4
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: UFKVJHZUYSOLCU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(7-hydroxy-3-methyloct-1-enyl)oxazolidin-2-one 在 2,6-二氯吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 3-((E)-2-(2,6-dimethyltetrahydro-2H-pyran-2-yl)vinyl)oxazolidin-2-one 、 3-((E)-2-(2,6-dimethyltetrahydro-2H-pyran-2-yl)vinyl)oxazolidin-2-one
  参考文献：
  名称：

  Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

  摘要：

  Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

  DOI：

  10.1021/ol901188q
• 作为产物：
  描述：

  (E)-5-methyl-7-(2-oxooxazolidin-3-yl)hept-6-enal 、 甲基溴化镁 以 乙醚 为溶剂， 以70%的产率得到(E)-3-(7-hydroxy-3-methyloct-1-enyl)oxazolidin-2-one
  参考文献：
  名称：

  Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

  摘要：

  Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

  DOI：

  10.1021/ol901188q