(E)-1-[5-Methyl-pyrrolidin-(2Z)-ylidene]-4-phenyl-but-3-en-2-one | 141346-27-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-[5-Methyl-pyrrolidin-(2Z)-ylidene]-4-phenyl-but-3-en-2-one
• 英文别名: (E,1Z)-1-(5-methylpyrrolidin-2-ylidene)-4-phenylbut-3-en-2-one
• CAS: 141346-27-2
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: MELYEQAOLHSBRE-LTBWBYIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-(3-Chlorobutyl)-1-phenyl-4-oxa-5-azaspiro<2.4>hept-5-ene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以26%的产率得到(3S,5R)-3-Methyl-5-phenyl-2,3,5,6-tetrahydro-1H-indolizin-7-one
  参考文献：
  名称：

  N-Bridgehead polycyclic compounds by sequential rearrangement-annulation of isoxazoline-5-spirocyclopropanes. 6. A general synthetic method for 5,6-dihydro-7(8H)- and 2,3,5,6-tetrahydro-7(1H)-indolizinones

  摘要：

  The thermal rearrangement-annulation of isoxazoline-5-spirocyclopropanes 4a-e substituted with a chain bearing a carbonyl group affords, in one step, 5,6-dihydro-7(8H)-indolizinones 5a-e. The rearrangement-annulation of isoxazoline-5-spirocyclopropanes 4f-h substituted with a chlorine on the side chain affords, also in one step, 2,3,5,6-tetrahydro-7(1H)-indolizinones 5f-h. When the cyclopropane ring is fused to a cyclohexane, or when a cyclohexanone is present in the side chain of isoxazoline 4, the process leads to N-bridgehead tricyclic compounds. Short rection times, mild reaction conditions, complete regioselectivity, and good stereoselectivity are the valuable features of this strategy.

  DOI：

  10.1021/jo00041a027