(Z)-3-amino-6-chloro-1-(cyclohexen-1-yl)hept-2-en-1-one | 141346-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-amino-6-chloro-1-(cyclohexen-1-yl)hept-2-en-1-one
• CAS: 141346-22-7
• 化学式: C₁₃H₂₀ClNO
• 分子量: 241.761
• InChiKey: AXEMOQXUMAKNAP-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  7-methylenebicyclo[4.1.0]heptane 在 potassium carbonate 、 异氰酸苯酯 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.5h， 生成 (Z)-3-amino-6-chloro-1-(cyclohexen-1-yl)hept-2-en-1-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

文献信息

• 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
  作者：Ernesto G. Occhiato、Antonio Guarna、Alberto Brandi、Andrea Goti、Francesco De Sarlo

  DOI：10.1021/jo00041a027

  日期：1992.7

  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.