6-(3-Oxobutyl)-1-phenyl-4-oxa-5-azaspiro<2.4>hept-5-ene | 141346-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3-Oxobutyl)-1-phenyl-4-oxa-5-azaspiro<2.4>hept-5-ene
• 英文别名: 4-(2-Phenyl-4-oxa-5-azaspiro[2.4]hept-5-en-6-yl)butan-2-one
• CAS: 141346-00-1
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: CBWCLRNKBPVDME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(3-Oxobutyl)-1-phenyl-4-oxa-5-azaspiro<2.4>hept-5-ene 以 均三甲苯 为溶剂， 反应 0.5h， 以64%的产率得到3-Methyl-5-phenyl-5,6-dihydro-7(8H)-indolizinone
  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
• 作为产物：
  描述：

  5-硝基-2-戊酮 、 1-methylene-2-phenylcyclopropane 在 异氰酸苯酯 、 三乙胺 作用下， 以 乙醚 为溶剂， 以0.3%的产率得到4-(2-phenyl-5-oxa-6-azaspiro[2.4]hept-6-en-7-yl)butan-2-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.

表征谱图