5-methyl-4-methylenebicyclo<3.3.0>oct-1-en-3-one | 74320-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-4-methylenebicyclo<3.3.0>oct-1-en-3-one
• 英文别名: 6a-methyl-1-methylidene-5,6-dihydro-4H-pentalen-2-one
• CAS: 74320-67-5
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: BUOWDTQBOPPPGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-庚炔-2-酮 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.17h， 生成 5-methyl-4-methylenebicyclo<3.3.0>oct-1-en-3-one
  参考文献：
  名称：

  Palladium-catalyzed intramolecular alkyne-carbon monoxide-alkene insertion cascade for synthesis of .alpha.-methylenecyclopentenones

  摘要：

  A method for the construction of alpha-methylenecyclopentenones fused to five-membered rings using a palladium catalyst is reported. The procedure involves the formation of pi-allylpalladium intermediates that undergo sequential intramolecular alkyne insertion, carbon monoxide insertion, intramolecular alkene insertion, and beta-hydride elimination. Examples of the cyclization are seen in eq 2 and Scheme III.

  DOI：

  10.1021/jo00055a006

文献信息

• Palladium-catalyzed intramolecular alkyne-carbon monoxide-alkene insertion cascade for synthesis of .alpha.-methylenecyclopentenones
  作者：Nathan C. Ihle、Clayton H. Heathcock

  DOI：10.1021/jo00055a006

  日期：1993.1

  A method for the construction of alpha-methylenecyclopentenones fused to five-membered rings using a palladium catalyst is reported. The procedure involves the formation of pi-allylpalladium intermediates that undergo sequential intramolecular alkyne insertion, carbon monoxide insertion, intramolecular alkene insertion, and beta-hydride elimination. Examples of the cyclization are seen in eq 2 and Scheme III.