(1S,5R,6S,7R)-6-methyltricyclo[5.4.0.01,5]undecan-11-one | 126434-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R,6S,7R)-6-methyltricyclo[5.4.0.01,5]undecan-11-one
• CAS: 126434-11-5；126434-13-7；148346-73-0；148346-74-1
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: SXAWRQQDIGERKH-DNRKLUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  己-4-炔-1-醇 在 Lindlar's catalyst 盐酸 、 正丁基锂 、 氢气 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， -78.0~50.0 ℃ 、101.33 kPa 条件下， 反应 14.83h， 生成 (1S,5R,6S,7R)-6-methyltricyclo[5.4.0.01,5]undecan-11-one
  参考文献：
  名称：

  Regiochemistry and stereochemistry of intramolecular [2+2] photocycloaddition of carbon-carbon double bonds to cyclohexenones

  摘要：

  The intramolecular [2 + 2] photocycloaddition mechanism of alkenes tethered by a three-methylene chain to cyclohexenones has been studied. It was found that the reversion from a 1,4-diradical intermediate to starting material is slow relative to the rate of photoadduct formation. Only ''straight'' closure was observed in the systems studied. For compounds 1-3 and 5, the assumption that the first bond is formed between the beta-carbon of the enone and C-4' leading to a 1,4-diradical is supported. For the formation of compounds 6-11, possible mechanisms are discussed.

  DOI：

  10.1021/jo00014a040