2-Methyl-5-cyclohexylhex-4-en-6-olide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-Methyl-5-cyclohexylhex-4-en-6-olide
• 英文别名: 6-cyclohexyl-3-methyl-4,7-dihydro-2(3H)-oxepinone；3-cyclohexyl-6-methyl-5,6-dihydro-2H-oxepin-7-one
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: YMUBQZVVZCFWMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酰基环己烷 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丁酮 为溶剂， 反应 25.92h， 生成 2-Methyl-5-cyclohexylhex-4-en-6-olide
  参考文献：
  名称：

  A Chelation-Controlled Ester Enolate Claisen Rearrangement

  摘要：

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.

  DOI：

  10.1021/jo00121a029

文献信息

• A ligand assisted Claisen rearrangement
  作者：Marie E. Krafft、Sandra Jarrett、Olivier A. Dasse

  DOI：10.1016/s0040-4039(00)61392-8

  日期：1993.12

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes via heteroatom mediated substrate pre-organization prior to rearrangement.
• A Chelation-Controlled Ester Enolate Claisen Rearrangement
  作者：Marie E. Krafft、Olivier A. Dasse、Sandra Jarrett、Anne Fievre

  DOI：10.1021/jo00121a029

  日期：1995.8

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.