4-(3-pentynyl)-4-hydroxycyclohexa-2,5-dienone | 135614-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3-pentynyl)-4-hydroxycyclohexa-2,5-dienone
• 英文别名: 4-Hydroxy-4-pent-3-ynylcyclohexa-2,5-dien-1-one
• CAS: 135614-75-4
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: AZVLJEPNQKQLRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-pentynyl)-4-hydroxycyclohexa-2,5-dienone 在 三乙胺 、 mercury dichloride 作用下， 以 xylene 为溶剂， 反应 4.0h， 以35%的产率得到1-methylspiro<3.5>deca-6,9-diene-2,8-dione
  参考文献：
  名称：

  Spiro-fused 2,5-cyclohexadienones from thermal 1,3-shifts in quinol vinyl ethers. Reactions in nonbenzenoid systems and limitations of the chemistry

  摘要：

  Addition of functionalized organolithium compounds to quinone monoketals furnished 4-hydroxy-2,5-cyclo-hexadienone derivatives. The 4-hydroxyl group of these molecules was then transformed into a vinyl ether, and the thermal [1,3]-shift chemistry of these functionalized vinyl ethers was studied. In dienone derivatives wherein a [3,3]-sigmatropic shift was not stereoelectronically possible, these molecules underwent thermal and photochemical [1,3]-oxygen-to-carbon migration, affording spiro-2,5-cyclohexadienones in good yield. However, for compounds in which the [3,3]-shift involving the vinyl ether was possible, this reaction occurred at or below room temperature. 1,5-Cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate was found to be an especially efficient catalyst for the allyl-to-vinyl ether isomerization in these systems.

  DOI：

  10.1021/jo00021a037
• 作为产物：
  描述：

  8-Pent-3-ynyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ol 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 0.75h， 以73%的产率得到4-(3-pentynyl)-4-hydroxycyclohexa-2,5-dienone
  参考文献：
  名称：

  Spiro-fused 2,5-cyclohexadienones from thermal 1,3-shifts in quinol vinyl ethers. Reactions in nonbenzenoid systems and limitations of the chemistry

  摘要：

  Addition of functionalized organolithium compounds to quinone monoketals furnished 4-hydroxy-2,5-cyclo-hexadienone derivatives. The 4-hydroxyl group of these molecules was then transformed into a vinyl ether, and the thermal [1,3]-shift chemistry of these functionalized vinyl ethers was studied. In dienone derivatives wherein a [3,3]-sigmatropic shift was not stereoelectronically possible, these molecules underwent thermal and photochemical [1,3]-oxygen-to-carbon migration, affording spiro-2,5-cyclohexadienones in good yield. However, for compounds in which the [3,3]-shift involving the vinyl ether was possible, this reaction occurred at or below room temperature. 1,5-Cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate was found to be an especially efficient catalyst for the allyl-to-vinyl ether isomerization in these systems.

  DOI：

  10.1021/jo00021a037