4-(1-pentynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal | 135639-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-pentynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal
• 英文别名: 4,4-dimethoxy-1-pent-1-ynylcyclohexa-2,5-dien-1-ol
• CAS: 135639-18-8
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: IFMDMAMXMFHLRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(1-pentynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal 在 potassium salt of 1,3-diaminopropane 作用下， 以 various solvent(s) 为溶剂， 反应 0.08h， 以69%的产率得到4-(4-pentynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal
  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：

  1-戊炔 、 4,4-二甲氧基-2,5-环己二烯-1-酮 在 正丁基锂 作用下， 生成 4-(1-pentynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal
  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