2-(8-Phenyl-1,4-dioxa-spiro[4.5]deca-7,9-dien-6-yl)-propionaldehyde | 135639-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(8-Phenyl-1,4-dioxa-spiro[4.5]deca-7,9-dien-6-yl)-propionaldehyde
• 英文别名: 2-(8-phenyl-1,4-dioxaspiro[4.5]deca-7,9-dien-6-yl)propanal
• CAS: 135639-25-7
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: VVVGFWYHPYUUFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(8-Phenyl-1,4-dioxa-spiro[4.5]deca-7,9-dien-6-yl)-propionaldehyde 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(2-hydroxyethoxy)-2-(1-oxopropyl)biphenyl
  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：

  4-phenyl-4-(allyloxy)cyclohexa-2,5-dienone ethylene acetal 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 2-(8-Phenyl-1,4-dioxa-spiro[4.5]deca-7,9-dien-6-yl)-propionaldehyde
  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