9-phenyl-1,3-dioxadispiro<4.2.4.2>tetradeca-6,13-dien-10-one | 135614-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-phenyl-1,3-dioxadispiro<4.2.4.2>tetradeca-6,13-dien-10-one
• 英文别名: 4-Phenyl-9,12-dioxadispiro[4.2.48.25]tetradeca-6,13-dien-3-one
• CAS: 135614-79-8
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: WXVDLCBBVPEACG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(3-butynyl)-4-hydroxycyclohexa-2,5-dienone dimethyl acetal 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 18-冠醚-6 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 33.0h， 生成 9-phenyl-1,3-dioxadispiro<4.2.4.2>tetradeca-6,13-dien-10-one
  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