1-cyclopropyl-1-(1-naphthyl)ethanol | 917100-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-cyclopropyl-1-(1-naphthyl)ethanol
• 英文别名: 1-Cyclopropyl-1-naphthalen-1-ylethanol
• CAS: 917100-94-8
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: XGLJMMCYURFDPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-1-(1-naphthyl)ethanol 在 高氯酸 、 氧气 、 亚甲兰 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 47.0h， 生成 3-hydroperoxy-4-(1-naphthyl)pent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹

  摘要：

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.

  DOI：

  10.1021/jo061414z
• 作为产物：
  描述：

  环丙甲基酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以55%的产率得到1-cyclopropyl-1-(1-naphthyl)ethanol
  参考文献：
  名称：

  Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹

  摘要：

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.

  DOI：

  10.1021/jo061414z