3,5,5-trimethylcyclopent-2-en-1-ol | 1215117-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5,5-trimethylcyclopent-2-en-1-ol
• 英文别名: 3,5,5-Trimethylcyclopent-2-en-1-ol
• CAS: 1215117-77-3
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: NVUPTTJEJBCTMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  3,5,5-trimethylcyclopent-2-en-1-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 以62%的产率得到3,3,5-trimethyl-6-oxabicyclo[3.1.0]hexan-2-ol
  参考文献：
  名称：

  Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one

  摘要：

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.

  DOI：

  10.1002/hlca.200900231
• 作为产物：
  描述：

  3,5,5-三甲基-2-环戊烯-1-酮 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 乙醚 为溶剂， 以88%的产率得到3,5,5-trimethylcyclopent-2-en-1-ol
  参考文献：
  名称：

  Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one

  摘要：

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.

  DOI：

  10.1002/hlca.200900231

文献信息

• Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one
  作者：Christian Chapuis、Christine Saint-Léger

  DOI：10.1002/hlca.200900231

  日期：2010.1

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.