(-)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethan-1-one | 406688-59-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethan-1-one
• 英文别名: (-)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethanone；(-)-(1S,2S,4R)-2-acetyl-1-vinyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptane；(1S,2R,4R)-2-acetyl-1-vinyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptane；1-[(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl]ethanone
• CAS: 406688-59-3
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: QFBJSOZEHOKRHE-RTXFEEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethan-1-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到(1S,3R,5R)-1-ethenyl-3-hydroxy-3,8,8-trimethylbicyclo[3.2.1]octan-2-one
  参考文献：
  名称：

  Double α-ketol rearrangement of (−)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethan-1-one

  摘要：

  The title compound undergoes a-ketol rearrangement by the action of Lewis acids and bases to give the expected and double-rearrangement ring expansion products. Some specific features of the process are discussed.

  DOI：

  10.1134/s1070428006060042
• 作为产物：
  描述：

  (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-ethynylbicyclo[2.2.1]heptane 在 mercury(II) oxide 作用下， 以 硫酸 、 丙酮 为溶剂， 反应 0.5h， 以77%的产率得到(-)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethan-1-one
  参考文献：
  名称：

  摘要：

  Reactions were studied of (-)-(1S,4R)-1-vinyl-7,7-dimethylbicyclo[2.2.1]heptan-2-one with ethyl acetate lithium derivative, potassium acetylide, ozone, with a system OsO4-N-methylmorpholine N-oxide, and some subsequent transformations of the products obtained.

  DOI：

  10.1023/a:1013180012045

文献信息

• Specificity of the reaction of (−)-1-{(1S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}xethanone with ethenylmagnesium bromide
  作者：N. S. Vostrikov、V. Z. Vasikov、M. S. Miftakhov

  DOI：10.1134/s1070428006070050

  日期：2006.7

  Ethenylmagnesium bromide (1.5 equiv) forms a chelate with (-)-1-(S,2R,4R)-1-ethenyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-2-yl}ethanone in THF and promotes its fast primary a-ketol rearrangement into 1-ethenyl-2-hydroxy-2,8,8-trimethylbicyclo[3.2.1]octan-3-one. The latter reacts with excess magnesium reagent (0.5 equiv) according to common 1,2-addition pattern at the carbonyl group and is simultaneously involved in the second alpha-ketol rearrangement which leads to 1-ethenyl-3-hydroxy-3,8,8-trimethylbicyclo-[3.2. 1]octan-2-one as thermodynamically more stable regioisomer.
• Double α-ketol rearrangement of (1S,2R,4R)-2-acetyl-1-vinyl-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptane
  作者：Nikolay S. Vostrikov、Vener Z. Vasikov、Larisa V. Akulova Mansur、S. Miftakhov

  DOI：10.1070/mc2006v016n02abeh002189

  日期：2006.1

  The title compound undergoes an alpha-ketol rearrangement in the NaH-THF and BF3 center dot Et2O-CH2Cl2 systems.