(-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-ethynylbicyclo[2.2.1]heptane | 406688-58-2

• 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: (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-ethynylbicyclo[2.2.1]heptane
• 英文别名: (-)-(1S,2S,4R)-2-ethynyl-7,7-dimethyl-1-vinylbicyclo[2.2.1]heptan-2-ol；(1S,2S,4R)-1-ethenyl-2-ethynyl-7,7-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 406688-58-2
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: SITMLPAJZBEKJC-RAIGVLPGSA-N

物化性质

• 沸点：
  219.1±19.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-ethynylbicyclo[2.2.1]heptane 在 mercury(II) diacetate 、 mercury(II) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到1,4-bis[(1S,2S,4R)-2-hydroxy-7,7-dimethyl-1-vinylbicyclo[2.2.1]heptan-2-yl]buta-1,3-diyne
  参考文献：
  名称：

  摘要：

  Vinylbornylacetylenes and their trimethylsilyl derivatives undergo oxidative dimerization in the presence of an Hg(OAc)(2)-HgO system in MeOH to give the corresponding diacetylenes.

  DOI：

  10.1023/a:1014058823747
• 作为产物：
  描述：

  7,7-dimethyl-1-vinylbicyclo[2.2.1]heptan-2-one 、 乙炔 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以90%的产率得到(-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-ethynylbicyclo[2.2.1]heptane
  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

• 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
  作者：N. S. Vostrikov、V. Z. Vasikov、L. V. Akulova、A. A. Fatykhov、S. L. Khursan、L. V. Spirikhin、M. S. Miftakhov

  DOI：10.1134/s1070428006060042

  日期：2006.6

  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.
• 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.