(2S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4,4-difluoro-2-methylhex-5-en-3-ol | 1015236-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4,4-difluoro-2-methylhex-5-en-3-ol
• 英文别名: (2S,3S)-1-[tert-butyl(dimethyl)silyl]oxy-4,4-difluoro-2-methyl-5-phenylmethoxyhex-5-en-3-ol
• CAS: 1015236-46-0
• 化学式: C₂₀H₃₂F₂O₃Si
• 分子量: 386.555
• InChiKey: YCMLMQHQDDOQED-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diisopropyl 2-(benzyloxy)-3,3-difluoroallylboronate 、 (2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal 以 正戊烷 为溶剂， 反应 0.08h， 生成 (2S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4,4-difluoro-2-methylhex-5-en-3-ol 、 (2S)-5-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4,4-difluoro-2-methylhex-5-en-3-ol
  参考文献：
  名称：

  Gem-Difluorinated Homoallyl Alcohols, β-Hydroxy Ketones, and syn- and anti-1,3-Diols via γ,γ-Difluoroallylboronates

  摘要：

  gamma,gamma-Difluoroallylboronates have been prepared from trifluoroethanol and utilized for the allylboration of a variety of aldehydes to provide gem-difluorinated homoallylic alcohols. alpha-Chiral aldehydes were allylborated in 4:1-13:1 diastereoselectivity favoring the anti-isomer. A representative series of difluorinated hydroxyl enol ethers were converted to the corresponding alpha,alpha-difluoro-beta-hydroxy ketones. Diastereoselective reduction of one of these to either syn- and anti-1,3-diol was also studied.

  DOI：

  10.1021/ol800069z

文献信息

• <i>Gem</i>-Difluorinated Homoallyl Alcohols, β-Hydroxy Ketones, and <i>syn</i>- and <i>anti</i>-1,3-Diols via γ,γ-Difluoroallylboronates
  作者：P. Veeraraghavan Ramachandran、Anamitra Chatterjee

  DOI：10.1021/ol800069z

  日期：2008.3.1

  gamma,gamma-Difluoroallylboronates have been prepared from trifluoroethanol and utilized for the allylboration of a variety of aldehydes to provide gem-difluorinated homoallylic alcohols. alpha-Chiral aldehydes were allylborated in 4:1-13:1 diastereoselectivity favoring the anti-isomer. A representative series of difluorinated hydroxyl enol ethers were converted to the corresponding alpha,alpha-difluoro-beta-hydroxy ketones. Diastereoselective reduction of one of these to either syn- and anti-1,3-diol was also studied.