diisopropyl 2-(benzyloxy)-3,3-difluoroallylboronate | 1015236-34-6

• 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: diisopropyl 2-(benzyloxy)-3,3-difluoroallylboronate
• 英文别名: diisopropyl β-(benzyloxy)-γ,γ-difluoroallylboronate；(3,3-Difluoro-2-phenylmethoxyprop-2-enyl)-di(propan-2-yloxy)borane
• CAS: 1015236-34-6
• 化学式: C₁₆H₂₃BF₂O₃
• 分子量: 312.165
• InChiKey: ANNPKZSXQTYYCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五氟苯甲醛 、 diisopropyl 2-(benzyloxy)-3,3-difluoroallylboronate 以 正戊烷 为溶剂， 反应 0.08h， 以72%的产率得到3-(苄氧基)-2,2-二氟-1-(全氟苯基)丁-3-烯-1-醇
  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
• 作为产物：
  描述：

  1-苄氧基-2,2-二氟乙烯 、 diisopropyl iodomethylboronate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 diisopropyl 2-(benzyloxy)-3,3-difluoroallylboronate
  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

• Facile allylboration of ketones with β-benzyloxy-γ,γ-difluoroallylboronate: Preparation of gem-difluorinated homoallylic tert-alcohols
  作者：P. Veeraraghavan Ramachandran、Anamitra Chatterjee

  DOI：10.1016/j.jfluchem.2008.09.014

  日期：2009.2

  The reaction of beta-benzyloxy-gamma,gamma-difluoroallylboronate, at room temperature and in the absence of catalysts, with a variety of aromatic and aliphatic ketones of varying sterics and electronic requirements furnishes fluorinated homoallylic tert-alcohols in 62-82% yields. Representatives of these alcohols were converted to their corresponding alpha,alpha-difluoro-beta-hydroxy ketones in 73-85% yields. (C) 2008 Elsevier B.V. All rights reserved.
• <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.