4-cyclohexyl-3,3-difluoro-4-hydroxybutan-2-one | 1015236-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-cyclohexyl-3,3-difluoro-4-hydroxybutan-2-one
• CAS: 1015236-54-0
• 化学式: C₁₀H₁₆F₂O₂
• 分子量: 206.233
• InChiKey: XXQZNKACPFHQQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-cyclohexyl-3,3-difluoro-4-hydroxybutan-2-one 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到4-(tert-butyldimethylsilyloxy)-4-cyclohexyl-3,3-difluorobutan-2-one
  参考文献：
  名称：

  Fluoroallylboration−Olefination for the Synthesis of (Z)-4,4-Difluoropent-2-enoates and 5,5-Difluoro-5,6-dihydropyran-2-ones

  摘要：

  Horner-Wadsworth Emmons (HWE) or Still-Gennari olefination of TBS-protected 3,3-difluoro-4-hydroxy-2-ones, derived from the difluoroallylboration of aldehydes, provides the Z-isomer of 4,4,-difluoropent-2-enoates. These, upon hydrolysis, followed by Yamaguchi cyclization, afford 5,5-difluoro-4-methyl-5,6-dihydro-alpha-pyrones in high yields.

  DOI：

  10.1021/ol103097s
• 作为产物：
  描述：

  3-(苄氧基)-1-环己基-2,2-二氟丁-3-烯-1-醇 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以79%的产率得到4-cyclohexyl-3,3-difluoro-4-hydroxybutan-2-one
  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