(1R,3S)-2,2-difluoro-1-phenylbutane-1,3-diol

• 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: (1R,3S)-2,2-difluoro-1-phenylbutane-1,3-diol
• 化学式: C₁₀H₁₂F₂O₂
• 分子量: 202.201
• InChiKey: MIYXYHIPNUSMKR-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3-difluoro-4-hydroxy-4-phenyl-2-butanone 在 四甲基乙二胺 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 反应 8.0h， 生成 (1R,3S)-2,2-difluoro-1-phenylbutane-1,3-diol 、 (1R,3R)-2,2-difluoro-1-phenylbutane-1,3-diol
  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

• Asymmetric Fluoroallylboration of Aldehydes
  作者：P. Veeraraghavan Ramachandran、Agnieszka Tafelska-Kaczmarek、Kaumba Sakavuyi

  DOI：10.1021/ol201551y

  日期：2011.8.5

  provides a series of chiral γ,γ-difluoroallylboronates. Asymmetric fluoroallylboration of aldehydes with a 2-phenylbornane-2,3-diol-derived reagent provides gem-difluorinated homoallyl alcohols in good yields and 77–95% ee. Preparation of a chiral α-pyrone in >99% ee has also been described.

  与先前的报道相反，苄氧基二氟乙烯基锂与大体积的手性碘甲基硼酸酯的同系物容易提供一系列手性的γ，γ-二氟烯丙基硼酸酯。醛与2-苯基硼烷-2,3-二醇衍生的试剂进行不对称的氟代烯丙基氟合成，可得到良好的收率和77-95％ee的宝石二氟代均烯丙基醇。还描述了在> 99％ee中制备手性α-吡喃酮的方法。