(E)-1,1,1,3,3-pentafluoro-6-phenylhex-5-ene-2,2,4-triol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1,1,1,3,3-pentafluoro-6-phenylhex-5-ene-2,2,4-triol
• 化学式: C₁₂H₁₁F₅O₃
• 分子量: 298.21
• InChiKey: QFPBHJNARAWZGU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1,3,3-pentafluoro-6-phenylhex-5-ene-2,2,4-triol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以41%的产率得到(E)-4,4,6,6,6-pentafluoro-5,5-dihydroxy-1-phenylhex-1-en-3-one
  参考文献：
  名称：

  Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones

  摘要：

  2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones are valuable precursors to difluoroenolates following fragmentation during the release of trifluoroacetate; however, there are few synthetic strategies to prepare this unique class of compound. We addressed this issue and report a mild, two-step synthesis of 2,2,4,4,4-pentafluoro-3,3-dihydroxyketones from aldehydes. Specifically, aldehydes are treated with pentafluoropropen-2-olate, generated from a new fragmentation of hexafluoroisopropanol with a mixed Mg/Li amide, to give pentafluoroalcohols. A subsequent oxidation with Dess-Martin periodinane provides the targets in good isolated yields.

  DOI：

  10.1021/acs.joc.6b02863
• 作为产物：
  描述：

  反式肉桂醛 、 六氟异丙醇 在 i-Pr₂NMgCl 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以52%的产率得到(E)-1,1,1,3,3-pentafluoro-6-phenylhex-5-ene-2,2,4-triol
  参考文献：
  名称：

  Generation of Magnesium Pentafluoropropen-2-olate from Hexafluoroisopropanol and Synthesis of 2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones

  摘要：

  2,2,4,4,4-Pentafluoro-3,3-dihydroxyketones are valuable precursors to difluoroenolates following fragmentation during the release of trifluoroacetate; however, there are few synthetic strategies to prepare this unique class of compound. We addressed this issue and report a mild, two-step synthesis of 2,2,4,4,4-pentafluoro-3,3-dihydroxyketones from aldehydes. Specifically, aldehydes are treated with pentafluoropropen-2-olate, generated from a new fragmentation of hexafluoroisopropanol with a mixed Mg/Li amide, to give pentafluoroalcohols. A subsequent oxidation with Dess-Martin periodinane provides the targets in good isolated yields.

  DOI：

  10.1021/acs.joc.6b02863