(E)-1,1,1,5,5,5-hexafluoro-2-phenylpent-3-en-2-ol | 134391-61-0

• 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: (E)-1,1,1,5,5,5-hexafluoro-2-phenylpent-3-en-2-ol
• 英文别名: 2-phenyl-1,1,1,5,5,5-hexafluoropent-3-en-2-ol
• CAS: 134391-61-0
• 化学式: C₁₁H₈F₆O
• 分子量: 270.174
• InChiKey: KKIIBOHFEZRJAK-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1,5,5,5-hexafluoro-2-phenylpent-3-en-2-ol 在 甲烷磺酸 、 phosphorus pentoxide 作用下， 反应 2.0h， 以76%的产率得到1,3-bis(trifluoromethyl)indene
  参考文献：
  名称：

  Synthesis of perfluoroalkylated indenes

  摘要：

  A series of perfluoroalkylated indenes has been synthesized using four different synthetic pathways. 1-(Pentafluoroethyl)indene and 2-(pentafluoroethyl)indene were prepared by the addition of (pentafluoroethyl)lithium to the appropriate ketones and subsequent dehydration. 2-(Trifluoromethyl)indene was synthesized through the photoinduced addition of trifluoromethyl iodide to indene, followed by dehydroiodination. 1-(Trifluoromethyl)indene was prepared by the addition of (trifluoromethyl)trimethylsilane to 1-indanone followed by deprotection and dehydration and by the sigmatropic cyclization of the appropriate phenylvinyl carbocation. This latter approach was also used to synthesize 1,3-bis(trifluoromethyl)indene and 1,2,3-tris(trifluoromethyl)indene.

  DOI：

  10.1021/jo00017a029
• 作为产物：
  描述：

  2,2,2-三氟苯乙酮 在 叔丁基过氧化氢 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 癸烷 、 乙腈 、 mineral oil 为溶剂， 反应 2.0h， 生成 (E)-1,1,1,5,5,5-hexafluoro-2-phenylpent-3-en-2-ol
  参考文献：
  名称：

  炔烃的过渡金属自由基自由基氢三氟甲基化

  摘要：

  容易获得且稳定的CF 3 SO 2 Na和t BuOOH的组合有效地用于炔烃的加氢三氟甲基化。在烯烃的合成中表现出优异的反选择性。发达的温和反应条件可以抑制竞争性的Meyer–Schuster型重排。

  DOI：

  10.1002/ejoc.201800291

文献信息

• Regioselective Nucleophilic 1,4-Trifluoromethylation of 2-Polyfluoroalkylchromones with (Trifluoromethyl)trimethylsilane. Synthesis of Fluorinated Analogs of Natural 2,2-Dimethylchroman-4-ones and 2,2-Dimethylchromenes
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Dmitri V. Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1021/jo034591y

  日期：2003.10.1

  Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.