6-methyl-2,2-bis(trifluoromethyl)chroman-4-one | 540726-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one
• 英文别名: 6-methyl-2,2-bis(trifluoromethyl)-3H-chromen-4-one
• CAS: 540726-58-7
• 化学式: C₁₂H₈F₆O₂
• 分子量: 298.185
• InChiKey: VUDPNBGFUHGGMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-methyl-2,2-bis(trifluoromethyl)chroman-4-one 在 dipotassium peroxodisulfate 、 copper(II) sulfate 作用下， 以 水 、 乙腈 为溶剂， 以35%的产率得到4-oxo-2,2-bis(trifluoromethyl)chroman-6-carboxylic acid
  参考文献：
  名称：

  The first example of a preparative 1,4-perfluoroalkylation using (perfluoroalkyl)trimethylsilanes

  摘要：

  Reactions of 2-perfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(perfluoroalkyl)chroman-4-ones in high yields after acid hydrolysis. Oxidation of 2,2-bis(trifluoromethyl)-6-methylchroman-4-one with K2S2O8 leads to fluorinated analogs of natural lactarochromal and the corresponding acid. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)00184-9
• 作为产物：
  描述：

  6-methyl-2-trifluoromethyl-chromen-4-one 、 (三氟甲基)三甲基硅烷 在 四甲基氟化铵 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以61%的产率得到6-methyl-2,2-bis(trifluoromethyl)chroman-4-one
  参考文献：
  名称：

  The first example of a preparative 1,4-perfluoroalkylation using (perfluoroalkyl)trimethylsilanes

  摘要：

  Reactions of 2-perfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(perfluoroalkyl)chroman-4-ones in high yields after acid hydrolysis. Oxidation of 2,2-bis(trifluoromethyl)-6-methylchroman-4-one with K2S2O8 leads to fluorinated analogs of natural lactarochromal and the corresponding acid. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)00184-9

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.
• The first example of a preparative 1,4-perfluoroalkylation using (perfluoroalkyl)trimethylsilanes
  作者：V.Ya Sosnovskikh、D.V Sevenard、B.I Usachev、G.-V Röschenthaler

  DOI：10.1016/s0040-4039(03)00184-9

  日期：2003.3

  Reactions of 2-perfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(perfluoroalkyl)chroman-4-ones in high yields after acid hydrolysis. Oxidation of 2,2-bis(trifluoromethyl)-6-methylchroman-4-one with K2S2O8 leads to fluorinated analogs of natural lactarochromal and the corresponding acid. (C) 2003 Published by Elsevier Science Ltd.