2-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-2,3-dihydro-4H-chromen-4-one

• 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: 2-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-2,3-dihydro-4H-chromen-4-one
• 英文别名: 2-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-3H-chromen-4-one
• 化学式: C₁₁H₈F₄O₃
• 分子量: 264.176
• InChiKey: LBUFHPUAFQVEFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-(1,1,2,2-tetrafluoroethyl)-2,3-dihydro-4H-chromen-4-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以90%的产率得到3-(2-Hydroxy-phenyl)-5-(1,1,2,2-tetrafluoro-ethyl)-4,5-dihydro-isoxazol-5-ol
  参考文献：
  名称：

  摘要：

  The reactions of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydroxylamine yield, through Delta(2)-isoxazolines as intermediate products, 3-(2-hydroxyaryl)-5-polyfluoroalkylisoxazoles. Analogous reactions with 2-polyfluoroalkylchromones afford beta-diketone monooximes, which in an acidic medium undergo cyclode hydration into 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles. The structures of regioisomeric 3- and 5-polyfluoroalkylisoxazoles were determined using H-1, F-19, and C-13 NMR spectroscopy.

  DOI：

  10.1023/a:1020908831426

文献信息

• A Novel and Convenient Synthesis of 3-(Polyhaloacyl)chromones Using Diethoxymethyl Acetate
  作者：Vyacheslav Ya. Sosnovskikh、Roman A. Irgashev

  DOI：10.1055/s-2005-865199

  日期：——

  The reaction of 2-hydroxy-2-(polyhaloalkyl)chroman-4-ones with diethoxymethyl acetate readily occurs at 140-150 °C for 15 minutes to give 3-(polyhaloacyl)chromones in good yields.

  2-羟基-2-(多卤代烷基)色满-4-酮与乙酸二乙氧基甲酯的反应很容易在140-150°C下反应15分钟，以良好的产率得到3-(多卤代酰基)色酮。
• ——
  作者：V. Ya. Sosnovskikh、M. A. Barabanov、A. Yu. Sizov

  DOI：10.1023/a:1020960815497

  日期：——

  The reaction of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydrazine affords 5-hydroxy-3-(2-hydroxyaryl)-5-polyfluoroalkyl-Delta(2)-pyrazolines, whereas 2-polyfluoroalkylchromones under similar conditions produce 3(5)-(2-hydroxyaryl)-5(3)-polyfluoroalkylpyrazoles. 5 - (2-Hydroxyaryl)-1-methyl-3-polyfluoroalkylpyrazoles were synthesized in the reaction with methylhydrazine, and the reaction with phenylhydrazine afforded regioisomeric 3(5)-(2-hydroxyphenyl)-1-phenyl-5(3)-polyfluoroalkylpyrazoles.
• ——
  作者：V. Ya. Sosnovskikh、A. Yu. Sizov、B. I. Usachev

  DOI：10.1023/a:1020908831426

  日期：——

  The reactions of 2-hydroxy-2-polyfluoroalkylchroman-4-ones with hydroxylamine yield, through Delta(2)-isoxazolines as intermediate products, 3-(2-hydroxyaryl)-5-polyfluoroalkylisoxazoles. Analogous reactions with 2-polyfluoroalkylchromones afford beta-diketone monooximes, which in an acidic medium undergo cyclode hydration into 5-(2-hydroxyaryl)-3-polyfluoroalkylisoxazoles. The structures of regioisomeric 3- and 5-polyfluoroalkylisoxazoles were determined using H-1, F-19, and C-13 NMR spectroscopy.