2-methyl-2'-(4-methoxyphenyl)bis(1,2,2-trifluoroethyl)ether

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methyl-2'-(4-methoxyphenyl)bis(1,2,2-trifluoroethyl)ether
• 英文别名: 1-methoxy-4-[(2S)-1,1,2-trifluoro-2-[(1S)-1,2,2-trifluoropropoxy]ethyl]benzene
• 化学式: C₁₂H₁₂F₆O₂
• 分子量: 302.216
• InChiKey: VMOIKHLZCIXITA-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)-2-氧代乙醛 、 丙酮醛 在 水 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以18%的产率得到2-methyl-2'-(4-methoxyphenyl)bis(1,2,2-trifluoroethyl)ether
  参考文献：
  名称：

  Polyfluoroether Derivatives via Nucleophilic Fluorination of Glyoxal Hydrates with Deoxofluor

  摘要：

  Various glyoxal hydrates have been reacted with Deoxofluor [(CH3OCH2CH2)(2)NSF3]. In concentrated solutions of dichloromethane, Deoxofluor (1) efficiently fluorinates a variety of glyoxal hydrates, RCOCHO.H2O (R = 4-methoxyphenyl, 3,4-methylenedioxyphenyl, 4-methylphenyl, 4-fluorophenyl, phenyl, 2-thienyl, methyl) (6a-g) to form polyfluoroethers 7a-g and 8a-g as meso and racemic mixtures (similar to1:1) in good yields. The meso and racemic compounds were separated by flash chromatography and characterized. When the reactant comprised two different. glyoxal hydrates, mixed polyfluoroethers (9h-j) were observed as the major products. The yields of the mixed polyfluoroethers depend on the ratio of the two different glyoxal hydrates used. Reactions of some other hydrates, such as hydrindantin dehydrate (10) and 1,1,1,5,5,5-hexafluoro-2,2,4,4-pentanetetrol (11), were also studied with Deoxofluor to give a cyclic polyfluoroether (12) and beta-ketoamine (13), respectively. When the reactions of 6a-d were carried out under very dilute conditions, difluoro aldehydes (14a-d) or tetrafluoroalkanes (15a-d) were formed rather than polyfluoroethers. Reactions of concentrated solutions of nonhydrated glyoxals (16k-m) in methylene chloride with Deoxofluor produced the tetrafluoroalkanes (18k-m) in good yields with only trace amounts of difluoroaldehydes (17k-m) being found. The structures of 7a (meso), 8b (racemic), and 12 have been confirmed by single-crystal X-ray analysis.

  DOI：

  10.1021/jo016245r

文献信息

• Polyfluoroether Derivatives via Nucleophilic Fluorination of Glyoxal Hydrates with Deoxofluor
  作者：Rajendra P. Singh、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/jo016245r

  日期：2002.3.1

  Various glyoxal hydrates have been reacted with Deoxofluor [(CH3OCH2CH2)(2)NSF3]. In concentrated solutions of dichloromethane, Deoxofluor (1) efficiently fluorinates a variety of glyoxal hydrates, RCOCHO.H2O (R = 4-methoxyphenyl, 3,4-methylenedioxyphenyl, 4-methylphenyl, 4-fluorophenyl, phenyl, 2-thienyl, methyl) (6a-g) to form polyfluoroethers 7a-g and 8a-g as meso and racemic mixtures (similar to1:1) in good yields. The meso and racemic compounds were separated by flash chromatography and characterized. When the reactant comprised two different. glyoxal hydrates, mixed polyfluoroethers (9h-j) were observed as the major products. The yields of the mixed polyfluoroethers depend on the ratio of the two different glyoxal hydrates used. Reactions of some other hydrates, such as hydrindantin dehydrate (10) and 1,1,1,5,5,5-hexafluoro-2,2,4,4-pentanetetrol (11), were also studied with Deoxofluor to give a cyclic polyfluoroether (12) and beta-ketoamine (13), respectively. When the reactions of 6a-d were carried out under very dilute conditions, difluoro aldehydes (14a-d) or tetrafluoroalkanes (15a-d) were formed rather than polyfluoroethers. Reactions of concentrated solutions of nonhydrated glyoxals (16k-m) in methylene chloride with Deoxofluor produced the tetrafluoroalkanes (18k-m) in good yields with only trace amounts of difluoroaldehydes (17k-m) being found. The structures of 7a (meso), 8b (racemic), and 12 have been confirmed by single-crystal X-ray analysis.