4,4,4-trifluoro-3-N,N-dimethylamino-1-phenyl-1-butanone | 325704-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-trifluoro-3-N,N-dimethylamino-1-phenyl-1-butanone
• 英文别名: N,N-dimethyl-1-trifluoromethyl-2-benzoylethylamine；3-(Dimethylamino)-4,4,4-trifluoro-1-phenylbutan-1-one
• CAS: 325704-95-8
• 化学式: C₁₂H₁₄F₃NO
• 分子量: 245.244
• InChiKey: LREFYSCMVXIRNB-UHFFFAOYSA-N

物化性质

• 沸点：
  269.0±40.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,4,4-trifluoro-3-N,N-dimethylamino-1-phenyl-1-butanone 在 盐酸 作用下， 生成 (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one
  参考文献：
  名称：

  Nucleophilic Trifluoromethylation of Carbonyl Compounds and Disulfides with Trifluoromethane and Silicon-Containing Bases

  摘要：

  Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)(2)N- M+, generated in situ from N(TMS)(3) and M+ F- or RO- Na+ When F- is used ina catalytic amount, silylated alpha-(trifluoromethyl)carbinols are-obtained: in this case, the four-component system HCF3/N(TMS)(3)/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)(3)/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of aryl disulfides whereas N(SiMe3)(3)/F- is well suited to that of aliphatic disulfides.

  DOI：

  10.1021/jo000150s
• 作为产物：
  描述：

  三氟甲烷 、 3 - （二甲氨基）- 1 -苯基 -2-丙烯-1-酮 在 三(三甲基硅)胺 、 四甲基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4,4,4-trifluoro-3-N,N-dimethylamino-1-phenyl-1-butanone
  参考文献：
  名称：

  Nucleophilic Trifluoromethylation of Carbonyl Compounds and Disulfides with Trifluoromethane and Silicon-Containing Bases

  摘要：

  Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)(2)N- M+, generated in situ from N(TMS)(3) and M+ F- or RO- Na+ When F- is used ina catalytic amount, silylated alpha-(trifluoromethyl)carbinols are-obtained: in this case, the four-component system HCF3/N(TMS)(3)/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)(3)/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of aryl disulfides whereas N(SiMe3)(3)/F- is well suited to that of aliphatic disulfides.

  DOI：

  10.1021/jo000150s

文献信息

• Nucleophilic Trifluoromethylation of Carbonyl Compounds and Disulfides with Trifluoromethane and Silicon-Containing Bases
  作者：Sylvie Large、Nicolas Roques、Bernard R. Langlois

  DOI：10.1021/jo000150s

  日期：2000.12.1

  Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)(2)N- M+, generated in situ from N(TMS)(3) and M+ F- or RO- Na+ When F- is used ina catalytic amount, silylated alpha-(trifluoromethyl)carbinols are-obtained: in this case, the four-component system HCF3/N(TMS)(3)/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)(3)/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of aryl disulfides whereas N(SiMe3)(3)/F- is well suited to that of aliphatic disulfides.