1,5-diphenyl-3-trifluoromethyl-penta-1,4-dien-3-ol | 1536-02-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 1,5-diphenyl-3-trifluoromethyl-penta-1,4-dien-3-ol
• 英文别名: 1,5-Diphenyl-3-trifluormethyl-penta-1,4-dien-3-ol；(1E,4E)-1,5-diphenyl-3-(trifluoromethyl)penta-1,4-dien-3-ol
• CAS: 1536-02-3
• 化学式: C₁₈H₁₅F₃O
• 分子量: 304.312
• InChiKey: LMOMTERBOGENTA-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  联甲基苯乙烯酮 在 四丁基氟化铵 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 1,5-diphenyl-3-trifluoromethyl-penta-1,4-dien-3-ol
  参考文献：
  名称：

  来自氨基醇的三氟乙酰胺作为亲核三氟甲基化试剂。

  摘要：

  DOI：

  10.1002/anie.200351301

文献信息

• Trifluoromethanesulfinamide from Ephedrine: A More Efficient Trifluoro-methylating Reagent
  作者：Thierry Billard、Bernard R. Langlois、Solveig Roussel、Laurent Saint-Jalmes

  DOI：10.1055/s-2004-831322

  日期：——

  Nucleophilic trifluoromethylation of non-enolizable and enolizable carbonyl compounds was achieved with the trifluoromethanesulfinamide derived from O-silylated ephedrine. In contrast to the trifluoroacetamide analog, previously described, this reagent is able to trifluoromethylate more acidic enolizable compounds.

  非烯醇化和烯醇化羰基化合物的亲核三氟甲基化是用衍生自 O-硅烷化麻黄碱的三氟甲亚磺酰胺实现的。与之前描述的三氟乙酰胺类似物相比，该试剂能够使酸性更强的可烯醇化化合物三氟甲基化。
• 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.
• Neunhoeffer et al., Chemische Berichte, 1959, vol. 92, p. 252,255
  作者：Neunhoeffer et al.

  DOI：——

  日期：——
• Trifluoroacetamides from Amino Alcohols as Nucleophilic Trifluoromethylating Reagents
  作者：Jérôme Joubert、Solveig Roussel、Carole Christophe、Thierry Billard、Bernard R. Langlois、Thierry Vidal

  DOI：10.1002/anie.200351301

  日期：2003.7.14