α-CF3 hydrocinnamaldehyde | 1180131-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-CF3 hydrocinnamaldehyde
• 英文别名: (S)-2-Benzyl-3,3,3-trifluoropropanal；(2S)-2-benzyl-3,3,3-trifluoropropanal
• CAS: 1180131-27-4
• 化学式: C₁₀H₉F₃O
• 分子量: 202.176
• InChiKey: QIGVSNBDDVFNJC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-CF3 hydrocinnamaldehyde 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 叠氮磷酸二苯酯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 12.0h， 生成 [(R)-1-Benzyl-2,2,2-trifluoroethyl](tert-butoxycarbonyl)amine
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338
• 作为产物：
  描述：

  苯丙醛 、 三氟碘甲烷 在 2,6-二甲基吡啶 、 Ir(ppy)2(dtb-bpy)PF₆ 、 (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one trifluoroacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 α-CF3 hydrocinnamaldehyde
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338

文献信息

• The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
  作者：Anna E. Allen、David W. C. MacMillan

  DOI：10.1021/ja100748y

  日期：2010.4.14

  An enantioselective organocatalytic alpha-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched alpha-trifluoromethylated aldehydes through a nonphotolytic pathway.
• Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis
  作者：David A. Nagib、Mark E. Scott、David W. C. MacMillan

  DOI：10.1021/ja9053338

  日期：2009.8.12

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.