N-ethyl-N-(2,2,2-trifluoroethyl)-p-toluidine | 145577-29-3

• 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: N-ethyl-N-(2,2,2-trifluoroethyl)-p-toluidine
• 英文别名: N-ethyl-4-methyl-N-(2,2,2-trifluoroethyl)aniline
• CAS: 145577-29-3
• 化学式: C₁₁H₁₄F₃N
• 分子量: 217.234
• InChiKey: TZTHFWDTLHTMQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-(2,2,2-trifluoroethyl)-p-toluidine 在 氢氧化钾 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-(1-Cyano-2,2,2-trifluoroethyl)-N-ethyl-p-toluidine
  参考文献：
  名称：

  Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks

  摘要：

  Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH(2)R(f) (R(f) = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position a to the fluoromethyl (R(f)) group, depending on the R(f) and R groups. The effect of the R(f) group on the promotion of the anodic alpha-methoxylation decreased in the order CF3, CHF2, and CH2F. This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the alpha-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines. The alpha-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds alpha to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.

  DOI：

  10.1021/jo00082a018
• 作为产物：
  描述：

  N-乙基对甲苯胺 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-ethyl-N-(2,2,2-trifluoroethyl)-p-toluidine
  参考文献：
  名称：

  Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks

  摘要：

  Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH(2)R(f) (R(f) = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position a to the fluoromethyl (R(f)) group, depending on the R(f) and R groups. The effect of the R(f) group on the promotion of the anodic alpha-methoxylation decreased in the order CF3, CHF2, and CH2F. This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the alpha-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines. The alpha-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds alpha to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.

  DOI：

  10.1021/jo00082a018

文献信息

• Regioselective Carbon-Carbon Bond Formation of 2,2,2-Trifluoroethyl Substituted Tertiary Amines Initiated by Electron Transfer to Photochemically Excited Enone
  作者：Akinori Konno、Toshio Fuchigami

  DOI：10.1246/cl.1992.2181

  日期：1992.11

  Photoadditions of N-(2,2,2-trifluoroethyl)amines to 3-phenylcyclohex-2-en-1-one occurred at the α-position to the trifluoromethyl group predominantly. The regioselectivity of this photoaddition reaction was comparable to that of anodic methoxylation of N-(2,2,2-trifluoroethyl)anilines; this reaction is the first example of direct carbon substitution at α to the trifluoromethyl group and this promotion

  N-(2,2,2-三氟乙基)胺与 3-苯基环己-2-en-1-one 的光加成主要发生在三氟甲基的 α 位。这种光加成反应的区域选择性与 N-(2,2,2-三氟乙基)苯胺的阳极甲氧基化反应相当；该反应是第一个在 α 处碳直接取代三氟甲基的例子，这种促进作用对于其他吸电子基团是普遍的。