N-Ethyl-N-(1-methoxy-2,2,2-trifluoroethyl)-α-naphthylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-Ethyl-N-(1-methoxy-2,2,2-trifluoroethyl)-α-naphthylamine
• 英文别名: N-ethyl-N-(2,2,2-trifluoro-1-methoxyethyl)naphthalen-1-amine
• 化学式: C₁₅H₁₆F₃NO
• 分子量: 283.293
• InChiKey: JZTHFZHGZDYQKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  α-乙基氨基萘 在 氢氧化钾 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-Ethyl-N-(1-methoxy-2,2,2-trifluoroethyl)-α-naphthylamine
  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

• Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks
  作者：Toshio Fuchigami、Shinji Ichikawa

  DOI：10.1021/jo00082a018

  日期：1994.2

  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.