N-(1-Cyano-2,2,2-trifluoroethyl)-N-ethylaniline | 110972-20-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(1-Cyano-2,2,2-trifluoroethyl)-N-ethylaniline
• 英文别名: 2-(Ethylanilino)-3,3,3-trifluoropropanenitrile；2-(N-ethylanilino)-3,3,3-trifluoropropanenitrile
• CAS: 110972-20-8
• 化学式: C₁₁H₁₁F₃N₂
• 分子量: 228.217
• InChiKey: DEKXZJZOKOARLW-UHFFFAOYSA-N

物化性质

• 沸点：
  266.9±40.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-ethyl-2,2,2-trifluoro-N-phenylacetamide 在 氢氧化钾 、 dimethyl sulfide borane 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-(1-Cyano-2,2,2-trifluoroethyl)-N-ethylaniline
  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

• Fuchigami, Toshio; Ichikawa, Shinji; Konno, Akinori, Chemistry Letters, 1989, p. 1987 - 1988
  作者：Fuchigami, Toshio、Ichikawa, Shinji、Konno, Akinori

  DOI：——

  日期：——
• Electrolytic transformation of fluoroorganic compounds. 3. Highly regioselective anodic methoxylation of N-(2,2,2-trifluoroethyl)amines
  作者：Toshio Fuchigami、Yuuki Nakagawa、Tsutomu Nonaka

  DOI：10.1021/jo00233a043

  日期：1987.11
• 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.