N-(2,2-Difluoroethyl)-N-ethylaniline | 137607-97-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2,2-Difluoroethyl)-N-ethylaniline
• CAS: 137607-97-7
• 化学式: C₁₀H₁₃F₂N
• 分子量: 185.217
• InChiKey: VKXCCBZSKQCJBX-UHFFFAOYSA-N

物化性质

• 沸点：
  225.5±35.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,2-Difluoroethyl)-N-ethylaniline 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-difluoroethyl)-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
• 作为产物：
  描述：

  lithium N-ethylanilide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2,2-Difluoroethyl)-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

• Direct <i>N‐</i> Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition‐Metal‐Free Catalysis
  作者：Chunlei Lu、Zetian Qiu、Maojie Xuan、Yan Huang、Yongjia Lou、Yiling Zhu、Hao Shen、Bo‐Lin Lin

  DOI：10.1002/adsc.202000679

  日期：2020.10.6

  scalable protocol of direct N‐mono/di‐alkyl/fluoroalkylation of primary/secondary amines has been constructed with various carboxylic acids as coupling agents under the catalysis of a simple air‐tolerant inorganic salt, K3PO4. Advantageous features include 100 examples, 10 drugs and drug‐like amines, fluorinated complex tertiary amines, gram‐scale synthesis and isotope‐labelling amine, thus demonstrating

  在简单的耐空气无机盐K 3 PO 4的催化下，已使用各种羧酸作为偶联剂构建了伯/仲胺直接N-单/二烷基/氟烷基化的可扩展方案。有利的特征包括100种实例，10种药物和类药物胺，氟化复杂的叔胺，克级合成和同位素标记胺，因此证明了该方法在工业上的潜在适用性。与减少酰胺中间体所需的传统反应性金属氢化物或硼氢化物相比，反应性较小的氢化硅的参与可能有助于显着的官能团相容性。
• Fuchigami, Toshio; Ichikawa, Shinji; Konno, Akinori, Chemistry Letters, 1989, p. 1987 - 1988
  作者：Fuchigami, Toshio、Ichikawa, Shinji、Konno, Akinori

  DOI：——

  日期：——
• [EN] COMPOUND, COMPOSITION FOR FORMING ANISOTROPIC DYE FILM, ANISOTROPIC DYE FILM, AND OPTICAL ELEMENT<br/>[FR] COMPOSÉ, COMPOSITION POUR CONSTITUER UN FILM DE COLORANT ANISOTROPE, FILM DE COLORANT ANISOTROPE ET ÉLÉMENT OPTIQUE<br/>[JA] 化合物、異方性色素膜形成用組成物、異方性色素膜及び光学素子
  申请人：[en]MITSUBISHI CHEMICAL CORPORATION;[ja]三菱ケミカル株式会社

  公开号：WO2023181907A1

  公开（公告）日：2023-09-28

  下記式（１）で示される化合物。（式（１）中、－Ｘ１は１価の有機基を表す。－Ｒ１１は１つ以上のフッ素原子で置換されたアルキル基を表す。－Ｒ１２は水素原子、アルキル基、又は１つ以上のフッ素原子で置換されたアルキル基を表す。－Ｒ１１及び－Ｒ１２は、一体となって環を形成してもよい。－Ａ１１－、－Ａ１２－、－Ａ１３－及び－Ａ１４－は、それぞれ独立に、置換基を有していてもよい１，４－フェニレン基を表す。）