N¹-(2-aminophenyl)-N²-(2-fluorophenyl)-N¹,N²-dimethylbenzene-1,2-diamine | 1429049-10-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹-(2-aminophenyl)-N²-(2-fluorophenyl)-N¹,N²-dimethylbenzene-1,2-diamine
• 英文别名: 2-N-[2-(2-fluoro-N-methylanilino)phenyl]-2-N-methylbenzene-1,2-diamine
• CAS: 1429049-10-4
• 化学式: C₂₀H₂₀FN₃
• 分子量: 321.397
• InChiKey: JKKJVUMONJOOMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹-(2-aminophenyl)-N²-(2-fluorophenyl)-N¹,N²-dimethylbenzene-1,2-diamine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 N-methyl-2-(10-methylphenazin-5(10H)-yl)aniline tosylate
  参考文献：
  名称：

  Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate

  摘要：

  Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.

  DOI：

  10.1021/jo302795w
• 作为产物：
  描述：

  2-氟碘苯 在 钾硼氢 、 potassium hydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 copper(l) chloride 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 55.17h， 生成 N¹-(2-aminophenyl)-N²-(2-fluorophenyl)-N¹,N²-dimethylbenzene-1,2-diamine
  参考文献：
  名称：

  Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate

  摘要：

  Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.

  DOI：

  10.1021/jo302795w