2-fluoro-N-methyl-N-(2-nitrophenyl)aniline | 908242-57-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-fluoro-N-methyl-N-(2-nitrophenyl)aniline
• 英文别名: N-(2-fluorophenyl)-N-methyl-2-nitroaniline
• CAS: 908242-57-9
• 化学式: C₁₃H₁₁FN₂O₂
• 分子量: 246.241
• InChiKey: SYLVSXRBNWVWEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-fluoro-N-methyl-N-(2-nitrophenyl)aniline 在 盐酸 、 钾硼氢 、 potassium hydride 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 copper(l) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.17h， 生成 N-methyl-2-(10-methylphenazin-5(10H)-yl)aniline hydrochloride
  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-硝基苯胺 在 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 25.0h， 生成 2-fluoro-N-methyl-N-(2-nitrophenyl)aniline
  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

文献信息

• A Route to Regioselectively Functionalized Carbazoles, Dibenzofurans, and Dibenzothiophenes through Anionic Cyclization of Benzyne-Tethered Aryllithiums
  作者：Roberto Sanz、Yolanda Fernández、M Pilar Castroviejo、Antonio Pérez、Francisco J. Fañanás

  DOI：10.1021/jo060911c

  日期：2006.8.1

  available products, with 3.3 equiv of t-BuLi and further reaction with selected electrophiles gives rise to functionalized carbazole, dibenzofuran, and dibenzothiophene derivatives in a direct and regioselective manner. The process involves an anionic cyclization on a benzyne-tethered aryllithium intermediate.

  用3.3当量的t- BuLi处理易于从市售产品中制备的2-氟苯基2-碘苯胺，醚和硫醚，然后与选定的亲电试剂进一步反应，可以直接和直接生成官能化的咔唑，二苯并呋喃和二苯并噻吩衍生物。区域选择性方式。该方法涉及在苯炔系留的芳基锂中间体上进行阴离子环化。