4-methyl-N-(naphthalen-1-yl)pyridin-2-amine | 1570075-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methyl-N-(naphthalen-1-yl)pyridin-2-amine
• 英文别名: 4-methyl-N-naphthalen-1-ylpyridin-2-amine
• CAS: 1570075-72-7
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: ZTVNRYHDMJOSGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-4-甲基吡啶 、 1-萘胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 双(2-二苯基磷苯基)醚 作用下， 以 甲苯 为溶剂， 以68%的产率得到4-methyl-N-(naphthalen-1-yl)pyridin-2-amine
  参考文献：
  名称：

  Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-N-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications

  摘要：

  The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of H-1 NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.

  DOI：

  10.1021/om401195w

文献信息

• Polyaminopyridines and method for producing same
  申请人：Kanbara Takaki

  公开号：US20060293503A1

  公开（公告）日：2006-12-28

  The present invention provides novel polyaminopyridines which are excellent in solubility in various solvents, and are preferably used in a polymer-type organic electroluminescent material, and a process for preparing the same. More particularly, the present invention provides polyaminopyridines having a repetition structural unit represented by the following general formula (1); and having a number average molecular weight in a range of 500 to 1000000.

  本发明提供了新型的聚氨基吡啶，其在各种溶剂中具有优异的溶解性，并且最好用于聚合物型有机电致发光材料，并提供了制备它们的过程。更具体地，本发明提供了具有以下一般式（1）所表示的重复结构单元的聚氨基吡啶，其具有500至1000000之间的数均分子量。
• POLYAMINOPYRIDINES AND METHOD FOR PRODUCING SAME
  申请人：SUMITOMO SEIKA CHEMICALS CO., LTD.

  公开号：EP1669390A1

  公开（公告）日：2006-06-14

  The present invention provides novel polyaminopyridines which are excellent in solubility in various solvents, and are preferably used in a polymer-type organic electroluminescent material, and a process for preparing the same. More particularly, the present invention provides polyaminopyridines having a repetition structural unit represented by the following general formula (1); and having a number average molecular weight in a range of 500 to 1000000.

  本发明提供了在各种溶剂中溶解性极佳的新型聚氨基吡啶，优选用于聚合物型有机电致发光材料，并提供了制备该材料的工艺。更具体地说，本发明提供了具有以下通式（1）所代表的重复结构单元的聚氨基吡啶； 且平均分子量在 500 至 1000000 之间。
• Palladium(II)-Catalyzed Direct Ortho Arylation of 4-Methyl-<i>N</i>-phenylpyridin-2-amines via C–H Activation/C–C Coupling and Synthetic Applications
  作者：Jean-Ho Chu、Hao-Ping Huang、Wen-Ting Hsu、Shih-Tien Chen、Ming-Jung Wu

  DOI：10.1021/om401195w

  日期：2014.3.10

  The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of H-1 NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.