N-(4-methoxyphenyl)-4-methylpyridin-2-amine | 1260824-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-methoxyphenyl)-4-methylpyridin-2-amine
• CAS: 1260824-44-9
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: ZLRUULOKURJFHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-4-methylpyridin-2-amine 在 甲酸 、 二乙酰二(三苯基膦)钯 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 6.5h， 以80%的产率得到8-Methoxy-3-methylpyrido[1,2-a]benzimidazole
  参考文献：
  名称：

  钯催化的电化学氧化CH-H胺用于合成并析出氢的吡啶并[1,2- a ]苯并咪唑

  摘要：

  过渡金属催化的C–H / N–H氧化偶联反应是构建C–N键的重要方法。但是，通常需要化学计量的氧化剂。在这里，我们报道了没有外部氧化剂或添加剂的钯催化的电氧化分子内CH / NH环化反应。通过简单，绿色和温和的途径构建了各种吡啶并[1,2- a ]苯并咪唑。实验结果表明，Pd（0）可以在阳极上被氧化再利用。

  DOI：

  10.1021/acscatal.0c00103
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 、 甲氧苯胺 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88%的产率得到N-(4-methoxyphenyl)-4-methylpyridin-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

• 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.
• Palladium-Catalyzed Electro-oxidative C–H Amination toward the Synthesis of Pyrido[1,2-<i>a</i>]benzimidazoles with Hydrogen Evolution
  作者：Zhengli Duan、Lin Zhang、Wenxin Zhang、Lijun Lu、Li Zeng、Renyi Shi、Aiwen Lei

  DOI：10.1021/acscatal.0c00103

  日期：2020.3.20

  stoichiometric oxidants were usually necessary. Here, we report a palladium-catalyzed electro-oxidative intramolecular C–H/N-H annulation reaction without an external oxidant or additive. A variety of pyrido[1,2-a]benzimidazoles were constructed by a simple, green, and mild path. Experimental results suggested that Pd(0) could be oxidized on the anode to be recycled.

  过渡金属催化的C–H / N–H氧化偶联反应是构建C–N键的重要方法。但是，通常需要化学计量的氧化剂。在这里，我们报道了没有外部氧化剂或添加剂的钯催化的电氧化分子内CH / NH环化反应。通过简单，绿色和温和的途径构建了各种吡啶并[1,2- a ]苯并咪唑。实验结果表明，Pd（0）可以在阳极上被氧化再利用。