N-[(2,6-dipropylphenyl)methyl]pyridine-2-carboxamide | 1332481-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[(2,6-dipropylphenyl)methyl]pyridine-2-carboxamide
• CAS: 1332481-65-8
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: VDHVTLUQMRNQJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzyl-2-pyridinecarboxamide 、 1-碘代丙烷 在 氧气 、 palladium diacetate 、 三氟甲磺酸钠 、 potassium carbonate 作用下， 以 2-甲基-2-丁醇 为溶剂， 125.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 以99%的产率得到N-[(2,6-dipropylphenyl)methyl]pyridine-2-carboxamide
  参考文献：
  名称：

  Palladium-Catalyzed Alkylation of ortho-C(sp²)–H Bonds of Benzylamide Substrates with Alkyl Halides

  摘要：

  A highly efficient and generally applicable method has been developed to functionalize the ortho-C(sp(2)) H bonds of picolinamide (PA)-protected benzylamine substrates with a broad range of beta-H-containing alkyl halides. Sodium triflate has been identified as a critical promoter for this reaction system. The PA group can be easily installed and removed under mild conditions. This method provides a new strategy to prepare highly functionalized benzylamines for the synthesis of complex molecules.

  DOI：

  10.1021/ol201930e

文献信息

• Palladium-Catalyzed Alkylation of <i>ortho</i>-C(sp²)–H Bonds of Benzylamide Substrates with Alkyl Halides
  作者：Yingsheng Zhao、Gong Chen

  DOI：10.1021/ol201930e

  日期：2011.9.16

  A highly efficient and generally applicable method has been developed to functionalize the ortho-C(sp(2)) H bonds of picolinamide (PA)-protected benzylamine substrates with a broad range of beta-H-containing alkyl halides. Sodium triflate has been identified as a critical promoter for this reaction system. The PA group can be easily installed and removed under mild conditions. This method provides a new strategy to prepare highly functionalized benzylamines for the synthesis of complex molecules.