N-(3-((3-methylbut-2-en-1-yl)oxy)benzyl)picolinamide | 1332481-92-1

• 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-(3-((3-methylbut-2-en-1-yl)oxy)benzyl)picolinamide
• CAS: 1332481-92-1
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: VTTQPQRUPHQSRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(3-((3-methylbut-2-en-1-yl)oxy)benzyl)picolinamide 、 1-碘代丙烷 在 氧气 、 palladium diacetate 、 三氟甲磺酸钠 、 potassium carbonate 作用下， 以 3-甲基-3-戊醇 为溶剂， 135.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 以95%的产率得到N-[[5-(3-methylbut-2-enoxy)-2-propylphenyl]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
• 作为产物：
  描述：

  N-(3-methoxybenzyl)picolinamide 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-(3-((3-methylbut-2-en-1-yl)oxy)benzyl)picolinamide
  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 Alkenylation and Alkynylation of <i>ortho</i>-C(sp²)–H Bonds of Benzylamine Picolinamides
  作者：Yingsheng Zhao、Gang He、William A. Nack、Gong Chen

  DOI：10.1021/ol301214u

  日期：2012.6.15

  An efficient functionalization of ortho-C(sp2)–H bonds of picolinamide (PA)-protected benzylamine substrates with a range of vinyl iodides as well as acetylenic bromide is reported. ortho-Phenyl benzoic acid (oPBA) acts as an effective promoter in this reaction system. This method provides a practical strategy to access highly functionalized benzylamine compounds for organic synthesis.

  据报道，吡啶甲酰胺（PA）保护的苄胺底物的邻位-C（sp 2）-H键与一系列乙烯基碘以及炔属溴化物的有效官能化作用。在该反应体系中，邻苯基苯甲酸（o PBA）充当有效的促进剂。该方法提供了一种实用的策略，可将高度官能化的苄胺化合物用于有机合成。