4-Methoxy-2-[(3-methylphenyl)methyl]pyridine | 1052101-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Methoxy-2-[(3-methylphenyl)methyl]pyridine
• CAS: 1052101-58-2
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: UXPUKWNIEJRCFC-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：
  0.21
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Methoxy-2-[(3-methylphenyl)methyl]pyridine 、 palladium diacetate 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Insights into Directing Group Ability in Palladium-Catalyzed C−H Bond Functionalization

  摘要：

  This paper describes a detailed investigation of factors controlling the dominance of a directing group in Pd-catalyzed ligand-directed arene acetoxylation. Mechanistic studies, involving reaction kinetics, Hammett analysis, kinetic isotope effect experiments, and the kinetic order in oxidant, have been conducted for a series of different substrates. Initial rates studies of substrates bearing different directing groups showed that these transformations are accelerated by the use of electron-withdrawing directing groups. However, in contrast, under conditions where two directing groups are in competition with one another in the same reaction flask, substrates with electron-donating directing groups react preferentially. These results are discussed in the context of the proposed mechanism for Pd-catalyzed arene acetoxylation.

  DOI：

  10.1021/ja8045519
• 作为产物：
  描述：

  bromozinc(1+),1-methanidyl-3-methylbenzene 、 2-氯-4-甲氧基吡啶 在 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 为溶剂， 生成 4-Methoxy-2-[(3-methylphenyl)methyl]pyridine
  参考文献：
  名称：

  Insights into Directing Group Ability in Palladium-Catalyzed C−H Bond Functionalization

  摘要：

  This paper describes a detailed investigation of factors controlling the dominance of a directing group in Pd-catalyzed ligand-directed arene acetoxylation. Mechanistic studies, involving reaction kinetics, Hammett analysis, kinetic isotope effect experiments, and the kinetic order in oxidant, have been conducted for a series of different substrates. Initial rates studies of substrates bearing different directing groups showed that these transformations are accelerated by the use of electron-withdrawing directing groups. However, in contrast, under conditions where two directing groups are in competition with one another in the same reaction flask, substrates with electron-donating directing groups react preferentially. These results are discussed in the context of the proposed mechanism for Pd-catalyzed arene acetoxylation.

  DOI：

  10.1021/ja8045519