1-methyl-4-(3-methylphenoxy)pyridinium iodide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-4-(3-methylphenoxy)pyridinium iodide
• 英文别名: 1-methyl-4-m-tolyloxy-pyridinium; iodide；1-Methyl-4-m-tolyloxy-pyridinium; Jodid；1-Methyl-4-(3-methylphenoxy)pyridin-1-ium;iodide
• 化学式: C₁₃H₁₄NO*I
• 分子量: 327.165
• InChiKey: AEHKEAAFZUJYGX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(3-methylphenoxy)pyridinium iodide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-methyl-4-(3-methylphenoxy)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Studies on the Monoamine Oxidase (MAO)-Catalyzed Oxidation of Phenyl-Substituted 1-Methyl-4-phenoxy-1,2,3,6-tetrahydropyridine Derivatives: Factors Contributing to MAO-A and MAO-B Selectivity

  摘要：

  The structural parameters responsible for the substrate and inhibitor selectivities of the monoamine oxidases (MAO) A and B remain poorly understood. This situation has improved somewhat with structure-activity studies that have been performed on nuclear-substituted pargyline derivatives and 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine derivatives. The results of these studies suggest that the active site of MAO-A is sterically more accommodating than the active site of MAO-B. In the present work we have undertaken a more systematic structure-substrate activity analysis with the aid of a series of 4-phenoxytetrahydropyridine analogs substituted at the para, meta, and ortho positions of the phenyl ring with chloro, methoxy, methyl, nitro, and phenyl groups. All of the compounds proved to be good substrates for both MAO-A and MAO-B, and all were better MAO-A substrates than MAO-B substrates. The best defined structural parameter relating to selectivity again was the relative:ly better MAO-A substrate properties of tetrahydropyridine derivatives bearing bulky C-4 substituents. Attempts to identify stereoelectronic effects related to substrate properties and selectivity with this series of compounds were not successful. Although some structural correlates with substrate activity can be made, overall the present state of knowledge is inadequate to provide good descriptors of structural features that characterize MAO-A and MAO-B substrates.

  DOI：

  10.1021/jm00011a010
• 作为产物：
  描述：

  1-(4-吡啶基)吡啶氯盐酸盐 在 乙醚 作用下， 生成 1-methyl-4-(3-methylphenoxy)pyridinium iodide
  参考文献：
  名称：

  Quaternary Derivation of Pyridyl Ethers. Onium Compounds. XVI

  摘要：

  DOI：

  10.1021/ja01281a021

文献信息

• Studies on the Monoamine Oxidase (MAO)-Catalyzed Oxidation of Phenyl-Substituted 1-Methyl-4-phenoxy-1,2,3,6-tetrahydropyridine Derivatives: Factors Contributing to MAO-A and MAO-B Selectivity
  作者：You-Xiong Wang、Neal Castagnoli

  DOI：10.1021/jm00011a010

  日期：1995.5

  The structural parameters responsible for the substrate and inhibitor selectivities of the monoamine oxidases (MAO) A and B remain poorly understood. This situation has improved somewhat with structure-activity studies that have been performed on nuclear-substituted pargyline derivatives and 4-substituted 1-methyl-1,2,3,6-tetrahydropyridine derivatives. The results of these studies suggest that the active site of MAO-A is sterically more accommodating than the active site of MAO-B. In the present work we have undertaken a more systematic structure-substrate activity analysis with the aid of a series of 4-phenoxytetrahydropyridine analogs substituted at the para, meta, and ortho positions of the phenyl ring with chloro, methoxy, methyl, nitro, and phenyl groups. All of the compounds proved to be good substrates for both MAO-A and MAO-B, and all were better MAO-A substrates than MAO-B substrates. The best defined structural parameter relating to selectivity again was the relative:ly better MAO-A substrate properties of tetrahydropyridine derivatives bearing bulky C-4 substituents. Attempts to identify stereoelectronic effects related to substrate properties and selectivity with this series of compounds were not successful. Although some structural correlates with substrate activity can be made, overall the present state of knowledge is inadequate to provide good descriptors of structural features that characterize MAO-A and MAO-B substrates.
• Quaternary Derivation of Pyridyl Ethers. Onium Compounds. XVI
  作者：R. R. Renshaw、R. C. Conn

  DOI：10.1021/ja01281a021

  日期：1937.2