3-Methyl-4-oxo-4-pyridin-4-yl-butyraldehyde | 224453-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-4-oxo-4-pyridin-4-yl-butyraldehyde
• CAS: 224453-60-5
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: OONCYHASEXRWMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-Methyl-4-oxo-4-pyridin-4-yl-butyraldehyde 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以65%的产率得到4-(3-methylpyrrol-2-yl)pyridine
  参考文献：
  名称：

  Synthesis and MAO-B Substrate Properties of 1-Methyl-4-heteroaryl-1,2,3,6-tetrahydropyridines

  摘要：

  The parkinsonian inducing drug 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is bioactivated in a reaction catalyzed by the flavoenzyme monoamine oxidase B (MAO-B) to form the corresponding dihydropyridinium and subsequently pyridinium metabolites. As part of our ongoing studies to characterize the structural features responsible for this unexpected biotransformation, we have examined the MAO-B substrate properties of a variety of MPTP analogues bearing various heteroaryl groups at the il-position of the tetrahydropyridinyl ring. The newly synthesized analogues are 4-(1-methylimidazol-2-yl)-, 4-(3-methylfuran-2-yl)-, 4-(3-methylthien-2-yl)-, 4-(3,4-dimethylpyrrol-1-yl)-, 4-(3-methylpyrrol-2-yl)-, and 4-(1,3-dimethylpyrrol-2-yl)-1-methyl-1,2,3,6-tetrahydropyridine. Except for the 4-(1-methylimidazol-2-yl) analogue, all compounds displayed good to excellent substrate properties. The 1-methyl-4-(3-methylfuran-2-yl) analogue is the most active member of this series with a k(cat)/K-m value greater than 8,500min(-1)mM(-1). The results of these studies are discussed in terms of catalytic pathways proposed for MAO-B. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00201-6
• 作为产物：
  描述：

  4-吡啶甲醛 、 丁烯-2-醛 在 potassium cyanide 作用下， 生成 3-Methyl-4-oxo-4-pyridin-4-yl-butyraldehyde
  参考文献：
  名称：

  Synthesis and MAO-B Substrate Properties of 1-Methyl-4-heteroaryl-1,2,3,6-tetrahydropyridines

  摘要：

  The parkinsonian inducing drug 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is bioactivated in a reaction catalyzed by the flavoenzyme monoamine oxidase B (MAO-B) to form the corresponding dihydropyridinium and subsequently pyridinium metabolites. As part of our ongoing studies to characterize the structural features responsible for this unexpected biotransformation, we have examined the MAO-B substrate properties of a variety of MPTP analogues bearing various heteroaryl groups at the il-position of the tetrahydropyridinyl ring. The newly synthesized analogues are 4-(1-methylimidazol-2-yl)-, 4-(3-methylfuran-2-yl)-, 4-(3-methylthien-2-yl)-, 4-(3,4-dimethylpyrrol-1-yl)-, 4-(3-methylpyrrol-2-yl)-, and 4-(1,3-dimethylpyrrol-2-yl)-1-methyl-1,2,3,6-tetrahydropyridine. Except for the 4-(1-methylimidazol-2-yl) analogue, all compounds displayed good to excellent substrate properties. The 1-methyl-4-(3-methylfuran-2-yl) analogue is the most active member of this series with a k(cat)/K-m value greater than 8,500min(-1)mM(-1). The results of these studies are discussed in terms of catalytic pathways proposed for MAO-B. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00201-6