2-acetoxy-1-methyl-5-(3-pyridyl)pyrrole | 230308-26-6

• 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: 2-acetoxy-1-methyl-5-(3-pyridyl)pyrrole
• 英文别名: (1-methyl-5-pyridin-3-ylpyrrol-2-yl) acetate
• CAS: 230308-26-6
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: NNBLXDUSGPXBMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-acetoxy-1-methyl-5-(3-pyridyl)pyrrole 在 diclazuril 作用下， 以 重水 为溶剂， 反应 1.17h， 生成 5-hydroxycotinine
  参考文献：
  名称：

  Studies on the Pyrrolinone Metabolites Derived from the Tobacco Alkaloid 1-Methyl-2-(3-pyridinyl)pyrrole (β-Nicotyrine)

  摘要：

  Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (beta-nicotyrine) is biotransformed by rabbit lung and liver microsomal preparations to an equilibrium mixture of the corresponding 3- and 4-pyrrolin-2-ones. Autoxidation of these pyrrolin-2-ones generates the chemically stable 5-hydroxy-5-(3-pyridinyl)-3-pyrrolin-2-one. This paper summarizes efforts to document more completely the pathway leading to this hydroxy-pyrrolinone. Chemical and spectroscopic evidence implicates the 2-hydroxy-1-methyl-5-(3-pyridinyl)pyrrole (2-hydroxy-beta-nicotyrine) as the key intermediate in this reaction pathway. Of potential toxicological interest is the detection of radical species derived from the autoxidation of this compound.

  DOI：

  10.1021/tx990019j
• 作为产物：
  描述：

  (R,S)-1-methyl-5-(3'-pyridyl)-5-methoxypyrrolin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0~80.0 ℃ 、98.06 kPa 条件下， 反应 30.0h， 生成 2-acetoxy-1-methyl-5-(3-pyridyl)pyrrole
  参考文献：
  名称：

  Studies on the Pyrrolinone Metabolites Derived from the Tobacco Alkaloid 1-Methyl-2-(3-pyridinyl)pyrrole (β-Nicotyrine)

  摘要：

  Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (beta-nicotyrine) is biotransformed by rabbit lung and liver microsomal preparations to an equilibrium mixture of the corresponding 3- and 4-pyrrolin-2-ones. Autoxidation of these pyrrolin-2-ones generates the chemically stable 5-hydroxy-5-(3-pyridinyl)-3-pyrrolin-2-one. This paper summarizes efforts to document more completely the pathway leading to this hydroxy-pyrrolinone. Chemical and spectroscopic evidence implicates the 2-hydroxy-1-methyl-5-(3-pyridinyl)pyrrole (2-hydroxy-beta-nicotyrine) as the key intermediate in this reaction pathway. Of potential toxicological interest is the detection of radical species derived from the autoxidation of this compound.

  DOI：

  10.1021/tx990019j

文献信息

• Studies on the Pyrrolinone Metabolites Derived from the Tobacco Alkaloid 1-Methyl-2-(3-pyridinyl)pyrrole (β-Nicotyrine)
  作者：Xin Liu、Lunyi Zang、Cornelis J. Van der Schyf、Kazuo Igarashi、Kay Castagnoli、Neal Castagnoli

  DOI：10.1021/tx990019j

  日期：1999.6.1

  Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (beta-nicotyrine) is biotransformed by rabbit lung and liver microsomal preparations to an equilibrium mixture of the corresponding 3- and 4-pyrrolin-2-ones. Autoxidation of these pyrrolin-2-ones generates the chemically stable 5-hydroxy-5-(3-pyridinyl)-3-pyrrolin-2-one. This paper summarizes efforts to document more completely the pathway leading to this hydroxy-pyrrolinone. Chemical and spectroscopic evidence implicates the 2-hydroxy-1-methyl-5-(3-pyridinyl)pyrrole (2-hydroxy-beta-nicotyrine) as the key intermediate in this reaction pathway. Of potential toxicological interest is the detection of radical species derived from the autoxidation of this compound.