5-(methoxycarbonyl)-3-methyl-2-pyridone | 66909-31-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 5-(methoxycarbonyl)-3-methyl-2-pyridone
• 英文别名: Methyl 6-hydroxy-5-methylpyridine-3-carboxylate；methyl 5-methyl-6-oxo-1H-pyridine-3-carboxylate
• CAS: 66909-31-7
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: SANWLADGJPSXJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  isopropyl N-((Z)-1-((tert-butyldimethylsilyl)oxy)prop-1-en-1-yl)formimidate 、 丙炔酸甲酯 以 氯仿 为溶剂， 反应 7.0h， 以50%的产率得到5-(methoxycarbonyl)-3-methyl-2-pyridone
  参考文献：
  名称：

  A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy

  摘要：

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01149-1

文献信息

• WEGLINSKI Z.; TALIK T., ROCZ. CHEM. <ROCH-AC>, 1977, 51, NO 12, 2401-2409
  作者：WEGLINSKI Z.、 TALIK T.

  DOI：——

  日期：——
• A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy
  作者：Lon Ghosez、Eric Jnoff、Philippe Bayard、Francy Sainte、Renaud Beaudegnies

  DOI：10.1016/s0040-4020(98)01149-1

  日期：1999.3

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.