3-carbethoxy-1-(cyanomethyl)-6-(2-bromophenyl)-4(1H)-pyridinone | 134653-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-carbethoxy-1-(cyanomethyl)-6-(2-bromophenyl)-4(1H)-pyridinone
• 英文别名: ethyl 6-(2-bromophenyl)-1-(cyanomethyl)-4-oxopyridine-3-carboxylate
• CAS: 134653-97-7
• 化学式: C₁₆H₁₃BrN₂O₃
• 分子量: 361.195
• InChiKey: FOSYSLJLYJBCQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.09
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate 在 盐酸 、 正丁基锂 、 sodium acetate 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 2.75h， 生成 3-carbethoxy-1-(cyanomethyl)-6-(2-bromophenyl)-4(1H)-pyridinone
  参考文献：
  名称：

  Generation and in situ acylation of enaminone anions: a convenient synthesis of 3-carbethoxy-4(1H)-pyridinones and -4-pyrones and related compounds

  摘要：

  Treatment of 2-[(dimethylamino)methylene]-3-oxobutanoates 9 or 10 with LiN(SiMe3)2 in the presence of RCOCl results in C-acylation. The resulting intermediate, without isolation, may be converted to 6-R 3-Carbethoxy-4-pyrones (e.g., 12) by H3O+ or to the corresponding pyridinones (e.g., 13) by NH4OAc. Typically, yields are 55-75% for R groups lacking acidic alpha or gamma protons and ca. 30% for R = Me2CH or MeCH = CH. Replacing 9 with MeCOC(= CHNMe2)SCH2Ph (from MeCOCH2SCH2Ph and Me2NCH(OMe)2 similarly affords 3(PhCH2S)-substituted products such as 29. Alkylation of the pyridinone anions produces mixtures of N- and O-substituted compounds, with the latter predominating; aminolysis of the isolated pyrones (R'NH2-HOAc, where R' = alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones.

  DOI：

  10.1021/jo00016a028