4-methoxy-5-(4-methoxyphenyl)-1-methyl-3-(trimethylsilylethynyl)pyridin-2(1H)-one | 925901-05-9

• 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: 4-methoxy-5-(4-methoxyphenyl)-1-methyl-3-(trimethylsilylethynyl)pyridin-2(1H)-one
• 英文别名: 4-Methoxy-5-(4-methoxyphenyl)-1-methyl-3-(2-trimethylsilylethynyl)pyridin-2-one；4-methoxy-5-(4-methoxyphenyl)-1-methyl-3-(2-trimethylsilylethynyl)pyridin-2-one
• CAS: 925901-05-9
• 化学式: C₁₉H₂₃NO₃Si
• 分子量: 341.482
• InChiKey: ZIVSJBGMJOVEEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-5-(4-methoxyphenyl)-1-methyl-3-(trimethylsilylethynyl)pyridin-2(1H)-one 在 三氟乙酸 作用下， 反应 16.0h， 以72%的产率得到3-acetyl-4-methoxy-5-(4-methoxyphenyl)-1-methylpyridin-2(1H)-one
  参考文献：
  名称：

  Flexible Strategy for Differentially 3,5-Disubstituted 4-Oxypyridin-2(1H)-ones Based on Site-Selective Pd-Catalyzed Cross-Coupling Reactions

  摘要：

  3,5-Dihalogeno-4-methoxy-N-methylpyridin-2(1H)-ones have been shown to undergo single Suzuki coupling reactions in a site-selective fashion. Monoarylations occur at the C-5 position preferentially, thus leaving the remaining C-3 halide free for further functionalization, to finally access differentially 3,5-disubstituted 2-pyridones. This two-step strategy has been applied to the elaboration of the 3-acyl-5-aryl-4-oxy-2-pyridone subunit that is prevalent in numerous bioactive natural products.

  DOI：

  10.1021/ol062721u
• 作为产物：
  描述：

  4-甲氧基-1-甲基吡啶-2-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate N-碘代丁二酰亚胺 、 copper(l) iodide 、 trisodium tris(3-sulfophenyl)phosphine 、 三乙胺 、 二异丙胺 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 67.0h， 生成 4-methoxy-5-(4-methoxyphenyl)-1-methyl-3-(trimethylsilylethynyl)pyridin-2(1H)-one
  参考文献：
  名称：

  Flexible Strategy for Differentially 3,5-Disubstituted 4-Oxypyridin-2(1H)-ones Based on Site-Selective Pd-Catalyzed Cross-Coupling Reactions

  摘要：

  3,5-Dihalogeno-4-methoxy-N-methylpyridin-2(1H)-ones have been shown to undergo single Suzuki coupling reactions in a site-selective fashion. Monoarylations occur at the C-5 position preferentially, thus leaving the remaining C-3 halide free for further functionalization, to finally access differentially 3,5-disubstituted 2-pyridones. This two-step strategy has been applied to the elaboration of the 3-acyl-5-aryl-4-oxy-2-pyridone subunit that is prevalent in numerous bioactive natural products.

  DOI：

  10.1021/ol062721u

文献信息

• Et₃N-Induced Demethylation−Annulation of 3-Alkynyl-4-methoxy-2-pyridones and Structurally Related Compounds in the Synthesis of Furan-Fused Heterocycles
  作者：David Conreaux、Sébastien Belot、Philippe Desbordes、Nuno Monteiro、Geneviève Balme

  DOI：10.1021/jo8014038

  日期：2008.11.7

  Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling. dealkylation, and regioselective furan annulation reactions. A Et3N-induced S(N)2 process has been established that accounts for the dealkylation process.
• Flexible Strategy for Differentially 3,5-Disubstituted 4-Oxypyridin-2(1<i>H</i>)-ones Based on Site-Selective Pd-Catalyzed Cross-Coupling Reactions
  作者：David Conreaux、Emmanuel Bossharth、Nuno Monteiro、Philippe Desbordes、Jean-Pierre Vors、Geneviève Balme

  DOI：10.1021/ol062721u

  日期：2007.1.1

  3,5-Dihalogeno-4-methoxy-N-methylpyridin-2(1H)-ones have been shown to undergo single Suzuki coupling reactions in a site-selective fashion. Monoarylations occur at the C-5 position preferentially, thus leaving the remaining C-3 halide free for further functionalization, to finally access differentially 3,5-disubstituted 2-pyridones. This two-step strategy has been applied to the elaboration of the 3-acyl-5-aryl-4-oxy-2-pyridone subunit that is prevalent in numerous bioactive natural products.