3-溴-5-碘-4-甲氧基-1-甲基吡啶-2-酮 | 920490-71-7

• 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
• 中文名称: 3-溴-5-碘-4-甲氧基-1-甲基吡啶-2-酮
• 英文名称: 3-bromo-5-iodo-4-methoxy-1-methylpyridin-2(1H)-one
• 英文别名: 3-bromo-5-iodo-4-methoxy-1-methylpyridin-2-one
• CAS: 920490-71-7
• 化学式: C₇H₇BrINO₂
• 分子量: 343.947
• InChiKey: NAXHAOUKKXHJAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335

反应信息

• 作为反应物：
  描述：

  3-溴-5-碘-4-甲氧基-1-甲基吡啶-2-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 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 32.0h， 生成 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 N-碘代丁二酰亚胺 、 溴 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 3-溴-5-碘-4-甲氧基-1-甲基吡啶-2-酮
  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

• [EN] DIHALOGENATION OF N,O-DISUBSTITUTED HYDROXIPYRIDONES AND USES THEREOF<br/>[FR] DIHALOGENATION D'HYDROXIPYRIDONES N,O-DISUBSTITUEES ET LEURS UTILISATIONS
  申请人：BAYER CROPSCIENCE SA

  公开号：WO2007006591A2

  公开（公告）日：2007-01-18

  [EN] The invention concerns a method for preparing N, O-disubstituted 3,5-dihalogeno-4-hydroxypyridin-2(1H)one. Said compounds may be symmetrical and are particularly useful for synthesis of compounds with agrochemical or pharmaceutical activity.
  [FR] Procédé pour la préparation de 3,5-dihalogéno-4-hydroxypyridin-2(1H)-one N,O-disubstituées. Ces composés peuvent être symétriques ou non symétriques et sont notamment utiles pour la synthèse de composés à activité agrochimique ou pharmaceutique.
• 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.