5-溴-n-环己基-3-甲基吡啶甲酰胺 | 244139-63-7

• 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: 5-溴-n-环己基-3-甲基吡啶甲酰胺
• 英文名称: 5-Bromo-3-methyl-N-cyclohexylpyridine-2-carboxamide
• 英文别名: 5-bromo-N-cyclohexyl-3-methylpyridine-2-carboxamide
• CAS: 244139-63-7
• 化学式: C₁₃H₁₇BrN₂O
• 分子量: 297.195
• InChiKey: DTIMPNAZTFUAIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二溴-3-甲基吡啶 、 一氧化碳 、 环己胺 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 55.0 ℃ 、689.49 kPa 条件下， 反应 6.0h， 以64%的产率得到5-溴-n-环己基-3-甲基吡啶甲酰胺
  参考文献：
  名称：

  Novel 2,2-Bipyridine Ligand for Palladium-Catalyzed Regioselective Carbonylation

  摘要：

  [GRAPHICS]A palladium-catalyzed highly regioselective one-step carbonylation of 2,5-dibromo 3-methylpyridine is reported. A range of alkyl esters and amides can be prepared in good yield with better than 95:5 regioselectivity via this method. Key to the high regioselectivity for the formation aromatic amides is the introduction of a novel nonphosphine based 2,2 bipyridine ligand, This novel reaction was scaled up smoothly in the plant to a 130-kg batch size and facilitated the delivery of bulk material for the clinical trials of Sch 66336, a candidate for oncologic treatments.

  DOI：

  10.1021/ol990123s

文献信息

• Novel 2,2-Bipyridine Ligand for Palladium-Catalyzed Regioselective Carbonylation
  作者：George Guangzhong Wu、YeeShing Wong、Marc Poirier

  DOI：10.1021/ol990123s

  日期：1999.9.1

  [GRAPHICS]A palladium-catalyzed highly regioselective one-step carbonylation of 2,5-dibromo 3-methylpyridine is reported. A range of alkyl esters and amides can be prepared in good yield with better than 95:5 regioselectivity via this method. Key to the high regioselectivity for the formation aromatic amides is the introduction of a novel nonphosphine based 2,2 bipyridine ligand, This novel reaction was scaled up smoothly in the plant to a 130-kg batch size and facilitated the delivery of bulk material for the clinical trials of Sch 66336, a candidate for oncologic treatments.