2-bromo-3-(methoxymethoxy)-6-methylpyridine

• 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: 2-bromo-3-(methoxymethoxy)-6-methylpyridine
• 英文别名: 2-Bromo-3-(methoxymethoxy)-6-methylpyridine
• 化学式: C₈H₁₀BrNO₂
• 分子量: 232.077
• InChiKey: OOYRSRJFUANLHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 2-bromo-3-(methoxymethoxy)-6-methylpyridine 在 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium acetate 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 5.0h， 以253 mg的产率得到(E)-methyl 3-(3-(methoxymethoxy)-6-methylpyridin-2-yl)acrylate
  参考文献：
  名称：

  Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone

  摘要：

  Heck vinylation of 2-bromo-6-methyl-3-substituted pyridines using eta(3)-allylpalladium chloride dimer/P(o-Tol)(3) complex/toluene and dimethylacetamide (DMA) as co-solvent with methyl acrylate is reported. Electronic and steric effects were investigated engaging diversely 2-bromo-3,6-disubstituted pyridines. As application, a new synthesis of the 6-methyl cyclopenta[b]pyridinone building-block connecting Heck vinylation, alkene reduction and Dieckmann condensation is described. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.03.008
• 作为产物：
  描述：

  3-羟基-6-甲基吡啶 在 吡啶 、 溴 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 2-bromo-3-(methoxymethoxy)-6-methylpyridine
  参考文献：
  名称：

  Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone

  摘要：

  Heck vinylation of 2-bromo-6-methyl-3-substituted pyridines using eta(3)-allylpalladium chloride dimer/P(o-Tol)(3) complex/toluene and dimethylacetamide (DMA) as co-solvent with methyl acrylate is reported. Electronic and steric effects were investigated engaging diversely 2-bromo-3,6-disubstituted pyridines. As application, a new synthesis of the 6-methyl cyclopenta[b]pyridinone building-block connecting Heck vinylation, alkene reduction and Dieckmann condensation is described. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2005.03.008

文献信息

• Efficient and fast Heck vinylation of 2-bromo-6-methyl pyridines with methylacrylate. Application to the synthesis of 6-methyl cyclopenta[b]pyridinone
  作者：Nicolas Robert、Christophe Hoarau、Sylvain Célanire、Pierre Ribéreau、Alain Godard、Guy Quéguiner、Francis Marsais

  DOI：10.1016/j.tet.2005.03.008

  日期：2005.5

  Heck vinylation of 2-bromo-6-methyl-3-substituted pyridines using eta(3)-allylpalladium chloride dimer/P(o-Tol)(3) complex/toluene and dimethylacetamide (DMA) as co-solvent with methyl acrylate is reported. Electronic and steric effects were investigated engaging diversely 2-bromo-3,6-disubstituted pyridines. As application, a new synthesis of the 6-methyl cyclopenta[b]pyridinone building-block connecting Heck vinylation, alkene reduction and Dieckmann condensation is described. (c) 2005 Published by Elsevier Ltd.