2-bromo-6-(3-butenylthio)pyridine | 672263-62-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-bromo-6-(3-butenylthio)pyridine
• 英文别名: 2-(3-butenylthio)-6-bromo-pyridine；Pyridine, 2-bromo-6-(3-butenylthio)-；2-bromo-6-but-3-enylsulfanylpyridine
• CAS: 672263-62-6
• 化学式: C₉H₁₀BrNS
• 分子量: 244.155
• InChiKey: NXFJQCOALQUWRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-二溴吡啶 、 二乙烯基硫醚 在 sodium 作用下， 以 氨 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 以52%的产率得到2-bromo-6-vinylthiopyridine
  参考文献：
  名称：

  摘要：

  The use of divinyl sulfide as synthetic equivalent of ethenethiolate and 3-butenethiolate anions makes it possible to obtain vinylthio(halo)- and 3-butenylthio(halo)pyridines from halopyridines. 2,6-Bromo(chloro)pyridines react with a mixture of ethenethiolate and 3-butenethiolate ions more readily than does 3,5-dibromopyridine. The reaction yields mainly products of halogen replacement by vinylthio group. The formation of 3-butenethiolate ion in the reaction of divinyl sulfide with sodium in liquid ammonia is governed by the order of mixing of the reactants. Possible ways of generation of 3-butenethiolate ion in the reaction with 1-bromobutane are discussed.

  DOI：

  10.1023/a:1026025700064

文献信息

• Synthesis of vinylsulfonyl(halo)pyridines and their reactions with binucleophilic reagents
  作者：S. V. Amosova、G. M. Gavrilova

  DOI：10.1007/s11178-005-0075-4

  日期：2004.11

  Oxidation of vinylthio(halo)pyridines with 30–33% hydrogen peroxide solution in acetic anhydride at 20–25°C furnished vinylsulfonyl(halo)pyridines. Nucleophilic addition reactions of 2-amino-1-ethanethio hydrochloride and thiosemicarbazide to the multiple bonds of vinylsulfonyl(halo)pyridines were performed.

  在 20-25°C 的温度下，用 30-33% 的过氧化氢乙酸酐溶液氧化乙烯基硫代（卤代）吡啶，生成了乙烯基磺酰基（卤代）吡啶。2-amino-1-ethanethio hydrochloride 和 thiosemicarbazide 与乙烯砜基（卤代）吡啶的多键发生了亲核加成反应。
• ——
  作者：S. V. Amosova、V. I. Gostevskaya、G. M. Gavrilova、A. V. Afonin

  DOI：10.1023/a:1026025700064

  日期：——

  The use of divinyl sulfide as synthetic equivalent of ethenethiolate and 3-butenethiolate anions makes it possible to obtain vinylthio(halo)- and 3-butenylthio(halo)pyridines from halopyridines. 2,6-Bromo(chloro)pyridines react with a mixture of ethenethiolate and 3-butenethiolate ions more readily than does 3,5-dibromopyridine. The reaction yields mainly products of halogen replacement by vinylthio group. The formation of 3-butenethiolate ion in the reaction of divinyl sulfide with sodium in liquid ammonia is governed by the order of mixing of the reactants. Possible ways of generation of 3-butenethiolate ion in the reaction with 1-bromobutane are discussed.