3-bromo-5-(vinylthio)-pyridine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-bromo-5-(vinylthio)-pyridine
• 英文别名: 3-bromo-5-vinylthiopyridine；3-bromo-5-ethenylsulfanylpyridine
• 化学式: C₇H₆BrNS
• 分子量: 216.101
• InChiKey: IDGASILERFBYQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3,5-二溴吡啶 、 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 15.0h， 以33%的产率得到3-bromo-5-(vinylthio)-pyridine
  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

• Amosova, S. V.; Gostevskaya, V. I.; Gavrilova, G. M., Russian Journal of Organic Chemistry, 1993, vol. 29, # 7.2, p. 1252 - 1254
  作者：Amosova, S. V.、Gostevskaya, V. I.、Gavrilova, G. M.、Afonin, A. V.

  DOI：——

  日期：——
• ——
  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.