2,6-二(乙硫基)吡啶 | 120716-68-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2,6-二(乙硫基)吡啶
• 英文名称: 2,6-bis(ethylthio)pyridine
• 英文别名: 2,6-Bis(ethylsulfanyl)pyridine
• CAS: 120716-68-9
• 化学式: C₉H₁₃NS₂
• 分子量: 199.341
• InChiKey: NIKBUTMQFWPEKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二(乙硫基)吡啶 在 甲基溴化镁 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.34h， 生成 6-(乙硫基)-2,2'-联吡啶
  参考文献：
  名称：

  Coupling of Consecutive Pyridine Ring Units for Oligopyridine Synthesis

  摘要：

  The reaction of 2-ethylsulfinyl-6-(ethylthio)pyridine (2), 6-ethylsulfinyl-6'-ethylthio-2,2'- -bipyridine (6), and 6-ethylsulfinyl-6"'-ethylthio-2,2':6',2 ":6 ",2'''-quaterpyridine (10) with methylmagnesium bromide gave symmetric oligopyridines 6,6'-bis(ethylthio)-2,2'-bipyridine (4), 6,6'''-bis(ethylthio)-2,2':6',2 ":6 ",2'''-quaterpyridine (8), and 6,6'''''''-bis(ethylthio)-2,2':6',2 ":6 ",2''':6''',2'''':6'''',2''''':6''''',2'''''':6'''''',2'''''''-octipyridine (12) in respective yields of 70, 56, and 3%. On the other hand, the reaction of 6 and 10 with 2-(6-bromopyridinyl) lithium and 6-(2,2'-bipyridinyl)lithium gave the corresponding unsymmetric oligopyridines (15, 16, 13, and 19). The reaction with chiral (S)-2-{6-[1-(tert-butyldimethylsiloxy)-ethyl]pyridinyl}lithium gave optically active oligopyridines (17) and (18) in 78 and 58% yields, respectively.

  DOI：

  10.3987/com-98-s(h)57
• 作为产物：
  描述：

  2,6-二氯吡啶 、 乙硫醇钠 在 sodium hydride 作用下， 以 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以96%的产率得到2,6-二(乙硫基)吡啶
  参考文献：
  名称：

  Coupling of Consecutive Pyridine Ring Units for Oligopyridine Synthesis

  摘要：

  The reaction of 2-ethylsulfinyl-6-(ethylthio)pyridine (2), 6-ethylsulfinyl-6'-ethylthio-2,2'- -bipyridine (6), and 6-ethylsulfinyl-6"'-ethylthio-2,2':6',2 ":6 ",2'''-quaterpyridine (10) with methylmagnesium bromide gave symmetric oligopyridines 6,6'-bis(ethylthio)-2,2'-bipyridine (4), 6,6'''-bis(ethylthio)-2,2':6',2 ":6 ",2'''-quaterpyridine (8), and 6,6'''''''-bis(ethylthio)-2,2':6',2 ":6 ",2''':6''',2'''':6'''',2''''':6''''',2'''''':6'''''',2'''''''-octipyridine (12) in respective yields of 70, 56, and 3%. On the other hand, the reaction of 6 and 10 with 2-(6-bromopyridinyl) lithium and 6-(2,2'-bipyridinyl)lithium gave the corresponding unsymmetric oligopyridines (15, 16, 13, and 19). The reaction with chiral (S)-2-{6-[1-(tert-butyldimethylsiloxy)-ethyl]pyridinyl}lithium gave optically active oligopyridines (17) and (18) in 78 and 58% yields, respectively.

  DOI：

  10.3987/com-98-s(h)57

文献信息

• Coupling of Consecutive Pyridine Ring Units for Oligopyridine Synthesis
  作者：Jun'ichi Uenishi、Tetsuya Ueno、Sin'ichiro Hata、Kenji Nishiwaki、Takakazu Tanaka、Shoji Wakabayashi、Osamu Yonemitsu、Shigeru Oae

  DOI：10.3987/com-98-s(h)57

  日期：——

  The reaction of 2-ethylsulfinyl-6-(ethylthio)pyridine (2), 6-ethylsulfinyl-6'-ethylthio-2,2'- -bipyridine (6), and 6-ethylsulfinyl-6"'-ethylthio-2,2':6',2 ":6 ",2'''-quaterpyridine (10) with methylmagnesium bromide gave symmetric oligopyridines 6,6'-bis(ethylthio)-2,2'-bipyridine (4), 6,6'''-bis(ethylthio)-2,2':6',2 ":6 ",2'''-quaterpyridine (8), and 6,6'''''''-bis(ethylthio)-2,2':6',2 ":6 ",2''':6''',2'''':6'''',2''''':6''''',2'''''':6'''''',2'''''''-octipyridine (12) in respective yields of 70, 56, and 3%. On the other hand, the reaction of 6 and 10 with 2-(6-bromopyridinyl) lithium and 6-(2,2'-bipyridinyl)lithium gave the corresponding unsymmetric oligopyridines (15, 16, 13, and 19). The reaction with chiral (S)-2-6-[1-(tert-butyldimethylsiloxy)-ethyl]pyridinyl}lithium gave optically active oligopyridines (17) and (18) in 78 and 58% yields, respectively.