6,6'''-bis(ethylthio)-2,2':6',2'':6'',2'''-quaterpyridine | 220400-12-4

• 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: 6,6'''-bis(ethylthio)-2,2':6',2'':6'',2'''-quaterpyridine
• 英文别名: 2-Ethylsulfanyl-6-[6-[6-(6-ethylsulfanylpyridin-2-yl)pyridin-2-yl]pyridin-2-yl]pyridine
• CAS: 220400-12-4
• 化学式: C₂₄H₂₂N₄S₂
• 分子量: 430.597
• InChiKey: UGDMUVRRXAHKHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,6'''-bis(ethylthio)-2,2':6',2'':6'',2'''-quaterpyridine 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 氯仿 为溶剂， 反应 0.25h， 生成 (S)-6-<1-(tert-butyldimethylsiloxy)ethyl>-6''''-ethylthio-2,2':6',2'':6'',2''':6''',2''''-quinqepyridine
  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-ethylsulfinyl-6-ethylthiopyridine 在 甲基溴化镁 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.92h， 生成 6,6'''-bis(ethylthio)-2,2':6',2'':6'',2'''-quaterpyridine
  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.