6,6'-bis(ethylsulfanyl)-2,2'-bipyridine | 130897-03-9

• 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(ethylsulfanyl)-2,2'-bipyridine
• 英文别名: 6,6'-bis(ethylthio)-2,2'-bipyridine；2,2'-Bis(ethylsulfanyl)-6,6'-bipyridine；2-ethylsulfanyl-6-(6-ethylsulfanylpyridin-2-yl)pyridine
• CAS: 130897-03-9
• 化学式: C₁₄H₁₆N₂S₂
• 分子量: 276.426
• InChiKey: IKCVPFLRAFEXCS-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  442.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6'-bis(ethylsulfanyl)-2,2'-bipyridine 在 甲基溴化镁 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.67h， 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-ethylsulfinyl-6-ethylthiopyridine 在 甲基溴化镁 作用下， 以 乙醚 为溶剂， 以60%的产率得到6,6'-bis(ethylsulfanyl)-2,2'-bipyridine
  参考文献：
  名称：

  2-烷基亚磺酰基吡啶被2-吡啶基锂的异丙基取代；寡吡啶及其溴甲基衍生物的新制备方法

  摘要：

  已经制备了不对称和对称的2,2'-联吡啶5和6。所应用的方法是新方法，可提供高级寡吡啶及其溴代甲基衍生物的有效合成方法。

  DOI：

  10.1016/s0040-4039(00)97692-5

文献信息

• The first approach to optically active 2,2′-bipyridine alkyl sulfoxides
  作者：Justyna Ławecka、Bogdan Bujnicki、Józef Drabowicz、Andrzej Rykowski

  DOI：10.1016/j.tetlet.2007.11.104

  日期：2008.1

  The synthesis of 6,6′-bis(alkylsulfanyl)-2,2′-bipyridines and their asymmetric oxidation to non-racemic 2,2′-bipyridine alkyl sulfoxides using either (+)-(8,8-dichlorocamphorylsulfonyl)oxaziridine or a modified Sharpless reagent is reported.

  6,6'-双（烷基硫烷基）-2,2'-联吡啶的合成及其使用（+）-（8,8-二氯樟脑磺酰基磺酰基）恶唑烷或不对称氧化为非外消旋的2,2'-联吡啶烷基亚砜报道了一种改良的Sharpless试剂。
• Synthesis of Enantiomerically Enriched Mono and Bis 2,2′-Bipyridine Alkyl Sulfoxides and Their First Application as Chiral Auxiliaries
  作者：Justyna Ławecka、Bogdan Bujnicki、Józef Drabowicz、Jerzy Łuczak、Andrzej Rykowski

  DOI：10.1080/10426500902856347

  日期：2009.5.14

  The direct asymmetric oxidation of 6,6'-bis(alkylsulfanyl)-2,2'-bipyridines 2a-e to non-racemic mono sulfoxides 3a-e and bis-sulfoxides 4a,c-e using either Davis oxaziridine or a modified Sharples reagent is reported. The use of isolated mono- and bis-sulfoxides as chiral auxiliaries was tested in either the asymmetric addition of the diethylzinc or allyl(trichloro)silane to benzaldehyde.
• UENISHI, JUNICHI;TANAKA, TAKAKAZU;WAKABAYASHI, SHOJI, TETRAHEDRON LETT., 31,(1990) N2, C. 4625-4628
  作者：UENISHI, JUNICHI、TANAKA, TAKAKAZU、WAKABAYASHI, SHOJI

  DOI：——

  日期：——
• 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.
• Ipso substitution of 2-alkylsulfinylpyridine by 2-pyridyllithium; a new preparation of oligopyridine and their bromomethyl derivatives
  作者：Junichi Uenishi、Takakazu Tanaka、Shoji Wakabayashi、Shigeru Oae、Hiroshi Tsukube

  DOI：10.1016/s0040-4039(00)97692-5

  日期：1990.1

  Unsymmetrical and symmetrical 2,2′-bipyridines 5 and 6 have been prepared. The methods applied are new and offer efficient syntheses of higher oligopyridines and their bromomethyl derivatives.

  已经制备了不对称和对称的2,2'-联吡啶5和6。所应用的方法是新方法，可提供高级寡吡啶及其溴代甲基衍生物的有效合成方法。