6-(乙硫基)-2,2'-联吡啶 | 130897-01-7

• 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
• 中文名称: 6-(乙硫基)-2,2'-联吡啶
• 英文名称: 6-ethylthio-2,2'-bipyridine
• 英文别名: 2-ethylsulfanyl-6-pyridin-2-ylpyridine
• CAS: 130897-01-7
• 化学式: C₁₂H₁₂N₂S
• 分子量: 216.307
• InChiKey: PYTAHXAHIXLUCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(乙硫基)-2,2'-联吡啶 在 正丁基锂 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 生成 α,α,α-三联吡啶
  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
• 作为产物：
  描述：

  ethyl 2-pyridyl sulfoxide 在 正丁基锂 、 sodium hydride 作用下， 反应 0.42h， 生成 6-(乙硫基)-2,2'-联吡啶
  参考文献：
  名称：

  Synthesis of ι-(bromomethyl)bipyridines and related ι-(bromomethyl)pyridinoheteroaromatics: useful functional tools for ligands in host molecules

  摘要：

  Pyridines and 2,2'-bipyridines have been employed as useful ligands in molecular recognition chemistries. Halomethyl-substituted bipyridine or oligopyridine derivatives were required for the assembly of bipyridine or oligopyridine units with a supporting mother functional part in artificial biofunctional molecules. A series of omega-(bromomethyl)bipyridines and related omega-(bromomethyl)pyridinoheteroaromatic compounds (types I-III) were synthesized in this paper. Preparation of oligopyridines and pyridinoheteroaromatic compounds have been carried out by either intermolecular ligand coupling of alkyl heteroaryl sulfoxide with pyridyllithium or intramolecular ligand coupling of pyridyl heteroaryl sulfoxide with methylmagnesium bromide for the type I compounds. The type II and III compounds were synthesized by addition of pyridyllithium to pyridinecarboxaldehyde. The omega-bromo group was introduced by radical bromination reaction of methylpyridyl group using NBS and BPO (dibenzoyl peroxide) or bromination of omega-(hydroxymethyl)pyridine using a combination of CBr4 and Ph3P.

  DOI：

  10.1021/jo00068a037

文献信息

• [Cu(P^P)(N^N)][PF₆] compounds with bis(phosphane) and 6-alkoxy, 6-alkylthio, 6-phenyloxy and 6-phenylthio-substituted 2,2′-bipyridine ligands for light-emitting electrochemical cells
  作者：Murat Alkan-Zambada、Sarah Keller、Laura Martínez-Sarti、Alessandro Prescimone、José M. Junquera-Hernández、Edwin C. Constable、Henk J. Bolink、Michele Sessolo、Enrique Ortí、Catherine E. Housecroft

  DOI：10.1039/c8tc02882f

  日期：——

  We report a series of [Cu(P^P)(N^N)][PF6] complexes with P^P = bis(2-(diphenylphosphino)phenyl)ether (POP) or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) and N^N = 6-methoxy-2,2′-bipyridine (MeObpy), 6-ethoxy-2,2′-bipyridine (EtObpy), 6-phenyloxy-2,2′-bipyridine (PhObpy), 6-methylthio-2,2′-bipyridine (MeSbpy), 6-ethylthio-2,2′-bipyridine (EtSbpy) and 6-phenylthio-2,2′-bipyridine (PhSbpy)

  我们报道了一系列[Cu（P ^ P）（N ^ N）] [PF 6 ]配合物，其中P ^ P =双（2-（二苯基膦基）苯基）醚（POP）或4,5-双（二苯基膦基） -9,9-二甲基x吨（xantphos）和N ^ N = 6-甲氧基-2,2'-联吡啶（MeObpy），6-乙氧基-2,2'-联吡啶（EtObpy），6-苯氧基-2,2' -联吡啶（PhObpy），6-甲硫基2,2'-联吡啶（MeSbpy），6-乙硫基2,2'-联吡啶（EtSbpy）和6-苯硫基-2,2'-联吡啶（PhSbpy）。已确定所有十二种化合物的单晶结构，并确定了每个N ^ N和P ^ P配体的螯合模式，以及铜（I）的扭曲的四面体几何形状。对于含黄磷的配合物，不对称的bpy配体排列成6位取代基位于the吨的“碗”上。这些化合物在溶液中的特征是1描述了H，13 C和31 P NMR光谱，及其光物理和电化学性质。它们是黄色发射
• 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.
• 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：——
• Synthesis of ι-(bromomethyl)bipyridines and related ι-(bromomethyl)pyridinoheteroaromatics: useful functional tools for ligands in host molecules
  作者：Junichi Uenishi、Takakazu Tanaka、Kenji Nishiwaki、Shoji Wakabayashi、Shigeru Oae、Hiroshi Tsukube

  DOI：10.1021/jo00068a037

  日期：1993.7

  Pyridines and 2,2'-bipyridines have been employed as useful ligands in molecular recognition chemistries. Halomethyl-substituted bipyridine or oligopyridine derivatives were required for the assembly of bipyridine or oligopyridine units with a supporting mother functional part in artificial biofunctional molecules. A series of omega-(bromomethyl)bipyridines and related omega-(bromomethyl)pyridinoheteroaromatic compounds (types I-III) were synthesized in this paper. Preparation of oligopyridines and pyridinoheteroaromatic compounds have been carried out by either intermolecular ligand coupling of alkyl heteroaryl sulfoxide with pyridyllithium or intramolecular ligand coupling of pyridyl heteroaryl sulfoxide with methylmagnesium bromide for the type I compounds. The type II and III compounds were synthesized by addition of pyridyllithium to pyridinecarboxaldehyde. The omega-bromo group was introduced by radical bromination reaction of methylpyridyl group using NBS and BPO (dibenzoyl peroxide) or bromination of omega-(hydroxymethyl)pyridine using a combination of CBr4 and Ph3P.
• 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。