6-(乙基亚磺酰)-2,2'-联吡啶 | 149775-39-3

• 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-(乙基亚磺酰)-2,2'-联吡啶
• 英文名称: Ethyl 6-(2,2'-pyridyl) sulfoxide
• 英文别名: 6-Ethylsulfinyl-2,2'-bipyridine；2-ethylsulfinyl-6-pyridin-2-ylpyridine
• CAS: 149775-39-3
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: SOTBPMMJNICFER-UHFFFAOYSA-N

物化性质

• 沸点：
  452.7±35.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 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：
  62.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(乙基亚磺酰)-2,2'-联吡啶 在 正丁基锂 作用下， 反应 0.17h， 生成 6-(6-吡啶-2-基吡啶-2-基)吡啶-2-甲醛
  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
• 作为产物：
  描述：

  6-(乙硫基)-2,2'-联吡啶 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 为溶剂， 生成 6-(乙基亚磺酰)-2,2'-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

文献信息

• An optical resolution of pyridyl and bipyridylethanols and a facile preparation of optically pure oligopyridines
  作者：Jun'ichi Uenishi、Kenji Nishiwaki、Shinichiro Hata、Kaoru Nakamura

  DOI：10.1016/0040-4039(94)80025-1

  日期：1994.10

  A kinetic resolution of racemic pyridyl and bipyridylethanols was performed by Candida antarctica lipase with vinyl acetate in diisopropyl ether, in which (R)-alcohol was acetylated stereoselectively, and both the acetate 2 and the remaining (S)-alcohol 1 were obtained with high enantiomeric excesses. (S0-Oligopyridylethanols, 7 and 8 were prepared by a coupling reaction of (S)-1b and (S)-1e with ethyl

  南极假丝酵母脂肪酶和乙酸乙烯酯在二异丙醚中进行消旋吡啶基和联吡啶乙醇的动力学拆分，其中（R）-醇被立体选择性乙酰化，乙酸酯2和剩余的（S）-醇1均获得了较高的收率。对映体过量。通过（S）-1b和（S）-1e与乙基联吡啶亚砜的偶联反应制备了（S 0-低级吡啶基乙醇，7和8。