1-phenyl-2-(2-pyridylsulfanyl)ethanol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenyl-2-(2-pyridylsulfanyl)ethanol
• 英文别名: 1-phenyl-2-(pyridin-2-ylthio)ethan-1-ol；1-Phenyl-2-pyridin-2-ylsulfanylethanol
• 化学式: C₁₃H₁₃NOS
• mdl: MFCD12761790
• 分子量: 231.318
• InChiKey: RXHFVORLJULYTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-巯基吡啶 在 四丁基氟化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.0h， 生成 1-phenyl-2-(2-pyridylsulfanyl)ethanol
  参考文献：
  名称：

  Reaction of 2-Trimethylsilylmethylthiopyridine Promoted by a Fluoride Ion: The First Example of Generation of 2-Pyridylthiomethylcarbanion

  摘要：

  2-Trimethylsilylmethylthiopyridine prepared readily by the reaction of 2-mercaptopyridine with chloromethyltrimethylsilane in the presence of potassium carbonate reacts with carbonyl compounds in the presence of a catalytic amount of tetrabutylammonium fluoride (TBAF) to give 2-(2-pyridylthio)ethanols. This reaction is the first example of generation and introduction of 2-pyfidylthiomethyl-carbanion.

  DOI：

  10.3987/com-93-6383

文献信息

• Simple approach to modular chiral scaffolds: binding functional sulfur nucleophiles to Cinchona alkaloids
  作者：Mariola Zielińska-Błajet、Przemysław J. Boratyński、Łukasz Sidorowicz、Jacek Skarżewski

  DOI：10.1016/j.tet.2015.05.035

  日期：2016.5

  stereoselectively attached to the Cinchona alkaloid scaffolds. The SN2 reactions of thiolates with alkaloid mesylate and epoxide introduced metal-complexing moieties, including the heterocyclic systems of pyridine and 1,10-phenanthroline. The respective H-bond donating thiourea and salane motifs were formed in an additional step. The modified Cinchona alkaloids were tested in the metal-catalyzed Henry and

  在金鸡纳生物碱支架上选择性和立体选择性地连接了一系列功能模块。硫醇盐与生物碱甲磺酸盐和环氧化物的S N 2反应引入了金属络合部分，包括吡啶和1,10-菲咯啉的杂环系统。在另外的步骤中形成了各自的氢键供体的硫脲和萨拉烷基序。在金属催化的亨利和Tsuji-Trost反应中测试了改性的金鸡纳生物碱。
• Visible-Light-Induced Organophotocatalytic Difunctionallization: Open-Air Hydroxysulfurization of Aryl Alkenes with Aryl Thiols
  作者：Jee Eun Hong、Yeonghun Jung、Dahye Min、Minji Jang、Soomin Kim、Jiyong Park、Yohan Park

  DOI：10.1021/acs.joc.2c00595

  日期：2022.6.3

  situ generated hydroperoxyl radicals from O2 in air react with benzylic radicals, which restrains the reaction between benzylic radicals and the acidic form of thiols in a classical thiol–ene radical reaction. We show that difunctionalization is possible due to the choice of bases, diluted substrate concentrations, increment in catalyst loading, and selection of suitable aryl thiols under aerobic conditions

  在此，我们报道了一种区域选择性可见光诱导的有机光氧化还原催化双官能化方法，以芳基烯烃和芳基硫醇为底物制备 β-羟基硫化物。该反应提供了广泛的芳基烯烃（从简单的苯乙烯到复杂的生物活性化合物）和芳基硫醇（从各种杂芳族硫醇到非杂芳族硫醇）的底物范围（总共 45 个实例，产率高达 88%）。基于结合的实验和计算研究，我们证明了从 O 2原位产生的氢过氧自由基在空气中与苄基自由基反应，从而抑制了经典硫醇-烯自由基反应中苄基自由基与硫醇的酸性形式之间的反应。我们表明，由于碱的选择、稀释的底物浓度、催化剂负载量的增加以及在有氧条件下选择合适的芳基硫醇，双功能化是可能的。考虑到杂芳族硫醇的生物学重要性以及缺乏安装它们的方法，我们的方法提供了一个衍生各种含有芳族元素的 β-羟基硫化物的平台。
• Reaction of 2-Trimethylsilylmethylthiopyridine Promoted by a Fluoride Ion: The First Example of Generation of 2-Pyridylthiomethylcarbanion
  作者：Shinya Kohra、Hiroshi Ueda、Yoshinori Tominaga

  DOI：10.3987/com-93-6383

  日期：——

  2-Trimethylsilylmethylthiopyridine prepared readily by the reaction of 2-mercaptopyridine with chloromethyltrimethylsilane in the presence of potassium carbonate reacts with carbonyl compounds in the presence of a catalytic amount of tetrabutylammonium fluoride (TBAF) to give 2-(2-pyridylthio)ethanols. This reaction is the first example of generation and introduction of 2-pyfidylthiomethyl-carbanion.