3-chloro-2-(phenylthio)pyridine | 1174014-08-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloro-2-(phenylthio)pyridine
• 英文别名: 3-chloro-2-phenylsulfanylpyridine
• CAS: 1174014-08-4
• 化学式: C₁₁H₈ClNS
• mdl: MFCD27965539
• 分子量: 221.71
• InChiKey: IYKRPJZSBLTOCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-2-(phenylthio)pyridine 在 sodium hypochlorite 、 溶剂黄146 作用下， 反应 2.0h， 生成 3-chloro-2-benzenesulfonyl-pyridine
  参考文献：
  名称：

  Green Chemical Synthesis of 2-Benzenesulfonyl-pyridine and Related Derivatives

  摘要：

  A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and >99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.

  DOI：

  10.1021/op700060e
• 作为产物：
  描述：

  2,3-二氯吡啶 、 苯硫酚 在 potassium phosphate 、 copper(l) iodide 、 L-脯氨酸 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以84%的产率得到3-chloro-2-(phenylthio)pyridine
  参考文献：
  名称：

  在水两相系统中，铜（I）催化硫醇与芳基卤化物的高效 C-S 交叉偶联

  摘要：

  CuI/L-脯氨酸在水性两相体系中实现了温和方便的 C-S 键形成反应，为合成芳基硫化物的高产率提供了一种简单的方法。

  DOI：

  10.1080/17415993.2010.547197

文献信息

• Efficient synthesis of unsymmetrical heteroaryl thioethers and chalcogenides by alkali hydroxide-mediated S_NAr reactions of heteroaryl halides and dichalcogenides
  作者：Xiantao Ma、Quan Liu、Xiaojuan Jia、Chenliang Su、Qing Xu

  DOI：10.1039/c6ra10517c

  日期：——

  An efficient alkali hydroxide-mediated SNAr reaction of heteroaryl halides has been developed for the practical synthesis of the useful unsymmetrical heteroaryl thioethers and chalcogenides. The usually odorless, easily available, lowly toxic, and easily stored and handled diorganyl dichalcogenides can be used as safer and convenient chalcogen nucleophile precursors and diverse unsymmetrical heteroaryl

  一种有效的碱金属氢氧化物-介导的小号Ñ杂芳基卤化物的反应的Ar已经开发了用于非对称有用的杂芳基硫醚和硫属化物的实际合成。通常无味，易得，低毒，易于保存和处理的二有机基二硫代半乳糖苷可以用作安全，方便的硫属元素亲核体前体，并可以通过该方法以高到高收率获得各种不对称的杂芳基硫属元素化物。
• Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols
  作者：B. Sreedhar、P. Reddy、M. Reddy

  DOI：10.1055/s-0029-1216644

  日期：2009.5

  A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products.

  在水相中，已开发出一种简单高效的合成联芳基硫醚的路线，无需碱和催化剂。各种杂芳基卤化物和硫醇通过SNAr反应，以良好至优异的产率提供了二芳基硫醚。该反应的显著关键特征包括使用水作为廉价且环境友好的反应介质，无需任何额外试剂或催化剂，以及产品易于分离。
• Metal-Free <i>ortho</i>-Selective C–H Borylation of 2-Phenylthiopyridines Using BBr₃
  作者：Gaorong Wu、Binghan Pang、Yangyang Wang、Li Yan、Lu Chen、Tao Ma、Yafei Ji

  DOI：10.1021/acs.joc.1c00520

  日期：2021.4.16

  2-phenylthiopyridines using BBr3 as the boron source under metal-free conditions has been reported. The reaction exhibited site exclusivity, and the synthesized aryl boronates were freely converted to various useful intermediates. Thus, this facile method would be beneficial to synthesize structurally diversified phenylthioethers derivatives and other materials containing boron-nitrogen coordination.

  已经报道了一种在无金属条件下使用BBr 3作为硼源对2-苯基硫代吡啶进行邻位C-H硼化的新途径。该反应表现出位点排他性，并且合成的硼酸芳基酯被自由地转化成各种有用的中间体。因此，这种简便的方法将有利于合成结构上多样化的苯硫醚衍生物和其他含有硼-氮配位的材料。
• Sulfur–silicon bond activation catalysed by Cl/Br ions: waste-free synthesis of unsymmetrical thioethers by replacing fluoride catalysis and fluorinated substrates in SNAr reactions
  作者：Xiaojuan Jia、Lei Yu、Jianping Liu、Qing Xu、Marcel Sickert、Lianhui Chen、Mark Lautens

  DOI：10.1039/c4gc00535j

  日期：——

  In contrast to conventional activation of Nu–SiR3 reagents by F ion attributed to the strong affinity of Si to F, S–Si activation can now be achieved using Cl/Br ions of TBAX as catalysts via formation of weaker X–Si bonds and Me3Si–X. This led to a waste-free synthesis of unsymmetrical thioethers via F-free SNAr reactions of activated (hetero)aryl halides and RS–SiMe3, with recovery of the useful Me3Si–X reagent in high yields.

  与传统通过氟离子激活Nu–SiR3试剂（归因于硅对氟的强亲和力）相比，S–Si激活现在可以通过TBAX的氯/溴离子作为催化剂实现，这通过形成较弱的X–Si键和Me3Si–X。这样可以实现无废物合成不对称的硫醚，通过活化的（杂）芳基卤化物和RS–SiMe3进行无氟的SNAr反应，并高产率回收有用的Me3Si–X试剂。