3-(methylthio)-2-(phenylethynyl)pyridine | 900535-85-5

• 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-(methylthio)-2-(phenylethynyl)pyridine
• 英文别名: 2-(2-phenylethynyl)-3-methylthiopyridine；3-(Methylthio)-2-(phenylethynyl)pyridine；3-methylsulfanyl-2-(2-phenylethynyl)pyridine
• CAS: 900535-85-5
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: JYMIDYVUMBOJFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-(methylthio)-2-(phenylethynyl)pyridine 在 oxone 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以81%的产率得到3-iodo-2-phenylthieno[3,2-b]pyridine
  参考文献：
  名称：

  Oxone®-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153614
• 作为产物：
  描述：

  3-(甲基硫代)吡啶 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 N,N-二甲基乙醇胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 3-(methylthio)-2-(phenylethynyl)pyridine
  参考文献：
  名称：

  New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine

  摘要：

  The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by BuLi-LiDMAE superbase followed by Sonogashira coupling and halogenocyclization producing the fused heterocycles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.008

文献信息

• Cascade Radical Annulation of 2-Alkynylthio(seleno)anisoles with Acetone or Acetonitrile: Synthesis of 3-Acetomethyl- or Cyanomethyl-Substituted Benzothio(seleno)phenes
  作者：Tao Cai、Fangqi Shen、Yuqi Ni、Huiting Xu、Runpu Shen、Yuzhen Gao

  DOI：10.1021/acs.joc.0c02444

  日期：2021.1.1

  for the direct preparation of 3-aceto(cyano)methyl-substituted benzothio(seleno)phenes has been achieved through C(sp3)–H bond activation of easily available acetone or acetonitrile and cascade radical cyclization reaction. In this cascade radical cyclization reaction, C(sp2)–C(sp3) and C(sp2)–S bonds, as well as benzenethio(seleno)phene skeletons, can be built along with the cleavage of the C(sp3)–S

  通过容易获得的丙酮或乙腈的C（sp 3）-H键活化和级联自由基环化反应，已经实现了直接制备3-乙酰基（氰基）甲基取代的苯并硫基（硒代）苯的有效方法。在此级联自由基环化反应中，可以随C（sp）的裂解构建C（sp 2）–C（sp 3）和C（sp 2）–S键以及苯硫基（硒代）苯骨架。3）– S键，证明这种方法具有较高的步骤经济性和效率。
• Regiocontrolled SNAr Reaction on 2,3-Dihalopyridines with NaSMe To Obtain Bromo(methylthio)pyridines as Key Precursors of 3-Halo-2-(hetero)arylthieno[2,3-b]pyridines and Thieno[3,2-b]pyridines
  作者：Maria-João Queiroz、Agathe Begouin、Daniela Peixoto

  DOI：10.1055/s-0033-1338442

  日期：——

  The synthesis of 3-halo-2-(hetero) arylthieno[2,3-b]pyridines and 3-halo-2-(hetero) arylthieno[3,2-b]pyridines has been performed through a three-step methodology from 3-bromo-2-chloropyridine or 2-bromo-3-fluoropyridine, respectively. The key step of this methodology is the formation of the required bromo(methylthio)pyridines by a regiocontrolled nucleophilic aromatic substitution (SNAr) with sodium methanethiolate (NaSMe). Then, the Sonogashira coupling with (hetero)arylalkynes followed by a halocyclization with bromine or iodine, afforded the expected 3-halo-2-(hetero)arylthienopyridines.
• New efficient access to thieno[3,2-b]pyridine derivatives via regioselective lithiation of 3-methylthiopyridine
  作者：Corinne Comoy、Estelle Banaszak、Yves Fort

  DOI：10.1016/j.tet.2006.04.008

  日期：2006.6

  The synthesis of thieno[3,2-b]pyridines was achieved using a three-step process allowing the construction of the thiophenic ring with 17-34% overall yields. The key step was the regioselective lithiation-bromination of the 3-methylthiopyridine induced by BuLi-LiDMAE superbase followed by Sonogashira coupling and halogenocyclization producing the fused heterocycles. (c) 2006 Elsevier Ltd. All rights reserved.
• Oxone®-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes
  作者：Xinyu Chen、Zhebing Zhang、Tao Sun、Haokun Cai、Yuzhen Gao、Tao Cai、Tianbo Shang、Yanjuan Luo、Guoqi Yu、Hualiang Shen、Guofeng Wu、Yanlin Hei、Enmin Li、Gang Fan

  DOI：10.1016/j.tetlet.2021.153614

  日期：2022.2