2-(methylthio)-3-(phenylethynyl)pyridine | 1448146-91-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(methylthio)-3-(phenylethynyl)pyridine
• 英文别名: 2-Methylsulfanyl-3-(2-phenylethynyl)pyridine
• CAS: 1448146-91-5
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: DCQFHTOBLLQJRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：

  2-(methylthio)-3-(phenylethynyl)pyridine 在 碘 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以73%的产率得到3-iodo-2-phenylthieno[2,3-b]pyridine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1055/s-0033-1338442
• 作为产物：
  描述：

  3-溴-2-氯吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(methylthio)-3-(phenylethynyl)pyridine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1055/s-0033-1338442

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。