N-(pyridin-3-yl)thiophene-2-sulfonamide | 53442-50-5

• 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
• 英文名称: N-(pyridin-3-yl)thiophene-2-sulfonamide
• 英文别名: thiophene-2-sulfonic acid pyridin-3-ylamide；N-pyridin-3-ylthiophene-2-sulfonamide
• CAS: 53442-50-5
• 化学式: C₉H₈N₂O₂S₂
• mdl: MFCD02071682
• 分子量: 240.307
• InChiKey: DJOJRYLDSBEZMU-UHFFFAOYSA-N

物化性质

• 沸点：
  421.3±43.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-硝基吡啶 、 sodium thiophene-2-sulfinate 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 sodium hydrogen sulfate 、 iron(II) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以81%的产率得到N-(pyridin-3-yl)thiophene-2-sulfonamide
  参考文献：
  名称：

  Iron-Catalyzed N-Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources

  摘要：

  One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.

  DOI：

  10.1021/acs.joc.5b00130

文献信息

• Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters
  作者：Jianmin Zhang、Hanna I. Pettersson、Carly Huitema、Chunying Niu、Jiang Yin、Michael N. G. James、Lindsay D. Eltis、John C. Vederas

  DOI：10.1021/jm061425k

  日期：2007.4.1

  The 3C-like protease (3CL(pro)), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CL(pro) inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.
• Iron-Catalyzed <i>N</i>-Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources
  作者：Weixi Zhang、Junyao Xie、Bin Rao、Meiming Luo

  DOI：10.1021/acs.joc.5b00130

  日期：2015.4.3

  One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.