N-pyrrolidinyl-2-pyridinesulfenamide | 1645264-02-3

• 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-pyrrolidinyl-2-pyridinesulfenamide
• 英文别名: 2-Pyrrolidin-1-ylsulfanylpyridine；2-pyrrolidin-1-ylsulfanylpyridine
• CAS: 1645264-02-3
• 化学式: C₉H₁₂N₂S
• 分子量: 180.274
• InChiKey: XVHQTZNCMRZQTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-pyrrolidinyl-2-pyridinesulfenamide 在 ruthenium(III) trichloride hydrate 、 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 以119 mg的产率得到2-(pyrrolidin-1-ylsulfonyl)pyridine
  参考文献：
  名称：

  Heteroaryl 2‐Sulfonamide Synthesis by S_N2 Reaction–Oxidation Cascade

  摘要：

  Heteroaryl 2‐sulfonamides are an important structural moiety in drug discovery. However, reports of the efficient synthesis of these scaffolds are rare. Herein we disclose new reaction conditions to synthesize heteroaryl 2‐sulfonamides from disulfanes and amines through an S_N2‐oxidation cascade. The approach is compatible with a wide variety of heteroaryl and amine substrates and can be conducted on a gram scale. A potential Werner Syndrome Protein (WRN) small molecule inhibitor H3B‐968 was also synthesized by this method.

  DOI：

  10.1002/ejoc.202400235
• 作为产物：
  描述：

  四氢吡咯 、 2,2'-二硫二吡啶 在 silver nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 N-pyrrolidinyl-2-pyridinesulfenamide
  参考文献：
  名称：

  Heteroaryl 2‐Sulfonamide Synthesis by S_N2 Reaction–Oxidation Cascade

  摘要：

  Heteroaryl 2‐sulfonamides are an important structural moiety in drug discovery. However, reports of the efficient synthesis of these scaffolds are rare. Herein we disclose new reaction conditions to synthesize heteroaryl 2‐sulfonamides from disulfanes and amines through an S_N2‐oxidation cascade. The approach is compatible with a wide variety of heteroaryl and amine substrates and can be conducted on a gram scale. A potential Werner Syndrome Protein (WRN) small molecule inhibitor H3B‐968 was also synthesized by this method.

  DOI：

  10.1002/ejoc.202400235

文献信息

• Hypervalent Iodine(III)-Promoted Metal-Free S-H Activation: An Approach for the Construction of S-S, S-N, and S-C Bonds
  作者：Eakkaphon Rattanangkool、Watanya Krailat、Tirayut Vilaivan、Preecha Phuwapraisirisan、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1002/ejoc.201402180

  日期：2014.8

  thiols with (diacetoxyiodo)benzene (DIB) has been explored in the preparation of symmetrical disulfides and sulfenamides. Disulfides can be produced in excellent yields (75–95 %) upon treatment of thiols with DIB. The reaction was complete in less than five minutes at room temperature. Aliphatic, aromatic, and heteroaromatic thiols are compatible with this transformation. Moreover, heteroaromatic disulfides

  在对称二硫化物和次磺酰胺的制备中，已经探索了用（二乙酰氧基碘）苯 (DIB) 活化硫醇的硫原子。用 DIB 处理硫醇后，二硫化物可以以极好的收率 (75–95%) 产生。在室温下反应在不到五分钟内完成。脂肪族、芳香族和杂芳香族硫醇与这种转化相容。此外，从杂芳族硫醇获得的杂芳族二硫化物在碱存在下进一步与亲核胺反应，以一锅法以相当到良好的产率（43-90%）提供相应的次磺酰胺。该方法成功地扩展到吲哚作为一种代表性的富电子芳香化合物，从而可以在一锅中成功构建 S-C 键。
• Heteroaryl 2‐Sulfonamide Synthesis by S_N2 Reaction–Oxidation Cascade
  作者：Lu Yan、Chaofan Xu

  DOI：10.1002/ejoc.202400235

  日期：——

  Heteroaryl 2‐sulfonamides are an important structural moiety in drug discovery. However, reports of the efficient synthesis of these scaffolds are rare. Herein we disclose new reaction conditions to synthesize heteroaryl 2‐sulfonamides from disulfanes and amines through an S_N2‐oxidation cascade. The approach is compatible with a wide variety of heteroaryl and amine substrates and can be conducted on a gram scale. A potential Werner Syndrome Protein (WRN) small molecule inhibitor H3B‐968 was also synthesized by this method.