3-氰基-4-硝基吡啶 | 1003711-76-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 3-氰基-4-硝基吡啶
• 英文名称: 4-Nitropyridine-3-carbonitrile
• CAS: 1003711-76-9
• 化学式: C₆H₃N₃O₂
• mdl: MFCD09835270
• 分子量: 149.109
• InChiKey: RSWUDFDGDSLOGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氰基-4-硝基吡啶 、 4-甲苯硫酚 在 potassium phosphate 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到4-(p-tolylthio)nicotinonitrile
  参考文献：
  名称：

  C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

  摘要：

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.07.012

文献信息

• Process for producing aminonitropyridines
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0735025B1

  公开（公告）日：1998-07-01
• US5648496A
  申请人：——

  公开号：US5648496A

  公开（公告）日：1997-07-15