3-nitro-2-(thiophen-3-yl)pyridine | 1319733-94-2

• 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
• 英文名称: 3-nitro-2-(thiophen-3-yl)pyridine
• 英文别名: 3-nitro-2-thiophen-3-ylpyridine
• CAS: 1319733-94-2
• 化学式: C₉H₆N₂O₂S
• 分子量: 206.225
• InChiKey: QEFFCPANLDTVDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.03
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-nitro-2-(thiophen-3-yl)pyridine 在 1,2-双(二苯基膦)乙烷 作用下， 反应 5.0h， 以60%的产率得到8H-thieno[3',2':4,5]pyrrolo[3,2-b]pyridine
  参考文献：
  名称：

  Solvent-free synthesis of δ-carbolines/carbazoles from 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives using DPPE as a reducing agent

  摘要：

  A green and efficient preparation of functionalized delta-carbolines/carbazoles via reductive ring closure by 1,2-bis(dipenylphosphino)ethane under solvent-free conditions is described. The starting materials 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives are readily prepared through Suzuki-Miyaura cross-coupling reaction from commercially available compounds. And the polar by-product ethane-1,2-diylbis(diphenylphosphine oxide) is easily removed from the relatively polar reaction mixture. Various substituted delta-carbolines/carbazoles are obtained in acceptable yields. It is particularly worth mentioning that substrates with electron-withdrawing groups (EWG) also give the desired products in good yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.027
• 作为产物：
  描述：

  3-噻吩硼酸 、 2-氯-3-硝基吡啶 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以60%的产率得到3-nitro-2-(thiophen-3-yl)pyridine
  参考文献：
  名称：

  Solvent-free synthesis of δ-carbolines/carbazoles from 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives using DPPE as a reducing agent

  摘要：

  A green and efficient preparation of functionalized delta-carbolines/carbazoles via reductive ring closure by 1,2-bis(dipenylphosphino)ethane under solvent-free conditions is described. The starting materials 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives are readily prepared through Suzuki-Miyaura cross-coupling reaction from commercially available compounds. And the polar by-product ethane-1,2-diylbis(diphenylphosphine oxide) is easily removed from the relatively polar reaction mixture. Various substituted delta-carbolines/carbazoles are obtained in acceptable yields. It is particularly worth mentioning that substrates with electron-withdrawing groups (EWG) also give the desired products in good yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.027