2-(p-chloro-o-nitrophenyl)benzo[b]thiophene | 950851-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-chloro-o-nitrophenyl)benzo[b]thiophene
• 英文别名: 2-(4-Chloro-2-nitrophenyl)-1-benzothiophene
• CAS: 950851-88-4
• 化学式: C₁₄H₈ClNO₂S
• 分子量: 289.742
• InChiKey: JDONEMLNQJESDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-chloro-o-nitrophenyl)benzo[b]thiophene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 以94%的产率得到2-(benzo[b]thiophen-2-yl)-5-chloroaniline
  参考文献：
  名称：

  Heck-like coupling and Pictet–Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines

  摘要：

  A series of 6-arylbenzothieno[3,2-c] quinolines were synthesised in three steps from benzo[b] thiophene. After a selective Heck-type coupling of benzo[b] thiophene with different o-nitroaryl bromides to obtain 2-(o-nitroaryl) benzo[b] thiophenes, corresponding 2-(benzo[ b] thiophen-2-yl) anilines were involved in a Pictet-Spengler reaction to form the quinoline cycle. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.110
• 作为产物：
  描述：

  2-溴-5-氯硝基苯 、 苯并噻吩 在 palladium diacetate potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以42%的产率得到2-(p-chloro-o-nitrophenyl)benzo[b]thiophene
  参考文献：
  名称：

  Heck-like coupling and Pictet–Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines

  摘要：

  A series of 6-arylbenzothieno[3,2-c] quinolines were synthesised in three steps from benzo[b] thiophene. After a selective Heck-type coupling of benzo[b] thiophene with different o-nitroaryl bromides to obtain 2-(o-nitroaryl) benzo[b] thiophenes, corresponding 2-(benzo[ b] thiophen-2-yl) anilines were involved in a Pictet-Spengler reaction to form the quinoline cycle. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.110

文献信息

• Heck-like coupling and Pictet–Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines
  作者：Emilie David、Stéphane Pellet-Rostaing、Marc Lemaire

  DOI：10.1016/j.tet.2007.05.110

  日期：2007.9

  A series of 6-arylbenzothieno[3,2-c] quinolines were synthesised in three steps from benzo[b] thiophene. After a selective Heck-type coupling of benzo[b] thiophene with different o-nitroaryl bromides to obtain 2-(o-nitroaryl) benzo[b] thiophenes, corresponding 2-(benzo[ b] thiophen-2-yl) anilines were involved in a Pictet-Spengler reaction to form the quinoline cycle. (C) 2007 Published by Elsevier Ltd.