2-(2'-benzonitrile)-3-(2,2,2-trifluoroethoxy)benzo[b]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(2'-benzonitrile)-3-(2,2,2-trifluoroethoxy)benzo[b]thiophene
• 英文别名: 2-[3-(2,2,2-Trifluoroethoxy)-1-benzothiophen-2-yl]benzonitrile
• 化学式: C₁₇H₁₀F₃NOS
• 分子量: 333.334
• InChiKey: RCFOJHPWMBFTHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴苯并噻吩 在 二环己烷并-18-冠醚-6 、 copper(l) iodide 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.75h， 生成 2-(2'-benzonitrile)-3-(2,2,2-trifluoroethoxy)benzo[b]thiophene
  参考文献：
  名称：

  An efficient phosphine-free palladium coupling for the synthesis of new 2-arylbenzo[b]thiophenes

  摘要：

  Straightforward and rapid access to 2-arylbenzo[b]thiophenes has been developed. It involved a catalytic coupling of 3-activated benzo[b]thiophenes with several aryl halides in the presence of a phosphine-free palladium system. In case of fragile functional groups such as aldehydes, a quaternary ammonium was used as an additive as with the other substrates, the coupling performed better and faster in the presence of a crown ether, the best one being DCH-18-C-6, with good yields and low reaction times. This method would provide a direct access to novel structures of biological interest. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.011

文献信息

• Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus
  作者：Jérémie Fournier dit Chabert、Béatrice Marquez、Luc Neville、Lionel Joucla、Sylvie Broussous、Pascale Bouhours、Emilie David、Stéphane Pellet-Rostaing、Bernard Marquet、Nicole Moreau、Marc Lemaire

  DOI：10.1016/j.bmc.2007.04.023

  日期：2007.7

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.