2-(4'-chlorophenyl)-benzo[b]thiophene-3-carbonitrile

• 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-(4'-chlorophenyl)-benzo[b]thiophene-3-carbonitrile
• 英文别名: 2-(4-Chlorophenyl)-1-benzothiophene-3-carbonitrile
• 化学式: C₁₅H₈ClNS
• 分子量: 269.754
• InChiKey: VFTOJXZADHFOFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 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：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴苯并噻吩 在 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.5h， 生成 2-(4'-chlorophenyl)-benzo[b]thiophene-3-carbonitrile
  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

• One-pot synthesis of 2,3-substituted benzo[b]thiophenes via Cu(<scp>i</scp>) catalysed intramolecular cyclisation from dithioesters
  作者：Nagarakere. C. Sandhya、Kebbahalli. N. Nandeesh、Kanchugarakoppal. S. Rangappa、Sannaiah. Ananda

  DOI：10.1039/c5ra02114f

  日期：——

  Efficient synthesis of benzo[b]thiophenes from o-halophenyl acetonitrile has been achieved. This novel one-pot procedure involves CuI and pivalic acid catalyzed C–S bond formation using dithioesters followed by a heterocyclization reaction. This efficient protocol has the advantages of one-pot synthesis, short reaction time, good yields (62–78%) and operational simplicity.

  已从邻卤代苯基乙腈高效合成苯并[ b ]噻吩。这种新颖的一锅法涉及使用二硫代酯和CuI和新戊酸催化的C–S键形成，然后进行杂环化反应。这种高效的方法具有一锅法合成，反应时间短，产率高（62-78％）和操作简便的优点。
• 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.
• [EN] COMPOSITION CONTAINING A THIOPHENIC OR BENZOTHIOPHENIC COMPOUND AND EXHIBITING A PUMP NORA INHIBITING ACTIVITY<br/>[FR] COMPOSITIONS CONTENANT UN COMPOSE THIOPHENIQUE OU BENZOTHIOPHENIQUE, PRESENTANT UNE ACTIVITE INHIBITRICE DE POMPE NORA
  申请人：UNIV CLAUDE BERNARD LYON

  公开号：WO2006018544A1

  公开（公告）日：2006-02-23

  La présente invention concerne l'utilisation d'inhibiteurs de pompe efflux NorA de formule (I) : tels que définis à la revendication 1, pour la préparation d'un médicament destiné à potentialiser l'effet d'un agent antimicrobien, ainsi que des compositions pour potentialiser l'effet d'un agent antimicrobien contenant, en tant qu'agent potentialisateur, un tel inhibiteur de pompe efflux NorA.
• An efficient phosphine-free palladium coupling for the synthesis of new 2-arylbenzo[b]thiophenes
  作者：Jérémie Fournier Dit Chabert、Lionel Joucla、Emilie David、Marc Lemaire

  DOI：10.1016/j.tet.2004.02.011

  日期：2004.3

  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.