2-(4'-benzonitrile)-benzo[b]thiophene-3-carboxaldehyde

• 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'-benzonitrile)-benzo[b]thiophene-3-carboxaldehyde
• 英文别名: 4-(3-formylbenzo[b]thiophen-2-yl)-benzonitrile；4-(3-formylbenzo[b]thiophen-2-yl)benzonitrile；4-(3-Formyl-1-benzothiophen-2-yl)benzonitrile
• 化学式: C₁₆H₉NOS
• 分子量: 263.32
• InChiKey: FURVINZRJNFMOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  马尿酸 、 2-(4'-benzonitrile)-benzo[b]thiophene-3-carboxaldehyde 在 sodium acetate 、 乙酸酐 作用下， 反应 18.0h， 以48%的产率得到
  参考文献：
  名称：

  Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.04.023
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 4-溴苯腈 在 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以65%的产率得到2-(4'-benzonitrile)-benzo[b]thiophene-3-carboxaldehyde
  参考文献：
  名称：

  无磷钯催化苯并噻吩与芳基溴化物的直接C2-芳基化

  摘要：

  发现无配体的Pd（OAc）2在低催化剂浓度下非常有效地催化苯并噻吩衍生物的直接C2-芳基化。该反应可使用少至0.5-0.1 mol％的催化剂，具有缺电子和一些富电子的芳基溴化物来进行。苯并噻吩的C3处甲基或甲酰基取代基的存在对反应性的影响很小，甚至C3处的溴取代基也是可以容忍的。已经使用了芳基溴上的各种官能团，例如腈，硝基，乙酰基，甲酰基，酯，氯，氟或三氟甲基。

  DOI：

  10.1016/j.tet.2013.06.037

文献信息

• Preparation of Aryl and Heteroaryl Indium(III) Reagents by the Direct Insertion of Indium in the Presence of LiCl
  作者：Yi-Hung Chen、Paul Knochel

  DOI：10.1002/anie.200802292

  日期：2008.9.22
• 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.