2-(4-甲氧基苯基)-1-苯并噻吩-3-甲醛 | 693228-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-(4-甲氧基苯基)-1-苯并噻吩-3-甲醛
• 英文名称: 2-(4-methoxyphenyl)-1-benzothiophene-3-carbaldehyde
• 英文别名: 2-(4'-anisyl)-benzo[b]thiophene-3-carboxaldehyde
• CAS: 693228-22-7
• 化学式: C₁₆H₁₂O₂S
• 分子量: 268.336
• InChiKey: HEDJMSAHZMTMRD-UHFFFAOYSA-N

物化性质

• 熔点：
  81.3-84.9 °C
• 沸点：
  465.5±40.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.5
• 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-甲氧基苯基)-1-苯并噻吩-3-甲醛 在 sodium acetate 、 乙酸酐 作用下， 反应 18.0h， 以44%的产率得到4-(2-(4-methoxyphenyl)-benzo[b]thiophen-3-ylmethylene)-2-phenyl-4H-oxazol-5-one
  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-溴苯甲醚 在 palladium diacetate 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以64%的产率得到2-(4-甲氧基苯基)-1-苯并噻吩-3-甲醛
  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

文献信息

• Scaleable Preparation of Sensitive Functionalized Aromatics and Heteroaromatics via Directed Metalation Using tmpZnCl·LiCl
  作者：Tomke Bresser、Gabriel Monzon、Marc Mosrin、Paul Knochel

  DOI：10.1021/op1001935

  日期：2010.11.19

  A range of functional aryl and heteroaryl zinc reagents were prepared in THF via directed zincation using the previously reported amide base tmpZnCl·LiCl. These metalation reactions were carried out on 50 mmol scale. Diverse sensitive functional groups such as a nitro group, an aldehyde, an ester, and a nitrile are tolerated. Furthermore, the resulting zinc intermediates show excellent reactivity towards

  使用先前报道的酰胺基tmpZnCl·LiCl，通过定向锌化反应在THF中制备了一系列功能性芳基和杂芳基锌试剂。这些金属化反应以50mmol规模进行。容许各种敏感的官能团，例如硝基，醛，酯和腈。此外，所得的锌中间体显示出对各种类型的亲电试剂的优异反应性，例如Pd催化的交叉偶联反应或Cu催化的酰化和烯丙基化。在所有情况下，均已将金属化速率与相应的小规模反应（1-2 mmol）进行了比较。此外，已经证明了从水相中回收有价值的tmp-H。
• 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.
• US6025382A
  申请人：——

  公开号：US6025382A

  公开（公告）日：2000-02-15
• 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.