2-(3-pyridyl)-3-cyanothiophene | 944550-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(3-pyridyl)-3-cyanothiophene
• 英文别名: 3-(3-cyanothiophen-2-yl)pyridine；2-Pyridin-3-ylthiophene-3-carbonitrile
• CAS: 944550-53-2
• 化学式: C₁₀H₆N₂S
• 分子量: 186.237
• InChiKey: XYHBAUWDSLDMGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-pyridyl)-3-cyanothiophene 、 间溴三氟甲苯 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 18.0h， 以42%的产率得到2-(3-pyridyl)-5-(α,α,α-trifluoro-m-tolyl)-3-cyanothiophene
  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-溴吡啶 、 3-氰基噻吩 在 palladium diacetate 二环己烷并-18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以33%的产率得到2-(3-pyridyl)-3-cyanothiophene
  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

• Palladium-Catalysed C2 or C5 Direct Arylation of 3-Substituted Thiophenes with Aryl Bromides
  作者：Henri Doucet、Jia Dong、David Roy、Reny Roy、Marina Ionita

  DOI：10.1055/s-0030-1260213

  日期：2011.11

  catalyst for the direct arylation of 3-substituted thiophene derivatives. The regioselectivity of the arylation strongly depends on the thiophene substituent and also on the nature of the aryl bromide. When using 3-formyl, 3-cyano, 3-methyl, 3-hydroxymethyl or 3-bromothiophene, the 2-arylated thiophenes were obtained with 76-95% regioselectivity; whereas, the arylation of 3-formylthiophene diethylacetal

  钯（OAc）2发现/ dppb体系是3-取代的噻吩衍生物直接芳基化的有效催化剂。芳基化的区域选择性在很大程度上取决于噻吩取代基以及芳基溴化物的性质。当使用3-甲酰基，3-氰基，3-甲基，3-羟甲基或3-溴噻吩时，以76-95％的区域选择性得到2-芳基化的噻吩。而3-甲酰基噻吩二乙基缩醛或3-乙酰基噻吩的芳基化得到5-芳基噻吩的区域选择性为52-90％。拥挤的芳基溴化物的使用有利于C5处的芳基化。这些反应仅使用0.1mol％的催化剂进行。此外，已经发现该方法耐受芳基溴化物上的各种官能团，例如甲酰基，丙酰基，苯甲酰基，腈和硝基。 催化-钯-噻吩-芳基化-CH键活化
• 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.