2-(thiophen-3-yl)quinolin-4(1H)-one | 110802-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(thiophen-3-yl)quinolin-4(1H)-one
• 英文别名: 2-(3-Thienyl)-4-quinolinol；2-thiophen-3-yl-1H-quinolin-4-one
• CAS: 110802-17-0
• 化学式: C₁₃H₉NOS
• 分子量: 227.287
• InChiKey: APZNAUYADDSJTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 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：
  57.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(thiophen-3-yl)quinolin-4(1H)-one 在 potassium iodide 作用下， 以 甲醇 为溶剂， 以61 %的产率得到3-iodo-2-(thiophen-3-yl)quinolin-4(1H)-one
  参考文献：
  名称：

  功能化喹诺酮的选择性电化学卤化

  摘要：

  这项工作描述了在电化学条件下喹啉-4(1 H )-酮的有效 C3-H 卤化，其中卤化钾既充当卤化剂又充当电解质。该方案提供了在不分开的电池中方便地获得不同的卤代喹啉-4(1 H )-酮的方法，这些卤代喹啉-4(1 H)-酮具有独特的区域选择性、广泛的底物范围以及采用方便、环保的电解进行的克级合成。机理研究表明，卤素自由基可以促进喹诺酮类药物中N-H键的活化。

  DOI：

  10.1021/acs.joc.3c00876
• 作为产物：
  描述：

  2'-溴苯乙酮 在 5A molecular sieve sodium hydroxide 、 copper(l) iodide 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 26.0h， 生成 2-(thiophen-3-yl)quinolin-4(1H)-one
  参考文献：
  名称：

  顺序铜催化的酰胺化碱介导的营地环化：由邻卤代苯酮分两步合成2-芳基-4-喹诺酮类化合物

  摘要：

  对于2-芳基-和2-乙烯基-4-喹诺酮的制备直接两步法，其利用的铜催化的酰胺化ö -halophenones然后将所得的碱促进环化营ñ - （2 -ketoaryl描述了酰胺。使用CuI（一种二胺配体）和碱作为催化剂体系，对于一系列芳基，杂芳基和乙烯基酰胺，酰胺化反应的收率很高。随后的营地环化有效地提供了所描述条件的所需4-喹诺酮类药物。

  DOI：

  10.1021/jo701384n

文献信息

• An Efficient Synthesis of ( <scp>1‐Methyl</scp> )‐2‐phenyl‐4‐quinolones from ( <scp> <i>N</i> ‐Methyl </scp> )isatoic Anhydride
  作者：Jae In Lee

  DOI：10.1002/bkcs.12239

  日期：2021.4

  substitution of (N‐methyl)isatoic anhydride with N,O‐dimethylhydroxylamine hydrochloride in CH3CN gave N‐methoxy‐N‐methyl 2‐(N‐methyl)aminobenzamide, which was treated with ethynyllithium reagents to afford 1‐[2‐(N‐methyl)amino]‐3‐phenyl‐2‐propyn‐1‐ones. The 6‐endo cyclization of 1‐[2‐(N‐methyl)amino]‐3‐phenyl‐2‐propyn‐1‐ones using NaOCH3 in CH3OH at 65 °C gave various (1‐methyl)‐2‐phenyl‐4‐quinolone

  用CH 3 CN中的N，O-二甲基羟胺盐酸盐将（N-甲基）乙酸酐进行酰基取代，得到N-甲氧基-N-甲基2-（N-甲基）氨基苯甲酰胺，用乙炔基锂试剂处理后得到1- [ 2-（（N-甲基）氨基] -3-苯基-2-丙炔-1-酮。6-内的1- [2-（环化ñ -甲基）氨基] -3-苯基-2-丙炔-1-酮使用的NaOCH 3在CH 3在65℃下，得到OH各种（1-甲基）-2- -苯基-4-喹诺酮衍生物，收率高。
• Regioselective Perfluoroalkylation of 4‐Quinolones Using Sodium Perfluoroalkyl Sulfinates
  作者：Li Dong、Xiaoqing Wang、Yudi Nie、Shuo Yu、Haotong Li、Qian Zhao、Zixuan Fan、Yuqian Wang、Xiaoting Tan、Zhengsen Yu

  DOI：10.1002/ejoc.202200842

  日期：2022.10.7

  series of C-3 position perfluoroalkylated 4-quinolones were obtained smoothly via radical pathway in the presence of RfSO2Na and (NH4)2S2O8. The protocol features broad substrates scope, high regioselectivity, transition metal-free, and easily available fluorinating reagents, exhibiting potential application value for obtaining bioactive compounds.

  在R f SO 2 Na 和(NH 4 ) 2 S 2 O 8存在下，通过自由基途径顺利获得了一系列C-3位全氟烷基化4-喹诺酮类化合物。该方案具有底物范围广、区域选择性高、不含过渡金属、易于获得的氟化试剂等特点，在获得生物活性化合物方面具有潜在的应用价值。
• Synthesis of 4-Quinolones via a Carbonylative Sonogashira Cross-Coupling Using Molybdenum Hexacarbonyl as a CO Source
  作者：Linda Åkerbladh、Patrik Nordeman、Matyas Wejdemar、Luke R. Odell、Mats Larhed

  DOI：10.1021/jo502400h

  日期：2015.2.6

  A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products after only 20 min of microwave (MW) heating at 120 degrees C. The second method (B) is a gas-free one-pot two-step sequence which runs at room temperature, allowing the use of sensitive substituents (e.g., nitro and bromide groups). For both protocols, molybdenum hexacarbonyl was used as a solid source of CO.
• C-2 phenyl replacements to obtain potent quinoline-based <i>Staphylococcus aureus</i> NorA inhibitors
  作者：Tommaso Felicetti、Gianmarco Mangiaterra、Rolando Cannalire、Nicholas Cedraro、Donatella Pietrella、Andrea Astolfi、Serena Massari、Oriana Tabarrini、Giuseppe Manfroni、Maria Letizia Barreca、Violetta Cecchetti、Francesca Biavasco、Stefano Sabatini

  DOI：10.1080/14756366.2020.1719083

  日期：2020.1.1

  NorA is the most studied efflux pump of Staphylococcus aureus and is responsible for high level resistance towards fluoroquinolone drugs. Although along the years many NorA efflux pump inhibitors (EPIs) have been reported, poor information is available about structure-activity relationship (SAR) around their nuclei and reliability of data supported by robust assays proving NorA inhibition. In this regard, we focussed efforts on the 2-phenylquinoline as a promising chemotype to develop potent NorA EPIs. Herein, we report SAR studies about the introduction of different aryl moieties on the quinoline C-2 position. The new derivative 37a showed an improved EPI activity (16-fold) with respect to the starting hit 1. Moreover, compound 37a exhibited a high potential in time-kill curves when combined with ciprofloxacin against SA-1199B (norA+). Also, 37a exhibited poor non-specific effect on bacterial membrane polarisation and showed an improvement in terms of "selectivity index" in comparison to 1.
• US4728647A
  申请人：——

  公开号：US4728647A

  公开（公告）日：1988-03-01