2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one

• 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-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 2-(2-fluorophenyl)-2,3-dihydro-1H-quinolin-4-one
• 化学式: C₁₅H₁₂FNO
• 分子量: 241.265
• InChiKey: DWKLFSRCLCXSRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴代十二烷 、 2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以24%的产率得到4-Dodecoxy-2-(2-fluorophenyl)quinoline
  参考文献：
  名称：

  Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents

  摘要：

  合成了3个系列共33种喹诺酮化合物:2-(2-、3-和4-氟苯基)-4-O-烷基(C$_{5-15}$)喹诺啉(7a-k、8a-k和9a-k),由2-(2-、3-和4-氟苯基)-2,3-二氢喹啉-4(1H)-酮(4、5和6)在DMF中用卤代烷在碱性条件下反应制得。新化合物7a-k、8a-k和9a-k由黄酮酮4-6制备,可视为一步反应合成喹诺啉的新前体。所有目标化合物(7a-k、8a-k和9a-k)均对其体外抗菌活性进行了评价,在九种试验微生物中它们对耻垢分枝杆菌的活性最强,最高抑制浓度(MIC)为62.5-500 $\mu g/ mL,表明它们有可能用作抗结核剂。其中8a-k(间氟苯基)对耻垢分枝杆菌的活性最强(MIC, 62.5-125 $\mu g/ mL)。新合成的标题化合物也用DPPH•自由基清除法和FRAP法对其体外抗氧化活性进行了评价。它们在低浓度(mg/mL)下的SC$_{50}$值范围分别为0.03-12.48 mg/mL(DPPH•)和0-722 $\mu M$(FRAP)。化合物7a-k、8a-k和9a-k的抗氧化结果表明,烷基链的长度与抗氧化能力负相关。

  DOI：

  10.3906/kim-1501-112
• 作为产物：
  描述：

  1-(2-aminophenyl)-3-(2-fluorophenyl)prop-2-en-1-one 在 silica chloride 作用下， 反应 0.1h， 以88%的产率得到2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  在无溶剂条件下使用二氧化硅作为新型催化剂简单高效地合成 2-Aryl-2,3-Dihydroquinolin-4(1H)-ones

  摘要：

  描述了一种在无溶剂条件下使用氯化硅 (SiO2Cl) 从相应的 2-氨基查耳酮合成 2-芳基-2,3-二氢喹啉-4(1H)-酮的温和、高效和高产的方法. 合成了一系列包含给电子和吸电子取代基的 2-aryl-2,3-dihydroquinolin-4(1H)-ones。

  DOI：

  10.1080/00397910903097252

文献信息

• A general and efficient synthesis of 5,6-dihydrodibenzo[b,h][1,6]naphthyridine derivatives
  作者：Jeremy C. Dobrowolski、Alice Katen、Benjamin H. Fraser、Mohan Bhadbhade、David StC. Black、Naresh Kumar

  DOI：10.1016/j.tetlet.2016.10.067

  日期：2016.12

  A two-step procedure for the synthesis of dihydrodibenzonaphthyridine derivatives from benzaldehydes and 2-aminoacetophenones, proceeding through a substituted dihydroquinolone intermediate, is described. The synthetic protocol allows for a versatile and robust coupling method between a range of 2-aminoacetophenones or 2-aminobenzophenones and a selection of substituted dihydroquinolones.

  描述了由苯甲醛和2-氨基苯乙酮合成二氢二苯并萘啶衍生物的两步程序，该程序通过取代的二氢喹诺酮中间体进行。合成规程允许在一系列2-氨基苯乙酮或2-氨基二苯甲酮与选择的取代二氢喹诺酮之间进行灵活多样的偶联。
• An efficient oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones employing ferric chloride hexahydrate–methanol: synthesis of naturally occurring 4-alkoxy-2-arylquinolines
  作者：K. Hemanth Kumar、D. Muralidharan、P.T. Perumal

  DOI：10.1016/j.tetlet.2004.08.144

  日期：2004.10

  A simple, inexpensive and efficient oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones has been carried out by employing FeCl3-6H(2)O-methanol under mild conditions. This method has been investigated for the synthesis of an endothelin receptor antagonist, benzofuro[3,2-b]pyridine core structure. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents
  作者：Gonca TOSUN、Tayfun ARSLAN、Zeynep İSKEFİYELİ、Murat KÜÇÜK、Şengül ALPAY KARAOĞLU、Nurettin YAYLI

  DOI：10.3906/kim-1501-112

  日期：——

  Three new series of 33 quinolone compounds, 2-(2-, 3-, and 4-fluorophenyl)-4-O-alkyl(C$_5-15})$quinolines (7a-k, 8a-k, and 9a-k), were synthesized from 2-(2-, 3-, and 4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (4, 5, and 6) by the reaction of alkyl halides under basic conditions in DMF. The new compounds 7a-k, 8a-k, and 9a-k were synthesized from flavonones 4-6, which can be considered new precursors for quinoline synthesis through a one-step reaction. All the target compounds (7a-k, 8a-k, and 9a-k) were evaluated for their in vitro antimicrobial activity against nine test microorganisms. They showed the most activity against Mycobacterium smegmatis with minimum inhibitory concentrations (MIC) of 62.5-500 $\mu $g/mL, indicating their potential uses as antituberculosis agents. Among them 8a-k (m-fluoride) were the most active compounds against M. smegmatis (MIC, 62.5-125 $\mu $g/mL). The newly synthesized title compounds were also evaluated for their in vitro antioxidant activities using DPPH• radical scavenging and FRAP tests. They showed at a low concentration (mg/mL) a range of SC$_50}$ values of 0.03-12.48 mg/mL (DPPH•) and 0-722 $\mu $M (FRAP), respectively. The antioxidant results of compounds 7a-k, 8a-k, and 9a-k revealed that the length of the alkyl chain was negatively correlated with antioxidant capacity.

  合成了3个系列共33种喹诺酮化合物:2-(2-、3-和4-氟苯基)-4-O-烷基(C$_5-15}$)喹诺啉(7a-k、8a-k和9a-k),由2-(2-、3-和4-氟苯基)-2,3-二氢喹啉-4(1H)-酮(4、5和6)在DMF中用卤代烷在碱性条件下反应制得。新化合物7a-k、8a-k和9a-k由黄酮酮4-6制备,可视为一步反应合成喹诺啉的新前体。所有目标化合物(7a-k、8a-k和9a-k)均对其体外抗菌活性进行了评价,在九种试验微生物中它们对耻垢分枝杆菌的活性最强,最高抑制浓度(MIC)为62.5-500 $\mu g/ mL,表明它们有可能用作抗结核剂。其中8a-k(间氟苯基)对耻垢分枝杆菌的活性最强(MIC, 62.5-125 $\mu g/ mL)。新合成的标题化合物也用DPPH•自由基清除法和FRAP法对其体外抗氧化活性进行了评价。它们在低浓度(mg/mL)下的SC$_50}$值范围分别为0.03-12.48 mg/mL(DPPH•)和0-722 $\mu M$(FRAP)。化合物7a-k、8a-k和9a-k的抗氧化结果表明,烷基链的长度与抗氧化能力负相关。
• Simple and Efficient Synthesis of 2-Aryl-2,3-Dihydroquinolin-4(1<i>H</i>)-ones Using Silica Chloride as a New Catalyst Under Solvent-Free Conditions
  作者：M. Muthukrishnan、M. Mujahid、V. Punitharasu、D. A. Dnyaneshwar

  DOI：10.1080/00397910903097252

  日期：2010.4.12

  A mild, efficient, and high-yielding method for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones from their corresponding 2-amino chalcones using silica chloride (SiO2Cl) under solvent-free conditions is described. A series of 2-aryl-2,3-dihydroquinolin-4(1H)-ones containing both electron-donating and electron-withdrawing substituents were synthesized.

  描述了一种在无溶剂条件下使用氯化硅 (SiO2Cl) 从相应的 2-氨基查耳酮合成 2-芳基-2,3-二氢喹啉-4(1H)-酮的温和、高效和高产的方法. 合成了一系列包含给电子和吸电子取代基的 2-aryl-2,3-dihydroquinolin-4(1H)-ones。