2-(pyridin-2-yl)quinolin-4(1H)-one | 110802-13-6

• 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-(pyridin-2-yl)quinolin-4(1H)-one
• 英文别名: 2-(Pyridin-2-YL)quinolin-4-OL；2-pyridin-2-yl-1H-quinolin-4-one
• CAS: 110802-13-6
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: WBSMQNXHMYQUIO-UHFFFAOYSA-N

物化性质

• 沸点：
  450.2±40.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 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：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(pyridin-2-yl)quinolin-4(1H)-one 、 Langlois reagent 在 Graphite 、 tert-butylammonium hexafluorophosphate(V) 、 铂 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以73%的产率得到2-(pyridin-2-yl)-3-trifluoromethylquinolin-4(1H)-one
  参考文献：
  名称：

  喹啉酮的无金属电化学氧化三氟甲基化/ C（sp 2）H功能化

  摘要：

  描述了在无金属催化和无氧化剂条件下喹啉酮的电化学直接三氟甲基化。通过使用该方法，以中等收率获得了一系列2-芳基-3-三氟甲基喹啉-4（1 H）-one。通过使用丁基化羟基甲苯（BHT）作为自由基阻滞剂，最初捕获了BHT-CF 3的加合物，证实了该反应是自由基机理。基于捕获自由基和循环伏安法（CV）的结果，提出了一种反应机理。

  DOI：

  10.1016/j.tetlet.2020.152226
• 作为产物：
  描述：

  2-吡啶甲酰胺 在 5A molecular sieve sodium hydroxide 、 potassium phosphate 、 copper(l) iodide 、 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 43.0h， 生成 2-(pyridin-2-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

• Synthesis of 4-Quinolones via Cyclocondensation of Substituted ortho-Amidoacetophenones: A Refit to the Camps Cyclization by Applying Trimethylsilyl Trifluoromethanesulfonate/Triethylamine
  作者：Hans-Ulrich Reissig、Christian Eidamshaus、Therese Triemer

  DOI：10.1055/s-0030-1260198

  日期：2011.10

  A modification of the classical Camps cyclization is described. A series of substituted 4-quinolone derivatives is prepared via trimethylsilyl trifluoromethanesulfonate/triethylamine induced cyclocondensation of substituted ortho-amidoacetophenones. The process shows a broad substrate scope and allows selective preparation of 2-aryl- and 2-alkyl-substituted 4-quino­lones. Enantiopure starting materials react without loss of optical purity using the modified conditions. Subsequent transformations of the products involving preparation of a 4-quinolyl nonaflate and O-selective methylation are also described.

  本文描述了一种经典Camps环化反应的改进方法。通过三甲基硅基三氟甲磺酸酯/三乙胺引发的取代邻氨基乙酰苯酮的环化缩合反应，制备了一系列取代的4-喹啉酮衍生物。该过程具有广泛的底物适用范围，并能选择性地制备2-芳基和2-烷基取代的4-喹啉酮。使用改进的条件，手性纯的起始材料反应后光学纯度无损失。还描述了产物的后续转化，包括制备4-喹啉基壬二酸盐和O-选择性甲基化反应。
• Reductive Cyclization of <i>o</i>-Nitrophenyl Propargyl Alcohols:  Facile Synthesis of Substituted Quinolines
  作者：Matthew J. Sandelier、Philip DeShong

  DOI：10.1021/ol0710921

  日期：2007.8.1

  Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed by acid-catalyzed Meyer-Schuster rearrangement gave 2-substituted and 2,4-disubstituted quinolines, respectively. Tertiary propargyl alcohols gave excellent yields of the quinoline derivative, while the yields of quinolines were slightly reduced when secondary propargyl alcohol derivatives were utilized.

  还原仲和叔邻硝基苯基炔丙基醇，然后进行酸催化的Meyer-Schuster重排，分别得到2-取代的和2,4-二取代的喹啉。叔炔丙醇给出了优异的喹啉衍生物产率，而当使用仲炔丙醇衍生物时，喹啉的产率略有​​降低。
• Supported palladium-catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes to access quinolin-4(1H)-ones
  作者：Jian-Shu Wang、Chenyu Li、Jun Ying、Tiefeng Xu、Wangyang Lu、Chuan-Ying Li、Xiao-Feng Wu

  DOI：10.1016/j.jcat.2022.02.026

  日期：2022.4

  palladium supported on graphitic carbon nitride (Pd/g-CN) catalyzed carbonylative cyclization of 2-bromonitrobenzenes and alkynes has been developed for the expedite construction of quinolin-4(1)-one scaffolds. By using a low loading heterogeneous palladium catalyst, Mo(CO) as both the CO surrogate and the reductant, and nitroarenes as the nitrogen source, the reaction proceeded well to give a variety

  开发了一种负载于石墨氮化碳 (Pd/g-CN) 上的钯催化 2-溴硝基苯和炔烃的羰基环化，用于加快构建 quinolin-4(1)-one 支架。通过使用低负载量的多相钯催化剂、Mo(CO)作为CO替代物和还原剂、硝基芳烃作为氮源，反应进展顺利，得到了多种从良好到优异的喹啉-4(1)-酮。产量。
• Synthesis of Novel Pyrazolines, Their Boron-Fluorine Complexes, and Investigation of Antibacterial, Antioxidant, and Enzyme Inhibition Activities
  作者：Nuran Kahriman、Zeynep Haşimoğlu、Vildan Serdaroğlu、Fatih Şaban Beriş、Burak Barut、Nurettin Yaylı

  DOI：10.1002/ardp.201600285

  日期：2017.2

  New 3,5‐disubstituted‐2‐pyrazoline derivatives (4–6), their boron‐fluorine complexes (boron (3‐(2′‐aminophenyl),5‐(2′‐/3′‐/4′‐pyridyl)pyrazoline, BOAPPY) (7–9) and boron 1,2′‐diazaflavone complex (BODAF) (11) were synthesized starting from azachalcones (1–3) to diazaflavone (10), respectively. Biological evaluation of compounds 4–9 and 11 showed remarkable antioxidant, antibacterial, and acetylcholinesterase

  新的 3,5-二取代-2-吡唑啉衍生物（4-6），它们的硼-氟配合物（硼（3-（2'-氨基苯基），5-（2'-/3'-/4'-吡啶基）吡唑啉、BOAPPY) (7-9) 和硼 1,2'-二氮杂黄酮复合物 (BODAF) (11) 分别从氮杂查耳酮 (1-3) 到二氮杂黄酮 (10) 合成。化合物 4-9 和11 显示出显着的抗氧化、抗菌和乙酰胆碱酯酶和酪氨酸酶抑制活性。所有新合成的化合物 4-9 和 11 显示出可观的抗菌作用，最小抑制浓度在 4.7-150 μg/mL 范围内。
• Development of <i>N</i>-Methyl-(2-arylquinolin-4-yl)oxypropanamides as Leads to PET Radioligands for Translocator Protein (18 kDa)
  作者：Chad Brouwer、Kimberly Jenko、Sami S. Zoghbi、Robert B. Innis、Victor W. Pike

  DOI：10.1021/jm5007947

  日期：2014.7.24

  Translocator protein (18 kDa), known as TSPO, is a recognized biomarker of neuroinflammation. Radioligands with PET accurately quantify TSPO in neuroinflammatory conditions. However, the existence of three human TSPO genotypes that show differential affinity to almost all useful TSPO PET radioligands hampers such studies. There is an unmet need for genotype-insensitive, high-affinity, and moderately lipophilic TSPO ligands that may serve as leads for PET radioligand development. To address this need, we varied the known high-affinity TSPO ligand (l)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide in its aryl scaffold, side chain tether, and pendant substituted amido group while retaining an N-methyl group as a site for labeling with carbon-11. From this effort, oxygen-tethered N-methyl-aryloxypropanamides emerged as new high-affinity TSPO ligands with attenuated lipophilicity, including one example with attractive properties for PET radioligand development, namely N-methyl-N-phenyl-2-[2-(pyridin-2-yl)quinolin-4-yl]oxy}propanamide (22a; rat K-i = 0.10 nM; human TSPO genotypes K-i = 1.4 nM; clogD = 4.18).