2-(4-methylphenyl)-6-nitro-4-phenylquinoline | 1285610-49-2

• 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-(4-methylphenyl)-6-nitro-4-phenylquinoline
• 英文别名: 6-nitro-4-phenyl-2-(p-tolyl)quinoline；2-p-tolyl-4-phenyl-6-nitroquinoline；6-nitro-4-phenyl-2-p-tolylquinoline
• CAS: 1285610-49-2
• 化学式: C₂₂H₁₆N₂O₂
• 分子量: 340.381
• InChiKey: PTSVVHAPQLSOSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methylphenyl)-6-nitro-4-phenylquinoline 在 palladium 10% on activated carbon 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 12.5h， 以72%的产率得到
  参考文献：
  名称：

  新喹啉染料的简便合成和光物理性质

  摘要：

  本文描述了新的喹啉衍生物的合成，这些化合物一直是有机化学和药物化学领域的长期关注。通过多组分反应（MCR），这是现代合成方法学中的重要工具，它除了具有经济的原子性和选择性外，还可以产生具有良好结构复杂性的产物，从而使人们可以轻松地制备喹啉衍生物。五氯化铌作为路易斯酸促进了反应。随后，使用Pd / C和肼进行了高收率的新氨基喹啉衍生物的合成。喹啉衍生物的光物理研究表明，取代基对光学性质表征的影响是通过吸收和光致发光测量完成的，量子产率高达83％，喹啉主链第6位氨基的存在对于获得这些增加的量子产率至关重要。结果表明，这些分子可能在多种应用中具有潜在用途，并且由于其在光电器件中的广泛应用潜力而引起了人们的广泛关注。

  DOI：

  10.1007/s10895-016-1954-5
• 作为产物：
  描述：

  对甲基苯乙酮 、 2-氨基-5-硝基二苯甲酮 在 三氟乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.2h， 以72%的产率得到2-(4-methylphenyl)-6-nitro-4-phenylquinoline
  参考文献：
  名称：

  Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase

  摘要：

  A series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a-l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol- 3-yl)-6-nitro-4-phenylquinoline (10l; IC50 = 1.98 mu M) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.081

文献信息

• Silver-Catalyzed Oxidative Coupling of Aniline and Ene Carbonyl/Acetylenic Carbonyl Compounds: An Efficient Route for the Synthesis of Quinolines
  作者：Xu Zhang、Xuefeng Xu

  DOI：10.1002/asia.201402742

  日期：2014.11

  An efficient silver‐mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules

  据报道，银介导的苯胺与烯羰基/炔羰基化合物的有效银偶联可合成喹啉。该转化对广泛的底物有效，因此能够扩展杂环骨架上的取代基结构。已经研究了胺上取代基的电子性质。研究发现，同时具有给电子和吸电子取代基的分子是进行这种转化的合适底物，并且以中等至极好的收率获得了预期的产物。
• Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine
  作者：Xu Zhang、Xuefeng Xu、Lintao Yu、Qiang Zhao

  DOI：10.1016/j.tetlet.2014.02.090

  日期：2014.4

  Herein we report simple Bronsted acid-mediated reactions of aldehydes with 2-vinylaniline and biphenyl-2-amine. Ultimately, the useful nitrogen-containing heterocycle derivatives are obtained. The electronic properties of the substituents on the aldehydes and 2-vinylaniline were investigated. It was found that molecules with both electron-donating and -withdrawing substituents were perfectly suitable

  在本文中，我们报道了醛与2-乙烯基苯胺和联苯-2-胺的简单布朗斯台德酸介导的反应。最终，获得了有用的含氮杂环衍生物。研究了醛和2-乙烯基苯胺上取代基的电子性质。已发现具有给电子和吸电子取代基的分子是该转化的完全合适的底物，并且以中等至优异的产率获得了预期的产物。
• Microwave-Promoted Alkynylation-Cyclization of 2-Aminoaryl Ketones: A Green Strategy for the Synthesis of 2,4-Disubstituted Quinolines
  作者：Iraj Mohammadpoor-Baltork、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani、Salma Anvar、Arsalan Mirjafari

  DOI：10.1055/s-0030-1259065

  日期：2010.12

  A series of 2,4-disubstituted quinolines were easily prepared through a one-pot reaction of structurally diverse 2-aminoaryl ketones with various arylacetylenes in the presence of K5CoW12O40˙3H2O as a reusable and environmentally benign catalyst under microwave irradiation and solvent-free conditions.

  一系列2,4-二取代喹啉通过在微波辐射和无溶剂条件下，使用K5CoW12O40·3H2O作为可重复使用的环保催化剂，以结构多样的2-氨基芳基酮与各种芳基炔烃进行一锅反应，轻松制备。
• Efficient and environmentally-benign three-component synthesis of quinolines and bis-quinolines catalyzed by recyclable potassium dodecatungstocobaltate trihydrate under microwave irradiation
  作者：Salma Anvar、Iraj Mohammadpoor-Baltork、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani、Ahmad Reza Khosropour、Reza Kia

  DOI：10.1039/c2ra20639k

  日期：——

  Microwave-assisted one-pot three-component reaction between aromatic amines, aromatic aldehydes and phenylacetylene is accomplished efficiently in the presence of catalytic amounts of potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O) to afford the corresponding quinolines and bis-quinolines in excellent yields. Selective conversion of aromatic aldehyde and also arylacetylene to their corresponding

  微波辅助一锅三元反应的芳香胺，芳香醛和 苯乙炔在催化量的十二水合十二碳五烯酸钴钾三水合物（K 5 CoW 12 O 40 ·3H 2 O）的存在下有效地完成了上述反应，从而以优异的产率提供了相应的喹啉和双喹啉。在脂肪族醛和烷基乙炔的存在下，芳族醛以及芳基乙炔分别选择性地转化为它们相应的喹啉可以被认为是该方法的显着优点，并且使其成为合成喹啉衍生物的有用且有吸引力的方法。该催化剂可以重复使用数个循环而不会显着降低其催化活性。
• Synthesis and evaluation of 2-(1H-indol-3-yl)-4-phenylquinolines as inhibitors of cholesterol esterase
  作者：Gisela C. Muscia、Stephanie Hautmann、Graciela Y. Buldain、Silvia E. Asís、Michael Gütschow

  DOI：10.1016/j.bmcl.2014.01.081

  日期：2014.3

  A series of 2-(substituted) phenyl and 2-indolyl quinoline derivatives (10a-l) was synthesized by an efficient microwave-assisted, trifluoroacetic acid-catalyzed, solvent-free method. Evaluation of the inhibitory activity led to the identification of two quinoline inhibitors of cholesterol esterase. 2-(1H-Indol- 3-yl)-6-nitro-4-phenylquinoline (10l; IC50 = 1.98 mu M) was characterized as a mixed-type inhibitor with a pronounced competitive binding mode. (C) 2014 Elsevier Ltd. All rights reserved.