4-methyl-2-(4-nitrophenyl)quinoline | 14365-92-5

• 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: 4-methyl-2-(4-nitrophenyl)quinoline
• 英文别名: 4-methy-2-(4-nitrophenyl)quinoline；4-methyl-2-(4-nitro-phenyl)-quinoline；4-Methyl-2-(4-nitro-phenyl)-chinolin；4-Methyl-2-<4-nitro-phenyl>-chinolin；4-Methyl-2-(4'-nitro-phenyl)-quinoline
• CAS: 14365-92-5
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: KHCYNZSVNWAXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-methyl-2-(4-nitrophenyl)quinoline 在 硫酸 、 溶剂黄146 、 锌 作用下， 生成 4-(4-甲基-喹啉-2-基)-苯酚
  参考文献：
  名称：

  Besthorn; Fischer,O., Chemische Berichte, 1883, vol. 16, p. 69

  摘要：

  DOI：
• 作为产物：
  描述：

  N-<(4-nitrophenyl)methylene>-2-(2-propenyl)benzenamine 在 氧气 、 菲醌 、 magnesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以79%的产率得到4-methyl-2-(4-nitrophenyl)quinoline
  参考文献：
  名称：

  菲醌敏化光催化2-乙烯基芳胺光催化合成多取代喹啉

  摘要：

  可见光激发的 9,10-菲醌 (PQ*) 用作光催化剂，用于通过 2-乙烯基芳基亚胺的电环化合成多取代的喹啉。当 MgCO 3用作 DCM 中的添加剂时，在室温下用蓝色 LED 激发 1 小时后，可得到高达定量的 2,4-二取代喹啉。在实验和 DFT 研究的基础上，我们提出 PQ* 诱导亚胺底物的单电子氧化，从而触发电环化机制。

  DOI：

  10.1021/acs.orglett.1c03934

文献信息

• Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2‐Vinyl Anilines
  作者：Mikko K. Mäkelä、Evgeny Bulatov、Kiia Malinen、Juulia Talvitie、Martin Nieger、Michele Melchionna、Anna Lenarda、Tao Hu、Tom Wirtanen、Juho Helaja

  DOI：10.1002/adsc.202100711

  日期：2021.8.3

  polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The

  氧化活性炭 (oAC) 催化邻乙烯基苯胺和醛形成多取代喹啉。该反应通过缩合、电环化和脱氢以级联方式进行，并提供了范围广泛的具有烷基和/或芳基取代基的喹啉，如 40 个例子所示。无金属催化过程允许合成各种多取代喹啉的异质协议。机理研究表明，oAC 中的酸基和醌基都是催化歧管的组成部分。
• Cu(ii)-promoted three-component coupling sequence for the efficient synthesis of substituted quinolines
  作者：Fuhong Xiao、Wen Chen、Yunfeng Liao、Guo-Jun Deng

  DOI：10.1039/c2ob26484f

  日期：——

  The copper-promoted three-component coupling sequence for substituted quinoline formation from aldehydes, anilines and acetone is described. Various 2-arylquinolines were selectively obtained in good yields under mild conditions. The reaction tolerated a wide range of functionalities.

  铜促进的三组分偶联序列，用于由醛，苯胺和苯胺形成取代的喹啉 丙酮描述。在温和的条件下，以高收率选择性地获得了各种2-芳基喹啉。该反应可耐受多种功能。
• CsxH3−xPW12O40 heteropoly salts catalyzed quinoline synthesis via Friedländer reaction
  作者：Ezzat Rafiee、Fereshte Khajooei Nejad、Mohammad Joshaghani

  DOI：10.1016/j.cclet.2010.09.036

  日期：2011.3

  cesium partially substituted phosphotungstate, CsxH3−xPW12O40 (x = 1.0, 2.0 and 2.5), were synthesized and their catalytic activities were investigated in the synthesis of quinoline. It was shown that catalytic activities of these catalysts correlated to surface acidity and total number of acidic sites. Finally, a series of quinoline derivatives were synthesized with Cs2.5H0.5PW12O40 via the Friedlander

  摘要合成了各种类型的铯部分取代的磷钨酸铯CsxH3-xPW12O40（x = 1.0、2.0和2.5），并研究了它们在喹啉合成中的催化活性。结果表明，这些催化剂的催化活性与表面酸度和酸性位点总数有关。最后，通过Friedlander反应，用Cs2.5H0.5PW12O40高产率合成了一系列喹啉衍生物，并提出了合理的机理。该方法的优点是实验简单，催化剂可重复使用，反应时间短和排除有毒溶剂。
• Application of Heteropoly Acids as Heterogeneous and Recyclable Catalysts for Friedländer Synthesis of Quinolines
  作者：Majid M. Heravi、Negar Mokhtari Haj、Bita Baghernejad、Y. SH. Beheshtia、Fatemeh F. Bamoharram

  DOI：10.1155/2010/743123

  日期：——

  New convenient conditions for the Friedländer synthesis of quinolines are described. Quinolines were readily prepared in the presence of heteropolyacids as heterogeneous and recyclable catalysts in good yields.

  描述了 Friedländer 合成喹啉的新便利条件。在异相和可循环催化剂的存在下，喹啉可以在良好的产率下轻松制备。
• Quantitative Structure Activity Relationship and Biological Activity Studies of 4-Methyl-2-(4-substituted phenyl)quinoline Derivatives
  作者：P.K. Rahangdale、F. Inam、S.S. Chourasia

  DOI：10.14233/ajchem.2018.20811

  日期：——

  Quantitative structure activity relationship (QSAR) studies of some 4-methyl-2-(4-substituted phenyl)quinoline derivatives were carried out to determine their predicted biological activities. Numbers of descriptors were tested to adjudge a quantitative correlation between activity and structural features using training set and test set. Significant correlation was observed between activities and descriptors. The results were interpreted on the basis of linear regression analysis. Experimental antibacterial activities of the test set compounds were determined. The predicted biological activities generated by QSAR model were compared with the experimental antibacterial activities. The concurrence between the predicted and experimental biological activities validates the QSAR model. Thus, it can be concluded that the model under the present investigation can be applied for predicting the unknown biological activities of structurally similar molecules.

  对一些 4-甲基-2-（4-取代苯基）喹啉衍生物进行了定量结构活性关系（QSAR）研究，以确定它们的预测生物活性。使用训练集和测试集测试了描述因子的数量，以判断活性与结构特征之间的定量相关性。结果表明，活性与描述因子之间存在显著的相关性。根据线性回归分析对结果进行了解释。确定了测试集化合物的实验抗菌活性。将 QSAR 模型预测的生物活性与实验抗菌活性进行了比较。预测生物活性与实验生物活性之间的一致性验证了 QSAR 模型。因此，可以得出结论，本研究中的模型可用于预测结构相似分子的未知生物活性。