4-(p-tolyl)quinoline | 302357-89-7

• 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-(p-tolyl)quinoline
• 英文别名: 4-(4-Methylphenyl)quinoline
• CAS: 302357-89-7
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: USNIKPHVMLQFDK-UHFFFAOYSA-N

物化性质

• 熔点：
  90.5-91.5 °C
• 沸点：
  364.6±21.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(p-tolyl)quinoline 在 乙基溴化镁 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 N-butyl-2-methyl-4-(4-methylphenyl)-2H-quinoline-1-carboxamide
  参考文献：
  名称：

  A new synthesis of functionalized imidazol-2-ones

  摘要：

  The novel preparation of imidazol-2-ones in four steps from quinolines via an oxidative ring rearrangement is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01070-4
• 作为产物：
  描述：

  (Z)-3-(4-methylphenyl)-3-(2-nitrophenyl)prop-2-enal 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以95%的产率得到4-(p-tolyl)quinoline
  参考文献：
  名称：

  New protocols for the synthesis of 3,4-annulated and 4-substituted quinolines from β-bromo-α,β-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2-bromoacetanilide

  摘要：

  The palladium[0]-mediated Ullmann cross-coupling of readily available beta-bromo-alpha,beta-unsaturated aldehydes of the general form 2 with 1-bromo-2-nitrobenzene (3, X = Br) delivers products, 4, that undergo reductive cyclization to novel quinolines (5) upon exposure to indium in aqueous ammonium chloride or to Raney-nickel in the presence of dihydrogen. Analogous cross-coupling of 2-bromoacetanilide (6) with 2 affords products of type 7 that undergo in situ and K2CO3-mediated cyclization to give the same types of quinolines (5). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.078

文献信息

• Direct C−H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids
  作者：Ian B. Seiple、Shun Su、Rodrigo A. Rodriguez、Ryan Gianatassio、Yuta Fujiwara、Adam L. Sobel、Phil S. Baran

  DOI：10.1021/ja1066459

  日期：2010.9.29

  A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method

  已经开发了多种缺电子杂环与芳基硼酸的直接芳基化。这种新反应在室温下很容易使用廉价试剂进行：在过硫酸盐助氧化剂存在下催化硝酸银（I）。杂环和硼酸偶联伙伴的范围很广，敏感的官能团是可以容忍的。这种方法允许快速访问传统方法更难以访问的各种芳基化杂环。
• Iron-Catalyzed Direct C-H Arylation of Heterocycles and Quinones with Arylboronic Acids
  作者：Arghya Deb、Srimanta Manna、Arun Maji、Uttam Dutta、Debabrata Maiti

  DOI：10.1002/ejoc.201300743

  日期：2013.8

  The arylation of C–H bonds to generate heteroaryl–aryl (Het–Ar) and arylated quinone (Quin–Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het–Ar and Quin–Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic

  C-H键的芳基化生成杂芳基-芳基（Het-Ar）和芳基化醌（Quin-Ar）化合物在合成化学中实现可持续目标方面受到了极大的关注。尽管取得了重大进展，广泛的 Het-Ar 和 Quin-Ar 衍生物的芳基化仍然是一项具有挑战性的任务。在本文中，在催化量的廉价 Fe(NO3)3 存在下，使用芳基硼酸将各种杂环芳基化。C-芳基化醌化合物可以通过芳基硼酸与醌或氢醌反应来制备。本方法操作简单，可扩展，不需要杂环或醌的预官能化，并且可以容忍偶联伙伴中的多种官能团。这些品质有望使这种方法对学术和工业用途具有吸引力。
• Aerobic oxidative dehydrogenation of N-heterocycles over OMS-2-based nanocomposite catalysts: preparation, characterization and kinetic study
  作者：Xiuru Bi、Tao Tang、Xu Meng、Mingxia Gou、Xiang Liu、Peiqing Zhao

  DOI：10.1039/c9cy01968e

  日期：——

  aerobic oxidative dehydrogenation of N-heterocycles were examined in detail. Many tetrahydroquinoline derivatives and a broad range of other N-heterocycles could be tolerated by the catalytic system using a biomass-derived solvent as a reaction medium. Newly generated mixed crystal phases, noticeably enhanced surface areas and labile lattice oxygen of the OMS-2-based nanocomposite catalysts might contribute

  首次制备了掺有钨的基于OMS-2的纳米复合材料，并详细研究了它们在N杂环的好氧氧化脱氢中的显着增强的催化活性和可回收性。使用生物质衍生的溶剂作为反应介质的催化体系可以耐受许多四氢喹啉衍生物和各种其他N-杂环。OMS-2基纳米复合催化剂的新生成的混合晶体相，显着增加的表面积和不稳定的晶格氧可能有助于其出色的催化性能。此外，进行了广泛的动力学研究，得出的结论是1,2,3,4-四氢喹啉的脱氢是一级反应，表观活化能为29.66 kJ mol -1。
• Time-Resolved EPR Revealed the Formation, Structure, and Reactivity of N<i>-</i>Centered Radicals in an Electrochemical C(sp³)–H Arylation Reaction
  作者：Yichang Liu、Biyin Shi、Zhao Liu、Renfei Gao、Cunlong Huang、Hesham Alhumade、Shengchun Wang、Xiaotian Qi、Aiwen Lei

  DOI：10.1021/jacs.1c09341

  日期：2021.12.15

  over the past few years, while a vast majority of the reactions proceed through a radical pathway. Understanding the properties of radical intermediates is crucial in the mechanistic study of electrochemical transformations and will be beneficial for developing new reactions. Nevertheless, it is rather difficult to determine the “live” radical intermediates due to their high reactivity. In this work

  电化学合成在过去几年中得到了迅速发展，而绝大多数反应通过自由基途径进行。了解自由基中间体的性质对于电化学转化的机理研究至关重要，并将有利于开发新的反应。然而，由于它们的高反应性，很难确定“活性”自由基中间体。本工作利用时间分辨电子顺磁共振(EPR)技术在电化学条件下直接研究了磺胺N-中心自由基的形成和结构。在 EPR 结果的支持下，N -中心自由基作为氢原子转移 (HAT) 方法中的介质已被讨论。随后，这些机理研究结果已成功用于发现未活化的 C(sp 3 )-H 芳基化反应。动力学实验表明，速率决定步骤是磺胺类药物的阳极氧化。
• A Manganese-Catalyzed Cross-Coupling Reaction
  作者：Magnus Rueping、Winai Ieawsuwan

  DOI：10.1055/s-2007-968013

  日期：2007.2

  A manganese-catalyzed cross-coupling reaction of ­heterocyclic chlorides with aryl- as well as alkylmagnesium halides has been developed. The reaction provides a variety of heterocyclic compounds under mild and practical reaction conditions using low amounts of manganese chloride as catalyst.

  开发了一种由锰催化的杂环氯化物与芳基及烷基镁卤化物的交叉偶联反应。该反应在温和且实用的条件下，使用少量锰氯化物作为催化剂，生成多种杂环化合物。