10-(4-chlorobenzoyl)benzo[h]quinoline | 1415419-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 10-(4-chlorobenzoyl)benzo[h]quinoline
• CAS: 1415419-91-8
• 化学式: C₂₀H₁₂ClNO
• 分子量: 317.774
• InChiKey: LEKUFEYFCYHYKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)苯并噁唑; 2-(4-甲基苯基)-1,3-苯并噁唑 、 4-氯苯甲醛 在 叔丁基过氧化氢 、 palladium diacetate 、 三苯基膦 作用下， 以 氯苯 为溶剂， 反应 8.0h， 以96%的产率得到10-(4-chlorobenzoyl)benzo[h]quinoline
  参考文献：
  名称：

  Palladium-catalyzed ortho-acylation of 2-arylbenzoxazoles

  摘要：

  An efficient and facile catalytic protocol for benzoxazole-directed ortho-acylation of 2-arylbenzoxazoles has been described using aldehydes as the easily accessible acyl source. This catalytic system was performed in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant in chlorobenzene, affording the acylated 2-arylbenzoxazoles in moderate to good yields. The acylation exhibited high regioselectivity for the substrates containing a meta-substituent in the benzene ring and typically occurred at the less sterically hindered ortho-C-H bond of the directing group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.033

文献信息

• Palladium-catalyzed ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles using arylmethyl alcohols as the acyl source
  作者：Qian Zhang、Fan Yang、Yangjie Wu

  DOI：10.1016/j.tet.2013.04.052

  日期：2013.6

  A facile and efficient way for the synthesis of the acylated 2-arylbenzoxazoles and 2-arylbenzothiazoles by heterocycle-directed ortho-acylation was developed. This reaction was performed in chlorobenzene, using arylmethyl alcohols and tert-butyl hydroperoxide (TBHP) as the easily accessible acyl source and the oxidant, respectively, affording the desired products in moderate to good yields.

  开发了一种简便有效的方法，该方法通过杂环导向的邻位酰化反应来合成酰化的2-芳基苯并恶唑和2-芳基苯并噻唑。该反应在氯苯中进行，分别使用芳基甲醇和叔丁基过氧化氢（TBHP）作为容易获得的酰基源和氧化剂，以中等至良好的收率提供所需的产物。
• Pd(<scp>ii</scp>)-catalysed o-aroylation of directing arenes using terminal aryl alkenes and alkynes
  作者：Nilufa Khatun、Arghya Banerjee、Sourav K. Santra、Ahalya Behera、Bhisma K. Patel

  DOI：10.1039/c4ra11014e

  日期：——

  A substrate-directed Pd-catalysed o-aroylation strategy has been demonstrated using new aroyl surrogates viz. terminal aryl alkenes and alkynes in the presence of TBHP. By a subtle change in catalyst from Cu to Pd, a differential selectivity is observed. While terminal aryl alkenes/alkynes in the presence of Cu/TBHP are reported to act as o-aryloxy (ArCOO–) sources, the use of Pd/TBHP installs an aroyl (ArCO–) group at the ortho position with respect to the directing arenes.

  已证明了一种基于底物导向的Pd催化o-芳酰化策略，使用了新的芳酰替代物，即末端芳烃烯和炔烃，且在TBHP的存在下进行。通过将催化剂从Cu更改为Pd，观察到了选择性的差异。当末端芳烃烯/炔烃在Cu/TBHP的存在下时，报告称其作为o-芳氧基（ArCOO–）的来源，而使用Pd/TBHP则在与导向芳烃相对的邻位引入芳酰基（ArCO–）。
• Monodisperse CuPd alloy nanoparticles as efficient and reusable catalyst for the C (sp ² )–H bond activation
  作者：Fei Huang、Feifan Wang、Qiyan Hu、Lin Tang、Dongping Xu、Yang Fang、Wu Zhang

  DOI：10.1002/aoc.6236

  日期：2021.7

  activation of C–H bonds is very important for the construction of a variety of biologically active molecules. Supported alloy nanoparticles are of great interest in various catalytic applications due to the synergistic effects between different metals. Here, well-dispersed CuPd alloy nanoparticles supported on reduced graphene oxide (rGO) were synthesized and found to be highly efficient and recyclable

  金属催化的 C-H 键选择性活化对于构建各种生物活性分子非常重要。由于不同金属之间的协同效应，负载型合金纳米粒子在各种催化应用中引起了极大的兴趣。在这里，合成了负载在还原氧化石墨烯 (rGO) 上的分散良好的 CuPd 合金纳米粒子，并发现它是螯合辅助 C (sp 2 )-H 键活化的高效且可回收的催化剂。芳族酮或酯是通过 2-芳基吡啶与醇或酸之间的交叉脱氢偶联 (CDC) 反应合成的。此外，催化剂回收使用五次，活性没有明显降低。
• Ag1Pd1-rGO nanocomposite as recyclable catalyst for CDC reactions of 2-arylpyridines with aldehydes
  作者：Qiyan Hu、Xiaowang Liu、Fei Huang、Feifan Wang、Qian Li、Wu Zhang

  DOI：10.1016/j.catcom.2018.05.007

  日期：2018.7

  Ag1Pd1 nanoparticle-reduced graphene oxide (Ag1Pd1-rGO) nanocomposite was used as an efficient catalyst for the synthesis of aromatic ketones via cross dehydrogenative coupling (CDC) reactions of 2-arylpyridines with aldehydes. The catalyst can be reused for 5 cycles without significantly losing its catalytic activity. On the basis of the obtained experimental evidence, we proposed a possible mechanism

  Ag 1 Pd 1纳米粒子还原的氧化石墨烯（Ag 1 Pd 1 -rGO）纳米复合材料被用作通过2-芳基吡啶与醛的交叉脱氢偶联（CDC）反应合成芳族酮的有效催化剂。催化剂可重复使用5个循环，而不会明显丧失其催化活性。在获得的实验证据的基础上，我们提出了一种多相催化的可能机制。我们发现，负载型催化剂表现出一系列好处，包括非凡的催化活性，高可重复使用性和对各种底物的显着耐受性。
• Benzyl bromides as aroyl surrogates in substrate directed Pd catalysed o-aroylation
  作者：Ahalya Behera、Wajid Ali、Srimanta Guin、Nilufa Khatun、Prakash R. Mohanta、Bhisma K. Patel

  DOI：10.1039/c5ra03836g

  日期：——

  An oxidative cross-coupling between directing substrates and benzyl bromides leading to o-aroylation has been achieved using TBHP/NMO, and Pd(ii).

  直接给你结果：

  使用TBHP/NMO和Pd(ii)，实现了导向基质和苄溴化物之间的氧化交叉偶联，从而实现了o-芳酰化。