3-nitroquinoline | 12408-11-6

• 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: 3-nitroquinoline
• 英文别名: 3-Nitro-chinolin
• CAS: 12408-11-6
• 化学式: C₉H₆N₂O₂
• mdl: MFCD00956379
• 分子量: 174.159
• InChiKey: ZXVRNZRQQRBDLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-nitroquinoline 在 双氧水 、 溶剂黄146 作用下， 生成 3-硝基-喹啉1-氧化物
  参考文献：
  名称：

  Landquist, Journal of the Chemical Society, 1956, p. 1885

  摘要：

  DOI：
• 作为产物：
  描述：

  3-anilino-2-nitro-acrylaldehyde 在 zinc(II) chloride 作用下， 生成 3-nitroquinoline
  参考文献：
  名称：

  THE ERGOT ALKALOIDS. XX. THE SYNTHESIS OF DIHYDRO-dl-LYSERGIC ACID. A NEW SYNTHESIS OF 3-SUBSTITUTED QUINOLINES

  摘要：

  DOI：

  10.1021/jo01177a014

文献信息

• <i>ipso</i>-Nitration of Arylboronic Acids with Bismuth Nitrate and Perdisulfate
  作者：Srimanta Manna、Soham Maity、Sujoy Rana、Soumitra Agasti、Debabrata Maiti

  DOI：10.1021/ol300325t

  日期：2012.4.6

  An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.

  的有效和一锅合成法本位的芳基硼酸-nitration已经研制成功。高效，普遍适用性以及包括杂环和官能团在内的更大的底物范围使该方法具有优势。由于其简单性，我们期望在合成中找到该方法的应用。
• Polymethylhydrosiloxane derived palladium nanoparticles for chemo- and regioselective hydrogenation of aliphatic and aromatic nitro compounds in water
  作者：Dandu Damodara、Racha Arundhathi、T. Venkata Ramesh Babu、Margaret K. Legan、Hephzibah J. Kumpaty、Pravin R. Likhar

  DOI：10.1039/c4ra01333f

  日期：——

  unsaturated, aromatic and heteroaromatic nitro compounds into their corresponding amines has been achieved with highly efficient polysiloxane-stabilised “Pd” nanoparticles on NAP-magnesium oxide supports using an environmentally friendly hydrogenating agent, polymethylhydrosiloxane [PMHS] in water. Highly stable and active Pd nanoparticles were prepared by the reduction of NAP-Mg-PdCl4 with PMHS, which serves

  通过使用环保的氢化剂聚甲基氢硅氧烷，在NAP-氧化镁载体上高效聚硅氧烷稳定的“ Pd”纳米颗粒，已经实现了将多种脂族，不饱和，芳族和杂芳族硝基化合物进行化学和区域选择性加氢成相应的胺的作用。 [PMHS]在水中。通过还原NAP-Mg-PdCl 4制备高度稳定且活性高的Pd纳米颗粒用作还原剂和封端剂的PMHS。在NAP-MgO催化剂上分散良好的钯纳米颗粒在二硝基苯氢化成相应的硝基苯胺中也显示出极好的区域选择性。该催化剂在氢化反应期间具有抗烧结的高耐久性，并且可以在不损失其活性的情况下重复使用。
• Nickel Nanoparticles as Efficient Catalyst for Electron Transfer Reactions
  作者：Puran Singh Rathore、Rajesh Patidar、Sonika Rathore、Sonal Thakore

  DOI：10.1007/s10562-013-1168-2

  日期：2014.3

  was investigated in some electron transfer reactions. The nanoparticles brought about rapid room temperature reduction of a number of nitro aromatics in an aqueous medium with high chemoselectivity and also helped to speed up redox reaction of Fe(CN)6−3 and S2O3−2. In addition, interesting results were obtained for microwave assisted decolourization of azo dye. The reactions were monitored through UV–Vis

  在一些电子转移反应中研究了镍纳米颗粒的催化效率。纳米粒子在室温下以高化学选择性在水性介质中快速还原许多硝基芳烃，还有助于加速 Fe(CN)6-3 和 S2O3-2 的氧化还原反应。此外，偶氮染料的微波辅助脱色也获得了有趣的结果。通过紫外-可见光谱监测反应。本研究具有催化剂和水性介质可重复使用性的额外优势。最终目标是评估低成本纳米催化剂在水性条件下进行电子转移反应的适用性。图形摘要
• Selective Deoxygenation of Heteroaromatic N-Oxides with Olefins Catalyzed by Ruthenium Porphyrin.
  作者：Hiroshi NAKAGAWA、Tsunehiko HIGUCHI、Kazuya KIKUCHI、Yasuteru URANO、Tetsuo NAGANO

  DOI：10.1248/cpb.46.1656

  日期：——

  A new convenient method of deoxygenation of heteroaromatic N-oxides is described. Ruthenium prophyrin was used as a catalyst and this method expressed high yields for o-substituted pyridine N-oxides, quinoline N-oxide derivatives, acridine N-oxide, etc. under mild conditions. Moreover, nitro-, benzyloxy-, and ketone carbonyl groups, which can be affected by the usual deoxygenation methods such as catalytic hydrogenation or borane reduction, were retained.

  报道了一种新的方便的去氧方法，用于杂芳香族N-氧化物的去氧。该方法采用钌卟啉作为催化剂，在温和条件下表现出对邻取代吡啶N-氧化物、喹啉N-氧化物衍生物、吖啶N-氧化物等的高产率。此外，硝基、苄氧基和酮羰基等在传统去氧方法（如催化氢化或硼烷还原）可能受到影响的基团，在此方法中得以保留。
• Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
  作者：Sourajit Bera、Atanu Bera、Debasis Banerjee

  DOI：10.1021/acs.orglett.0c02271

  日期：2020.8.21

  Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies

  本文中，提出了五元和六元N-杂环的有效且选择性的镍催化的脱氢。该转化在烷基，烷氧基，氯，游离羟基和伯胺，内部和末端烯烃，三氟甲基和酯官能团的存在下发生。证明了重要配体和抗疟药奎宁的合成。机理研究表明，环状亚胺是该逐步转化的关键中间体。