7-chloro-4-(4-chlorophenyl)quinoline | 1318249-22-7

• 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: 7-chloro-4-(4-chlorophenyl)quinoline
• CAS: 1318249-22-7
• 化学式: C₁₅H₉Cl₂N
• 分子量: 274.149
• InChiKey: NQJXOJBGSPSLKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-bis(4-chlorophenyl)acrylaldehyde 在 吡啶 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 盐酸羟胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.17h， 生成 7-chloro-4-(4-chlorophenyl)quinoline
  参考文献：
  名称：

  酰基肟的可见光促进亚甲基基自由基形成：吡啶，喹啉和菲啶的统一方法

  摘要：

  已经建立了涉及可见光诱导的亚胺基自由基形成的统一策略，用于从酰基肟中构建吡啶，喹啉和菲啶。用FAC - [的Ir（ppy）3 ]作为催化剂photoredox，酰基肟通过1e中转化-还原成亚氨基自由基中间体，然后行分子内均裂芳族取代（HAS），得到含有N-芳烃其中。这些反应在室温下以宽范围的底物以高收率进行。这种可见光诱导的亚胺基自由基形成策略已成功地应用于五步精简合成苯并[ c ]菲啶生物碱。

  DOI：

  10.1002/anie.201411342

文献信息

• Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
  作者：Vladyslav Smyrnov、Bastian Muriel、Jerome Waser

  DOI：10.1021/acs.orglett.1c01775

  日期：2021.7.16

  hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34–81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the

  我们报告了在可见光照射下使用环丙烯和叠氮苯并苯并唑酮 (ABZ) 高价碘试剂作为叠氮自由基源合成喹啉。以 34-81% 的产率获得了多取代的喹啉产品。该反应对 3-三氟甲基环丙烯最有效，得到有价值的 4-三氟甲基喹啉。转化可能是通过在环丙烯双键上添加叠氮基形成的亚胺基环化，然后开环和断裂来进行的。
• A Mild Palladium-Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids
  作者：Wenjie Li、Joe J. Gao、Yongda Zhang、Wenjun Tang、Heewon Lee、Keith R. Fandrick、Bruce Lu、Chris H. Senanayake

  DOI：10.1002/adsc.201100141

  日期：2011.7

  A palladium‐catalyzed cross‐coupling between aryl carboxylates and boronic acids has been achieved for the first time by taking advantage of the enhanced reactivity of quinoline 4‐carboxylates. Also for the first time a Suzuki coupling reaction via a self‐activation of boronic acids without addition of base is described. The reactions proceed under mild conditions (25–65 °C) to give excellent yields

  通过利用喹啉4-羧酸盐增强的反应性，首次实现了芳基羧酸盐与硼酸之间的钯催化交叉偶联。还是首次描述了通过硼酸的自活化而不添加碱的Suzuki偶联反应。反应在温和的条件下（25–65°C）进行，可得到优异的收率，并且可以耐受多种功能。
• Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents
  作者：Valter E. Murie、Paula V. Nicolino、Thiago dos Santos、Guido Gambacorta、Rodolfo H. V. Nishimura、Icaro S. Perovani、Luciana C. Furtado、Leticia V. Costa-Lotufo、Anderson Moraes de Oliveira、Ricardo Vessecchi、Ian R. Baxendale、Giuliano C. Clososki

  DOI：10.1021/acs.joc.1c01521

  日期：2021.10.1

  We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some

  我们已经在温和条件下通过 7-氯喹啉的氧化制备了功能化喹啉库，采用间歇和连续流动条件。制备涉及混合锂镁中间体的产生，这些中间体与不同的亲电试剂反应。混合锂锌试剂允许合成卤化和芳基化衍生物。一些合成的 4-甲醇喹啉显示出有趣的抗增殖特性，它们的羟基是合适的氨基生物电子等排体。我们还报告了光学活性衍生物的两步法。
• Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and <i>O</i>-Acyl Hydroxylamine
  作者：Xiao-De An、Shouyun Yu

  DOI：10.1021/acs.orglett.5b01096

  日期：2015.6.5

  A one-pot synthesis of phenanthridines and quinolines from commercially available or easily prepared aldehydes has been reported. O-(4-Cyanobenzoyl)hydroxylamine was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes catalyzed by Bronsted acid. O-Acyl oximes were then subjected to visible light photoredox catalyzed cyclization via iminyl radicals to furnish aza-arenes. A variety of phenanthridines and quinolines have been prepared assisted by Bronsted acid and photocatalyst under visible light at room temperature with satisfactory yields.