ethyl 4-(4-fluorophenyl)-6-methoxyquinoline-2-carboxylate | 1174133-27-7

• 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: ethyl 4-(4-fluorophenyl)-6-methoxyquinoline-2-carboxylate
• CAS: 1174133-27-7
• 化学式: C₁₉H₁₆FNO₃
• 分子量: 325.339
• InChiKey: FZHRRFNOTWSEBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟苯乙炔 、 ethyl (4-methoxyphenylimino)acetate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以81%的产率得到ethyl 4-(4-fluorophenyl)-6-methoxyquinoline-2-carboxylate
  参考文献：
  名称：

  A Simple and Convenient Copper-Catalyzed Tandem Synthesis of Quinoline-2-carboxylates at Room Temperature

  摘要：

  We developed a simple and convenient copper-catalyzed method for the synthesis of quinoline-2-carboxylate derivatives through sequential intermolecular addition of alkynes onto imines and subsequent intramolecular ring closure by arylation. The efficiency of this system allowed the reactions to be carried out at room temperature.

  DOI：

  10.1021/jo901101v

文献信息

• Visible-Light-Induced Photocatalytic Aerobic Oxidative C_sp3–H Functionalization of Glycine Derivatives: Synthesis of Substituted Quinolines
  作者：Xiaorong Yang、Liqi Li、Ying Li、Yuan Zhang

  DOI：10.1021/acs.joc.6b02683

  日期：2016.12.16

  with unactivated alkenes has been accomplished. This visible light-driven protocol has been successfully applied to a broad scope of glycine esters and simple alkenes, giving rise to diverse substituted quinoline derivatives in 18–84% yield under mild (at room temperature under air atmosphere) and operationally simple reaction conditions.

  甘氨酸酯与未活化烯烃的可见光诱导的光催化需氧氧化脱氢偶联/芳构化串联反应已经完成。这种可见光驱动的方案已成功地应用于广泛的甘氨酸酯和简单的烯烃，在温和的条件下（在室温下，在大气中）和操作简单的反应条件下，以18-84％的产率产生了各种取代的喹啉衍生物。
• Synthesis and anti-toxoplasmosis activity of 4-arylquinoline-2-carboxylate derivatives
  作者：James McNulty、Ramesh Vemula、Claudia Bordón、Robert Yolken、Lorraine Jones-Brando

  DOI：10.1039/c3ob41539b

  日期：——

  A one-step synthesis of 4-arylquinoline-2-carboxylates along with their antiprotozoal activity against the pathogenic parasite Toxoplasma gondii is reported. Mechanistic insights into the role of Lewis acid (silver triflate) versus Bronsted acid (triflic acid) catalysis are revealed clarifying aspects of the mechanism of the quinoline synthesis.

  报道了一种一步合成4-芳基喹啉-2-羧酸酯及其对病原寄生虫弓形虫的抗原虫活性的方法。揭示了路易斯酸（三氟甲磺酸银）与布朗斯特酸（三氟甲磺酸）催化作用在喹啉合成机制中的作用，澄清了相关机制的方面。
• One‐Pot Synthesis of Highly Substituted Quinolines in Aqueous Medium and Its Application for the Synthesis of Azalignans
  作者：Amrendra Kumar、Ramanand Prajapati、Ruchir Kant、Tadigoppula Narender

  DOI：10.1002/ejoc.202000906

  日期：2020.9.14

  A one‐pot synthesis of highly substituted quinolines is reported. The sequence starts with the C(sp3)‐H functionalization of α‐amino ketone derivatives, glycine esters, or glycine amide in the presence of iodine. Subsequently, a nucleophilic substitution with alkynes or alkynyl esters takes place. An aerobic oxidative aromatization in water with sodium dodecyl sulfate (SDS) as surfactant gives the

  据报道一锅法合成高度取代的喹啉。该序列始于在碘存在下α-氨基酮衍生物，甘氨酸酯或甘氨酸酰胺的C（sp 3）-H官能化。随后，用炔烃或炔基酯进行亲核取代。以十二烷基硫酸钠（SDS）为表面活性剂在水中进行好氧氧化芳构化，喹啉的收率中等至良好。
• A Simple and Convenient Copper-Catalyzed Tandem Synthesis of Quinoline-2-carboxylates at Room Temperature
  作者：He Huang、Hualiang Jiang、Kaixian Chen、Hong Liu

  DOI：10.1021/jo901101v

  日期：2009.8.7

  We developed a simple and convenient copper-catalyzed method for the synthesis of quinoline-2-carboxylate derivatives through sequential intermolecular addition of alkynes onto imines and subsequent intramolecular ring closure by arylation. The efficiency of this system allowed the reactions to be carried out at room temperature.