ethyl 6-methoxy-4-(m-tolyl)quinoline-2-carboxylate | 1174133-25-5

• 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 6-methoxy-4-(m-tolyl)quinoline-2-carboxylate
• 英文别名: Ethyl 6-methoxy-4-(3-methylphenyl)quinoline-2-carboxylate
• CAS: 1174133-25-5
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: VTQRBKTYIFNMKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基苯乙炔 、 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83%的产率得到ethyl 6-methoxy-4-(m-tolyl)quinoline-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

• 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。
• Synthesis, and the antioxidant, neuroprotective and P-glycoprotein induction activity of 4-arylquinoline-2-carboxylates
  作者：Jaideep B. Bharate、Abubakar Wani、Sadhana Sharma、Shahi Imam Reja、Manoj Kumar、Ram A. Vishwakarma、Ajay Kumar、Sandip B. Bharate

  DOI：10.1039/c4ob00488d

  日期：——

  An efficient synthesis of 4-arylquinoline-2-carboxylates and their antioxidant, neuroprotective and P-glycoprotein induction activity have been described.

  一种高效合成4-芳基喹啉-2-羧酸酯及其抗氧化、神经保护和P-糖蛋白诱导活性已被描述。
• Visible-light-induced C_sp³–H functionalization of glycine derivatives by cerium catalysis
  作者：Shutao Wang、Yanjie Ye、Yansong Hu、Xu Meng、Zhao Liu、Jiyu Liu、Kuan Chen、Zhengze Zhang、Yuan Zhang

  DOI：10.1039/d2cc07071e

  日期：——

  A Ce(III)-catalyzed, visible-light-induced aerobic oxidative dehydrogenative coupling/aromatization reaction between glycine derivatives and alkenes has been developed, which provides an efficient approach for the synthesis of quinoline derivatives and post-modification of oligopeptides containing glycine residues under mild conditions without the need for external photosensitizers.

  开发了Ce( III )催化、可见光诱导的甘氨酸衍生物与烯烃之间的有氧氧化脱氢偶联/芳构化反应，为喹啉衍生物的合成和含有甘氨酸残基的寡肽的后修饰提供了一种有效的途径。不需要外部光敏剂的温和条件。