ethyl 6-methyl-4-(p-tolyl)quinoline-2-carboxylate | 1174133-34-6

• 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: ethyl 6-methyl-4-(p-tolyl)quinoline-2-carboxylate
• 英文别名: Ethyl 6-methyl-4-(4-methylphenyl)quinoline-2-carboxylate
• CAS: 1174133-34-6
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: WQMYKQYISIXUEU-UHFFFAOYSA-N

物化性质

• 沸点：
  470.7±45.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 在 sodium acetate 、 lithium perchlorate 、 四丁基碘化铵 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 ethyl 6-methyl-4-(p-tolyl)quinoline-2-carboxylate
  参考文献：
  名称：

  N-芳基甘氨酸酯的功能化：电催化访问由n-Bu4NI介导的CC键。

  摘要：

  报道了N-芳基甘氨酸酯的有效电催化官能化。该协议在恒定电流条件下的一个无分隔单元中进行，采用简单，便宜且易于获得的n-Bu4NI作为介体。此外，已证明介导的过程优于直接电化学官能化。

  DOI：

  10.3762/bjoc.14.35

文献信息

• Copper catalysis: One-pot simultaneous synthesis of quinolines and gem-diamine derivatives
  作者：Xing-Meng Li、Li Tang、Zhu-Ming Qian、Yan-Hong He、Zhi Guan

  DOI：10.1016/j.tetlet.2020.152346

  日期：2020.11

  A copper(II)-catalyzed oxidative reaction for the one-pot simultaneous synthesis of quinolines and gem-diamine derivatives from N-arylglycine ethyl esters and enamides is described. In this reaction, the two fragments in an enamide substrate react with the same intermediate generated in situ from an N-arylglycine ethyl ester, respectively, producing two products simultaneously. This reaction has the

  的铜（II）催化的对喹啉和的一锅同时合成的氧化反应宝石从二胺衍生物N-芳基甘氨酸乙基酯和烯酰胺进行说明。在该反应中，酰胺底物中的两个片段分别与由N-芳基甘氨酸乙酯原位生成的同一中间体反应，同时生成两种产物。该反应具有效率高，操作简单和原子经济性高的优点。
• Auto-Oxidative Coupling of Glycine Derivatives
  作者：Congde Huo、Yong Yuan、Mingxia Wu、Xiaodong Jia、Xicun Wang、Fengjuan Chen、Jing Tang

  DOI：10.1002/anie.201406905

  日期：2014.12.1

  The unprecedented title reaction between glycine derivatives and indoles, as well as the auto‐oxidative Povarov/aromatization tandem reaction of glycine derivatives with olefins are described. The reactions were performed in the absence of redox‐active catalysts and chemical oxidants under mild reaction conditions. Only simple organic solvents and air (or O2) were required.

  描述了甘氨酸衍生物和吲哚之间空前的标题反应，以及甘氨酸衍生物与烯烃的自氧化Povarov /芳香化串联反应。反应在温和的反应条件下，在没有氧化还原活性催化剂和化学氧化剂的情况下进行。仅需要简单的有机溶剂和空气（或O 2）。
• Gold-Oxazoline Complex-Catalyzed Cross-Dehydrogenative Coupling of Glycine Derivatives and Alkenes
  作者：Minjie Ni、Yan Zhang、Tingting Gong、Bainian Feng

  DOI：10.1002/adsc.201601066

  日期：2017.3.6

  A gold‐oxazoline complex‐catalyzed dehydrogenative Povarov/oxidation tandem reaction for the synthesis of decorated quinolines has been developed from glycine derivatives and alkenes. The reaction performs under mild reaction conditions in the presence of oxygen as the oxidant and features a broad substrate scope and excellent functional group tolerance.

  利用甘氨酸衍生物和烯烃开发了金恶唑啉配合物催化的脱氢Povarov /氧化串联反应，用于合成修饰的喹啉。该反应在氧气作为氧化剂的存在下，在温和的反应条件下进行，并具有广泛的底物范围和出色的官能团耐受性。
• An economical synthesis of substituted quinoline-2-carboxylates through the potassium persulfate-mediated cross-dehydrogenative coupling of N-aryl glycine derivatives with olefins
  作者：Guoliang Liu、Jiarui Qian、Jing Hua、Feng Cai、Xia Li、Lei Liu

  DOI：10.1039/c5ob02216a

  日期：——

  A practical and economical K2S2O8-mediated oxidative cross-dehydrogenative coupling of N-aryl glycine derivatives with olefins has been established, affording structurally diverse quinoline-2-carboxylates in good to high efficiency. The low cost, negligible toxicity, and ease of handling of K2S2O8 combined with the absence of hazardous byproducts and the easy workup consisting of simple filtration are attractive based on economic and environmental factors.

  一种实用、经济的 K2S2O8 介导的 N-芳基甘氨酸衍生物与烯烃的氧化交叉脱氢偶联方法已经建立，可高效地获得结构多样的喹啉-2-羧酸盐。基于经济和环境因素，K2S2O8 具有成本低、毒性可忽略不计、易于处理、不产生有害副产物以及只需简单过滤等优点。
• Copper(II) Triflate-Catalyzed Aerobic Oxidative CH Functionalization of Glycine Derivatives with Olefins and Organoboranes
  作者：Zhiyu Xie、Jiong Jia、Xigong Liu、Lei Liu

  DOI：10.1002/adsc.201501015

  日期：2016.3.17

  triflate‐catalyzed aerobic oxidative CH functionalization of glycine derivatives with olefins and organoboranes has been established. The mild reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both glycine derivatives and the two types of nucleophilic components, allowing for the facile synthesis of diverse substituted quinolines and glycine derivatives bearing

  建立了经济实用的三氟甲磺酸铜（II）催化甘氨酸衍生物与烯烃和有机硼烷的好氧氧化CH功能化。温和的反应具有优异的官能团耐受性，并且在甘氨酸衍生物和两种类型的亲核组分方面均显示出广阔的范围，从而可以轻松合成各种取代的喹啉和甘氨酸衍生物，这些衍生物在α-中具有各种功能模式位置。