ethyl 4-(4-(tert-butyl)phenyl)-6-methoxyquinoline-2-carboxylate | 1174133-22-2

• 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-(tert-butyl)phenyl)-6-methoxyquinoline-2-carboxylate
• 英文别名: Ethyl 4-(4-tert-butylphenyl)-6-methoxyquinoline-2-carboxylate
• CAS: 1174133-22-2
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: IWBHGKOAIGXIDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-(tert-butyl)phenyl)-6-methoxyquinoline-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以81%的产率得到9-(4-(tert-butyl)phenyl)-7-methoxyfuro[3,4-b]quinolin-3(1H)-one
  参考文献：
  名称：

  水性介质中高取代度喹啉的一锅法合成及其在阿兹木聚糖合成中的应用

  摘要：

  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。

  DOI：

  10.1002/ejoc.202000906
• 作为产物：
  描述：

  4-叔-丁基苯基乙炔 、 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92%的产率得到ethyl 4-(4-(tert-butyl)phenyl)-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

• 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。
• 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.