dimethyl 4-benzoylquinoline-2,3-dicarboxylate | 1373169-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 4-benzoylquinoline-2,3-dicarboxylate
• 英文别名: Dimethyl 4-benzoylquinoline-2,3-dicarboxylate
• CAS: 1373169-75-5
• 化学式: C₂₀H₁₅NO₅
• 分子量: 349.343
• InChiKey: REGYRTKRDXVUQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl 2-(2-(phenylethynyl)phenylamino)fumarate 在 1,10-菲罗啉 、 copper(I) bromide dimethylsulfide complex 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 以81%的产率得到dimethyl 4-benzoylquinoline-2,3-dicarboxylate
  参考文献：
  名称：

  Copper-Catalyzed Aerobic Intramolecular Carbo- and Amino-Oxygenation of Alkynes for Synthesis of Azaheterocycles

  摘要：

  A synthetic method of highly substituted quinolines has been developed from N-(2-alkynylaryl)enamine carboxylates under Cu-catalyzed aerobic conditions via intramolecular carbo-oxygenation of alkynes. This strategy was further applied for N-alkynylamidines for amino-oxygenation of alkynes, leading to imidazole and quinazoline derivatives.

  DOI：

  10.1021/ol3007106

文献信息

• Metal‐Free Oxidative Annulation/Cyclization of 1,6‐Enynes for the Synthesis of 4‐Carbonylquinolines
  作者：Xiao‐Feng Xia、Wei He、Dawei Wang

  DOI：10.1002/adsc.201900013

  日期：2019.6.18

  Herein we report on the development of a metal‐free oxidative annulation reaction of 1,6‐enynes, leading to 4‐carbonylquinolines by using dioxygen as a green sustainable oxidant. Key advances include the use of readily available tert‐butyl nitrite (TBN) to promote radical annulation of 1,6‐enynes and easy‐to‐handle reaction conditions. Preliminary mechanistic studies including radical capture reactions

  本文中，我们报告了通过使用双氧作为绿色可持续氧化剂，开发无金属的1,6-炔烃氧化环化反应，从而生成4-羰基喹啉的方法。关键的进展包括使用现成的亚硝酸叔丁酯（TBN）来促进1,6-炔烃的自由基环化和易于处理的反应条件。还进行了包括自由基捕获反应和同位素标记实验在内的初步机理研究。
• Copper-Catalyzed Aerobic Oxidative Carbocyclization Reactions of N-[(E)-Stilben-2-yl]amine Derivatives
  作者：Che-Ping Chuang、Cheng-Yen Lu

  DOI：10.1055/s-0034-1378870

  日期：——

  aerobic oxidative carbocyclization reactions of α-substituted N-[(E)-stilben-2-yl]acetamides, via the intramolecular carbocupration onto the alkenyl moiety, produced 3-substituted 2-quinolinones. Several useful functional groups including benzoyl, acetyl, cyano, and ethoxycarbonyl groups are compatible with the reaction conditions. This strategy was further applied to N-[(E)-stilben-2-yl]enamines to prepare

  摘要 已经开发出一种高度官能化的2-喹啉酮和喹啉的合成方法。α-取代的N -[（E）-stilben-2-yl]乙酰胺的铜（II）催化的需氧氧化碳环化反应，通过分子内碳键合到烯基上，产生3-取代的2-喹啉酮。几种有用的官能团包括苯甲酰基，乙酰基，氰基和乙氧基羰基与反应条件相容。将该策略进一步应用于N -[（E）-stilben-2-yl]烯胺，以高收率制备2，3-二取代的喹啉。 已经开发出一种高度官能化的2-喹啉酮和喹啉的合成方法。α-取代的N -[（E）-stilben-2-yl]乙酰胺的铜（II）催化的需氧氧化碳环化反应，通过分子内碳键合到烯基上，产生3-取代的2-喹啉酮。几种有用的官能团包括苯甲酰基，乙酰基，氰基和乙氧基羰基与反应条件相容。将该策略进一步应用于N -[（E）-stilben-2-yl]烯胺，以高收率制备2，3-二取代的喹啉。
• Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives
  作者：Xiao-Feng Xia、Guo-Wei Zhang、Dawei Wang、Su-Li Zhu

  DOI：10.1021/acs.joc.7b01206

  日期：2017.8.18

  synthesis of quinoline derivatives by using dioxygen as an oxygen source is developed. By using visible light, the direct oxidative cyclization of aromatic enamines with alkynes or alkenes can be achieved at mild conditions with an aid of copper or palladium catalysts, and a variety of multisubstituted quinoline derivatives could be obtained in good to moderate yields under mild reaction conditions.

  开发了以双氧为氧源合成喹啉衍生物的双过渡金属可见光光氧化还原催化剂。通过使用可见光，借助铜或钯催化剂，可以在温和的条件下实现芳香族烯胺与炔烃或烯烃的直接氧化环化反应，在温和的反应条件下，可以以中等至中等的收率获得各种多取代的喹啉衍生物。 。
• Copper-Catalyzed Oxidative Cyclization of Enynes for the Synthesis of 4-Carbonyl-quinolines with O₂
  作者：Xiao-Feng Xia、Lu-Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/ol300896h

  日期：2012.5.18

  A novel copper-catalyzed oxidative cyclization of enynes and in situ formed enynes leading to 4-carbonyl-quinolines by using dioxygen as an oxygen source has been developed.

  通过使用双氧作为氧源，开发了一种新型的铜催化的炔烃和原位形成的炔烃的氧化铜环化反应，生成4-羰基喹啉。
• Copper-Catalyzed Aerobic Intramolecular Carbo- and Amino-Oxygenation of Alkynes for Synthesis of Azaheterocycles
  作者：Kah Kah Toh、Stephen Sanjaya、Sophian Sahnoun、Sin Yee Chong、Shunsuke Chiba

  DOI：10.1021/ol3007106

  日期：2012.5.4

  A synthetic method of highly substituted quinolines has been developed from N-(2-alkynylaryl)enamine carboxylates under Cu-catalyzed aerobic conditions via intramolecular carbo-oxygenation of alkynes. This strategy was further applied for N-alkynylamidines for amino-oxygenation of alkynes, leading to imidazole and quinazoline derivatives.