ethyl 1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate | 60442-66-2

• 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 1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate
• 英文别名: Ethyl-N-methyl-4-oxochinolin-2-carboxylat；1-methyl-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid ethyl ester；ethyl 1,4-dihydro-1-methyl-4-oxo-quinoline-2-carboxylate；ethyl 1-methyl-4-oxoquinoline-2-carboxylate
• CAS: 60442-66-2
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: ANYMJGVZWGJGSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl 2-(methyl(phenyl)amino)maleate 在 polyphosphoric acid 作用下， 以 neat (no solvent) 为溶剂， 生成 ethyl 1-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate
  参考文献：
  名称：

  Facile synthesis of 4-quinolone derivatives via one-pot cascade reaction under transition-metal-free conditions

  摘要：

  A practical and efficient strategy has been described for the preparation of 4-quinolone derivatives. Using commercially available diethyl acetylenedicarboxylate and aromatic amines as starting materials, the synthetic protocol has been achieved and afforded the product via hydroamination at room temperature followed by PPA-catalyzed intramolecular ring closure. The products can be easily obtained in high yields. Conditions and mechanism of the reaction have also been investigated. This protocol is environmentally friendly and transition-metal-free, with advantages including short reaction time, convenient operation, and mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.04.060

文献信息

• Alkylation of 2- and 3-alkoxycarbonyl-4-quinolinones. DFT study on the regioselectivity
  作者：María S. Shmidt、Pau Arroyo Mañez、Carlos A. Stortz、Isabel A. Perillo、Daniel Vega、María M. Blanco

  DOI：10.1016/j.molstruc.2016.08.057

  日期：2017.1

  O-alkylated products. The behavior in basic medium of compounds 1 differs from the 3-alkoxycarbonyl-4-quinolinones (4) isomers suggesting that the position of the carboxylate group determines the regioselectivity of the reaction. DFT calculations allow us to conclude that for 3-alkoxycarbonyl-4-quinolinones, the N-alkylation would be thermodynamically and kinetically favored. But for 2-alkoxycarbonyl-4-quinolinones

  摘要 2-烷氧基羰基-4-喹啉酮(1) 与多种烷基化试剂在不同条件下反应，生成相应的O-烷基化产物。化合物 1 在碱性介质中的行为不同于 3-alkoxycarbonyl-4-quinolinones (4) 异构体，表明羧酸根的位置决定了反应的区域选择性。DFT 计算使我们得出结论，对于 3-烷氧基羰基-4-喹啉酮，N-烷基化在热力学和动力学上都是有利的。但是对于 2-烷氧基羰基-4-喹啉酮，环的 2-位侧链阻止了与连续杂原子的平面近似，从而导致更有利的 O-烷基化过渡态。O-烷基化产物的晶体结构由单晶 X 射线衍射测定。
• Process for preparing certain pyrano[3,2-g]quinoline 2,8-dicarboxylates
  申请人：Fisons Limited

  公开号：US04328341A1

  公开（公告）日：1982-05-04

  There is described a process for the production of a 1,4-dihydro-4-oxo-quinoline-2-carboxylic acid, or a salt, ester or amide thereof, which comprises cyclization of a corresponding 2-aminobenzoyl pyruvic acid or an ester thereof, and if desired or necessary converting the resulting product to an appropriate salt, ester or amide thereof, or vice versa.

  描述了一种生产1,4-二氢-4-氧基-喹啉-2-羧酸或其盐、酯或酰胺的过程，包括将相应的2-氨基苯甲酰丙酸或其酯环化，并在必要时将所得产物转化为相应的盐、酯或酰胺，或者反之亦然。
• Certain diacetyl-amino-phenolic derivatives
  申请人：Fisons Limited

  公开号：US04414416A1

  公开（公告）日：1983-11-08

  There is described a process for the production of a 1,4-dihydro-4-oxo-quinoline-2-carboxylic acid, or a salt, ester or amide thereof, which comprises cyclization of a corresponding 2-aminobenzoyl pyruvic acid or an ester thereof, and if desired or necessary converting the resulting product to an appropriate salt, ester or amide thereof, or vice versa.

  描述了一种生产1,4-二氢-4-氧基-喹啉-2-羧酸或其盐、酯或酰胺的方法，该方法包括将相应的2-氨基苯甲酰丙酸或其酯环化，如果需要或必要，将所得产物转化为适当的盐、酯或酰胺，或者反之亦然。
• A process for the production of 1,4-dihydro-4-oxo-quinoline-2-carboxylic acids, or salts, esters or amides thereof and intermediates therefor
  申请人：FISONS plc

  公开号：EP0030423A1

  公开（公告）日：1981-06-17

  There is described a process for the production of a 1,4-dihydro-4-oxo-quinoline-2-carboxylic acid. or a salt, ester or amide thereof, which comprises cyclisation of a corresponding 2-aminobenzoyl pyruvic acid or an ester thereof, and if desired or necessary converting the resulting product to an appropriate salt, ester or amide thereof, or vice versa.

  本发明描述了一种 1,4-二氢-4-氧代喹啉-2-羧酸或其盐、酯或酰胺的生产工艺，该工艺包括相应的 2-氨基苯甲酰基丙酮酸或其酯的环化，如果需要或必要，将所得产物转化为其适当的盐、酯或酰胺，反之亦然。
• A New Efficient Route to 4-Oxo-1,4-dihydroquinoline-2-carboxylic Esters
  作者：Stephen C. W. Coltman、Stephen C. Eyley、Richard A. Raphael

  DOI：10.1055/s-1984-30762

  日期：——