1-乙基-4-氯-2-氧代-1,2-二氢喹啉-3-羧酸乙酯 | 169216-65-3

• 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
• 中文名称: 1-乙基-4-氯-2-氧代-1,2-二氢喹啉-3-羧酸乙酯
• 英文名称: ethyl 4-chloro-1-ethyl-2-oxo-1,2-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 4-chloro-1-ethyl-2-oxoquinoline-3-carboxylate
• CAS: 169216-65-3
• 化学式: C₁₄H₁₄ClNO₃
• 分子量: 279.723
• InChiKey: XVDDORJDEBUBPV-UHFFFAOYSA-N

物化性质

• 沸点：
  372.7±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙基-4-氯-2-氧代-1,2-二氢喹啉-3-羧酸乙酯 在 sodium acetate 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 100.0h， 以76%的产率得到1-乙基-1,2-二氢-4-羟基-2-氧代-3-喹啉羧酸乙酯
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 30 Alkylation of 1H-2-oxo-3-carbethoxy-4-hydroxyquinoline

  摘要：

  DOI：

  10.1007/bf01176973
• 作为产物：
  描述：

  1-乙基-1,2-二氢-4-羟基-2-氧代-3-喹啉羧酸乙酯 在 三氯氧磷 作用下， 反应 0.08h， 生成 1-乙基-4-氯-2-氧代-1,2-二氢喹啉-3-羧酸乙酯
  参考文献：
  名称：

  4-羟基-2-喹诺酮类。167 *。1-烷基取代的4-羟基-2-氧-2-氧-1,2-二氢喹啉-3-羧酸乙酯与三氯氧磷反应的研究

  摘要：

  用回流的三氯氧化磷长时间处理乙基1-烷基-4-羟基-2-羟基-2-氧代-1,2-二氢喹啉-3-羧酸乙酯不仅得到目标4-氯衍生物，而且还伴随着1-的明显损失。 N-烷基形成副产物2，4-二氯-3-乙氧基羰基喹啉。

  DOI：

  10.1007/s10593-009-0367-7

文献信息

• 4-Hydroxy-2-quinolones 141. Synthesis and structure of 5R-3-hydroxy-1,5-dihydropyrazolo[4,3-c]quinolin-4-ones
  作者：I. V. Ukrainets、V. V. Kravtsova、A. A. Tkach、G. Sim

  DOI：10.1007/s10593-008-0032-6

  日期：2008.2

  Treatment of 1R-4-chloro-3-ethoxycarbonyl-2-oxo-1,2-dihydroquinolines with p-toluenesulfonylhydrazide in refluxing ethanol and in the presence of triethylamine gives the 3-hydroxy-5R-1,5-dihydropyrazolo[4,3-c]quinolin-4-ones. The possible mechanism of formation, features of the steric structure of the synthesized compounds, and their NMR and mass spectra are discussed.
• 4-hydroxy-2-quinolones. 114. Synthesis and structure of 6-R-5-hydroxy-2,4-dioxo-2,3,4,6-tetrahydrobenzo-[c][2,7]naphthyridine-1-carbonitriles
  作者：I. V. Ukrainets、N. L. Bereznyakova、V. A. Parshikov、S. V. Shishkina

  DOI：10.1007/s10593-007-0095-9

  日期：2007.5
• A novel templates of piperazinyl-1,2-dihydroquinoline-3-carboxylates: Synthesis, anti-microbial evaluation and molecular docking studies
  作者：Saleha Banu、Rajitha Bollu、Mohammad Naseema、P. Mary Gomedhika、Lingaiah Nagarapu、K. Sirisha、C. Ganesh Kumar、Shravan Kumar Gundasw

  DOI：10.1016/j.bmcl.2018.03.007

  日期：2018.4

  A series of piperazinyl-1,2-dihydroquinoline carboxylates were synthesized by the reaction of ethyl 4-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylates with various piperazines and their structures were confirmed by H-1 NMR, C-13 NMR, IR and mass spectral analysis. All the synthesized compounds were screened for their in vitro antimicrobial activities. Further, the in silico molecular docking studies of the active compounds was performed to explore the binding interactions between piperazinyl-1,2-dihydroquinoline carboxylate derivatives and the active site of the Staphylococcus aureus (CrtM) dehydrosqualene synthase (PDB ID: 2ZCQ). The docking studies revealed that the synthesized derivatives showed high binding energies and strong H-bond interactions with the dehydrosqualene synthase validating the observed antimicrobial activity data. Based on antimicrobial activity and docking studies, the compounds 9b and 10c were identified as promising antimicrobial lead molecules. This study might provide insights to identify new drug candidates that target the S. aureus virulence factor, dehydrosqualene synthase. (C) 2018 Elsevier Ltd. All rights reserved.
• 4-Hydroxy-2-quinolones 137. Synthesis, structure, and spectroscopic characteristics of diethyl 2,2′-dioxo-1,2,3,4,1′,2′,3′,4′-octahydro[4,4′]biquinolinyl-3,3′-dicarboxylate
  作者：I. V. Ukrainets、A. A. Tkach、V. V. Kravtsova、A. V. Turov

  DOI：10.1007/s10593-007-0236-1

  日期：2007.12
• 4-Hydroxy-2-quinolones. 84. Synthesis of 5-R-5H-5,7a,12-Triazabenzo[a]anthracene-6,7-diones
  作者：I. V. Ukrainets、L. V. Sidorenko、O. V. Gorokhova

  DOI：10.1007/s10593-005-0245-x

  日期：2005.7