6,7-dimethoxy-3-methoxycarbonyl-4-hydroxyquinolin-2(1H)-one | 243841-56-7

• 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: 6,7-dimethoxy-3-methoxycarbonyl-4-hydroxyquinolin-2(1H)-one
• 英文别名: methyl 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate；methyl 4-hydroxy-6,7-dimethoxy-2-oxo-1H-quinoline-3-carboxylate
• CAS: 243841-56-7
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: KUCXOONYMRJPCE-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  497.9±45.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-3-methoxycarbonyl-4-hydroxyquinolin-2(1H)-one 在 溴 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 2,3-dibromopropylamide
  参考文献：
  名称：

  4-hydroxy-2-quinolones. 202*. Synthesis, chemical and biological properties of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides

  摘要：

  In continuation of the search for potential analgesics amongst 4-hydroxyquinol-2-one derivatives we have proposed and carried out a preparative method of synthesis of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid alkylamides. It has been shown that bromination of 4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid allylamide using an equivalent of molecular bromine occurs with a conventional addition of the halogen to the allyl double bond and not with halocyclization. The results of the study of the analgesic properties of the compounds prepared are presented.

  DOI：

  10.1007/s10593-012-0992-4
• 作为产物：
  描述：

  dimethyl 2-(4,5-dimethoxy-2-ethoxycarbonylaminobenzoyl)malonate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到6,7-dimethoxy-3-methoxycarbonyl-4-hydroxyquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 3-Substituted 4-Hydroxyquinolin-2-ones via C-Acylation Reactions of Active Methylene Compounds with Functionalized 3,1-Benzoxazin-4-ones

  摘要：

  DOI：

  10.3987/com-99-8508

文献信息

• Design, synthesis and In vitro evaluation of potent, novel, small molecule inhibitors of plasminogen activator inhibitor-1
  作者：Adrian Folkes、S.David Brown、Lynne E. Canne、Jocelyn Chan、Erin Engelhardt、Sergey Epshteyn、Richard Faint、Julian Golec、Art Hanel、Patrick Kearney、James W. Leahy、Morrison Mac、David Matthews、Michael P. Prisbylla、Jason Sanderson、Reyna J. Simon、Zerom Tesfai、Nigel Vicker、Shouming Wang、Robert R. Webb、Peter Charlton

  DOI：10.1016/s0960-894x(02)00078-1

  日期：2002.4

  We have synthesized and evaluated a series of tetramic acid-based and hydroxvquinolinone-based inhibitors of plasminogen activator inhibitor-1 (PAI-1). These studies resulted in the identification of several compounds which showed excellent potency against PAI-1. The design, synthesis and SAR of these compounds are described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Brown, Australian Journal of Chemistry, 1955, vol. 8, p. 121,123
  作者：Brown

  DOI：——

  日期：——
• Anet et al., Australian Journal of Scientific Research, Series A: Physical Sciences, 1952, vol. <A> 5, p. 412,416
  作者：Anet et al.

  DOI：——

  日期：——
• US4119720A
  申请人：——

  公开号：US4119720A

  公开（公告）日：1978-10-10
• US4190659A
  申请人：——

  公开号：US4190659A

  公开（公告）日：1980-02-26

表征谱图