3-chloro-6,7-dimethoxy-4-methylquinolin-2(1H)-one | 1234198-77-6

• 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: 3-chloro-6,7-dimethoxy-4-methylquinolin-2(1H)-one
• 英文别名: 3-chloro-6,7-dimethoxy-4-methyl-2-quinolone；3-chloro-6,7-dimethoxy-4-methyl-1H-quinolin-2-one
• CAS: 1234198-77-6
• 化学式: C₁₂H₁₂ClNO₃
• 分子量: 253.685
• InChiKey: PNPZSLXXAFKTMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,7-dimethoxy-4-methyl-quinolin-2-ol 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以78%的产率得到3-chloro-6,7-dimethoxy-4-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclization of Anilides with Substituted Propiolates or Acrylates: An Efficient Route to 2-Quinolinones

  摘要：

  A Ru-catalyzed cyclization of anilides with propiolates or acrylates affording 2-quinolinones having diverse functional groups in good to excellent yields is described. Later, 2-quinolinones were converted into 3-halo-2-quinolinones and 2-chloroquinolines. The proposed mechanism was strongly supported by experimental evidence and deuterium labeling studies.

  DOI：

  10.1021/ol501548e

文献信息

• A new general approach to 4-substituted-3-halo-2-quinolones
  作者：Shuai Zhao、Yan-hong He、Di Wu、Zhi Guan

  DOI：10.1016/j.jfluchem.2010.01.008

  日期：2010.5

  A general procedure for the preparation of 4-substituted-3-halo-2-quinolones (halo = F, Cl, Br) utilizing 2-halo diethylphosphonoacetic acids (halo = F, Cl, Br) and o-aminophenylketones as the starting materials is described. The title compounds are obtained by an intramolecular Homer-Wadsworth-Emmons olefination of halogen-containing N-acyl-o-aminophenylketones. The transformation process is generally applicable under mild conditions. (C) 2010 Elsevier B.V All rights reserved.