5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline | 82082-03-9

• 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: 5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline
• 英文别名: 2,4-Dimethyl-5,6-dimethoxy-8-nitroquinoline
• CAS: 82082-03-9
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: BHRWANJAKOXBCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以86%的产率得到8-amino-5,6-dimethoxy-2,4-dimethylquinoline
  参考文献：
  名称：

  Antimalarials. 13. 5-Alkoxy analogs of 4-methylprimaquine

  摘要：

  A series of nuclear and side-chain analogues of 4-methylprimaquine incorporating an alkoxy group in the 5-position of the quinoline nucleus has been prepared. The compounds were tested for suppressive antimalarial activity against Plasmodium berghei in mice and for radical curative antimalarial activity against Plasmodium cynomolgi in the rhesus monkey. Although the toxicity problems characteristic of the 8-aminoquinolines were not overcome, several of the compounds, surprisingly, were highly effective as both blood and tissue schizonticidal agents.

  DOI：

  10.1021/jm00350a016
• 作为产物：
  描述：

  3-戊烯-2-酮 、 2-硝基-4，5-二甲氧基苯胺 在 silica gel 、 异丙醇 作用下， 以 ethyl acetate benzene 为溶剂， 以to afford 14% yield of golden 5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline的产率得到5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline
  参考文献：
  名称：

  Process for production of 8-NHR quinolines

  摘要：

  公开了一种从8-氨基喹啉生产8-NHR喹啉的改进工艺。该工艺包括在80°C至90°C沸点的胺的存在下，将8-氨基喹啉与取代烷基卤代物反应。该胺作为酸受体，因此形成的胺盐可以在不需要昂贵或耗时的纯化步骤的情况下高效分离出形成的8-NHR喹啉。该反应可以在溶剂的存在下进行，例如醇类。

  公开号：

  US04167638A1

文献信息

• Process for production of 8-NHR quinolines
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04167638A1

  公开（公告）日：1979-09-11

  An improved process for producing 8-NHR quinolines from 8-aminoquinolines disclosed. The process comprises reacting 8-aminoquinolines with a substituted alkyl halide in the presence of an amine having a boiling point of 80.degree.-90.degree. C. The amine functions as an acid acceptor whereby the amine salt formed may be efficiently separated from the 8-NHR quinoline formed without expensive or time consuming purification steps. The reaction may be carried out in the presence of a solvent such as an alcohol.

  一种改进的方法用于从8-氨基喹啉制备8-NHR喹啉。该方法包括在存在沸点为80度至90度的胺的情况下，将8-氨基喹啉与取代烷基卤化物反应。胺起到酸受体的作用，从而形成的胺盐可以在无需昂贵或耗时的纯化步骤的情况下有效地与形成的8-NHR喹啉分离。反应可以在存在溶剂（如醇类）的情况下进行。
• LAMONTAGNE, M. P.;MARKOVAC, A.;KHAN, M. S., J. MED. CHEM., 1982, 25, N 3, 964-968
  作者：LAMONTAGNE, M. P.、MARKOVAC, A.、KHAN, M. S.

  DOI：——

  日期：——
• US4167638A
  申请人：——

  公开号：US4167638A

  公开（公告）日：1979-09-11
• Antimalarials. 13. 5-Alkoxy analogs of 4-methylprimaquine
  作者：Maurice P. LaMontagne、Anica Markovac、M. Sami Khan

  DOI：10.1021/jm00350a016

  日期：1982.8

  A series of nuclear and side-chain analogues of 4-methylprimaquine incorporating an alkoxy group in the 5-position of the quinoline nucleus has been prepared. The compounds were tested for suppressive antimalarial activity against Plasmodium berghei in mice and for radical curative antimalarial activity against Plasmodium cynomolgi in the rhesus monkey. Although the toxicity problems characteristic of the 8-aminoquinolines were not overcome, several of the compounds, surprisingly, were highly effective as both blood and tissue schizonticidal agents.