5-fluoro-6-methoxy-8-aminoquinoline | 170809-21-9

• 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-fluoro-6-methoxy-8-aminoquinoline
• 英文别名: 5-Fluoro-6-methoxyquinolin-8-amine
• CAS: 170809-21-9
• 化学式: C₁₀H₉FN₂O
• 分子量: 192.193
• InChiKey: SMYAUCJUOSDUHX-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±37.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-fluoro-6-methoxy-8-aminoquinoline 在 一水合肼 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 4-N-(5-fluoro-6-methoxyquinolin-8-yl)pentane-1,4-diamine
  参考文献：
  名称：

  Synthesis of the 8-aminoquinoline antimalarial 5-fluoroprimaquine

  摘要：

  Several approaches to the synthesis of 5-fluoro-6-methoxy-8-nitroquinoline 5, the key intermediate required for the synthesis of 9-fluoroprimaquine, were investigated. In one approach, 5-chloro-6-methoxy-8-nitroquinoline was synthesised and treated with a variety of nucleophilic sources of fluoride. In another approach, electrophilic substitution of 6-methoxy-8-nitroquinoline with (N-fluorosulfonimide, NFS1) was investigated. The final approach to 5 involved a modified Skraup reaction of 5-fluoro-4-methoxy-2-nitroaniline which gave the required intermediate in 30% yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00177-x
• 作为产物：
  描述：

  6-甲氧基-8-硝基喹啉 在 palladium on activated charcoal sodium hypophosphite 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 5-fluoro-6-methoxy-8-aminoquinoline
  参考文献：
  名称：

  Synthesis of the 8-aminoquinoline antimalarial 5-fluoroprimaquine

  摘要：

  Several approaches to the synthesis of 5-fluoro-6-methoxy-8-nitroquinoline 5, the key intermediate required for the synthesis of 9-fluoroprimaquine, were investigated. In one approach, 5-chloro-6-methoxy-8-nitroquinoline was synthesised and treated with a variety of nucleophilic sources of fluoride. In another approach, electrophilic substitution of 6-methoxy-8-nitroquinoline with (N-fluorosulfonimide, NFS1) was investigated. The final approach to 5 involved a modified Skraup reaction of 5-fluoro-4-methoxy-2-nitroaniline which gave the required intermediate in 30% yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00177-x