2-[4-(5-Fluoro-6-methoxy-quinolin-8-ylamino)-pentyl]-isoindole-1,3-dione | 206658-68-6

• 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: 2-[4-(5-Fluoro-6-methoxy-quinolin-8-ylamino)-pentyl]-isoindole-1,3-dione
• CAS: 206658-68-6
• 化学式: C₂₃H₂₂FN₃O₃
• 分子量: 407.444
• InChiKey: RAEZQWOFBHOEKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[4-(5-Fluoro-6-methoxy-quinolin-8-ylamino)-pentyl]-isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以60%的产率得到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 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 2-[4-(5-Fluoro-6-methoxy-quinolin-8-ylamino)-pentyl]-isoindole-1,3-dione
  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

文献信息

• Synthesis of the 8-aminoquinoline antimalarial 5-fluoroprimaquine
  作者：Paul M. O'Neill、Richard C. Storr、B. Kevin Park

  DOI：10.1016/s0040-4020(98)00177-x

  日期：1998.4

  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.