5-fluoro-6-methoxy-8-nitroquinoline | 316-77-8

• 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-nitroquinoline
• 英文别名: 5-fluoro-6-methoxy-8-nitro-quinoline；5-Fluor-6-methoxy-8-nitro-chinolin
• CAS: 316-77-8
• 化学式: C₁₀H₇FN₂O₃
• 分子量: 222.176
• InChiKey: RXLHRBYKVVIMBW-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  385.7±37.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 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：
  67.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-fluoro-6-methoxy-8-nitroquinoline 在 palladium on activated charcoal sodium hypophosphite 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 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
• 作为产物：
  描述：

  2-氟苯甲醚 在 arsenic(V) oxide 、 硫酸 、 水 、 硝酸 、 乙酸酐 、 溶剂黄146 、 铂 作用下， 生成 5-fluoro-6-methoxy-8-nitroquinoline
  参考文献：
  名称：

  Elderfield et al., Journal of the American Chemical Society, 1946, vol. 68, p. 1583

  摘要：

  DOI：

文献信息

• Selective direct fluorination of quinoline derivatives
  作者：Richard D Chambers、Darren Holling、Graham Sandford、Horst Puschmann、Judith A.K Howard

  DOI：10.1016/s0022-1139(02)00156-2

  日期：2002.10

  Direct fluorination of various quinoline derivatives in acidic reaction media gives fluorinated quinoline products arising from selective, efficient electrophilic substitution processes. (C) 2002 Elsevier Science B.V. All rights reserved.
• Elemental fluorine
  作者：Richard D. Chambers、Darren Holling、Graham Sandford、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/j.jfluchem.2003.11.012

  日期：2004.5

  Direct fluorination of various quinoline derivatives in acidic reaction media gives fluorinated quinoline products arising from electrophilic substitution processes. (C) 2003 Elsevier B.V. All rights reserved.
• Elderfield et al., Journal of the American Chemical Society, 1946, vol. 68, p. 1583
  作者：Elderfield et al.

  DOI：——

  日期：——
• 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.