ethyl 2-cyclopropyl-6,7-difluoro-4-(4-fluorophenylthio)quinoline-3-carboxylate | 1202384-01-7

• 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: ethyl 2-cyclopropyl-6,7-difluoro-4-(4-fluorophenylthio)quinoline-3-carboxylate
• 英文别名: Ethyl 2-cyclopropyl-6,7-difluoro-4-(4-fluorophenyl)sulfanylquinoline-3-carboxylate
• CAS: 1202384-01-7
• 化学式: C₂₁H₁₆F₃NO₂S
• 分子量: 403.425
• InChiKey: VWOQVQOSDYCCCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyclopropyl-6,7-difluoro-4-(4-fluorophenylthio)quinoline-3-carboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以98%的产率得到C₁₉H₁₄F₃NOS
  参考文献：
  名称：

  Synthesis and HMG-CoA reductase inhibition of 2-cyclopropyl-4-thiophenyl-quinoline mevalonolactones

  摘要：

  A novel series of 2-cyclopropyl-4-thiophenyl quinoline-based mevalonolactones were synthesized from the substituted anilines by several reactions. Among them, (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4-(4-fluoro-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1d), (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4-(3-methoxy-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetra-hydro-4-hydroxy-2H-pyran-2-one (1f) and (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4,7-di(3-methoxy-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1q) showed potent HMG-CoA reductase inhibitory activity comparable with pitavastatin. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.021
• 作为产物：
  描述：

  3,4-二氟苯胺 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 ethyl 2-cyclopropyl-6,7-difluoro-4-(4-fluorophenylthio)quinoline-3-carboxylate
  参考文献：
  名称：

  Poly-halo-quinoline-3-carboxylates 与苯酚、硫代苯酚或 N-甲基苯胺的区域选择性 SNAr 反应

  摘要：

  通过SNAr反应，聚卤-喹啉-3-羧酸酯如4-氯-2-环丙基-6,7-二氟-喹啉-3-羧酸乙酯和4-氯-2-环丙基-5,6-二氟乙酯-quinoline-3-carboxylates 被转化为 4-phenoxy 或 4-phenylthio 或 4-(N-methyl)phenylamino-6,7 (or 5,6)-difluoro-quinoline-3-carboxylates 或 4,7-二取代、4,5-二取代、4,6,7-三取代和4,5,6-三取代产物在温和条件下以中等至极好的产率获得。观察到高度区域选择性的单或多取代。

  DOI：

  10.1080/00397910903531656

文献信息

• Synthesis and HMG-CoA reductase inhibition of 2-cyclopropyl-4-thiophenyl-quinoline mevalonolactones
  作者：Shikui Zhao、Weicheng Zhou、Jun liu

  DOI：10.1016/j.bmc.2009.10.021

  日期：2009.12

  A novel series of 2-cyclopropyl-4-thiophenyl quinoline-based mevalonolactones were synthesized from the substituted anilines by several reactions. Among them, (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4-(4-fluoro-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1d), (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4-(3-methoxy-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetra-hydro-4-hydroxy-2H-pyran-2-one (1f) and (4R,6S)-6-[(E)-2-(2-cyclopropyl-6-fluoro-4,7-di(3-methoxy-thiophenyl)-quinoline-3-yl)-ethenyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (1q) showed potent HMG-CoA reductase inhibitory activity comparable with pitavastatin. (c) 2009 Elsevier Ltd. All rights reserved.
• A Regioselective S_NAr Reaction of Poly-halo-quinoline-3-carboxylates with Phenol, Thiophenol, or <i>N</i>-Methylaniline
  作者：Shikui Zhao、Weicheng Zhou

  DOI：10.1080/00397910903531656

  日期：2010.12.21

  By SNAr reaction, poly-halo-quinoline-3-carboxylates such as ethyl 4-chloro-2-cyclopropyl-6,7-difluoro-quinoline-3-carboxylate and ethyl 4-chloro-2-cyclopropyl-5,6-difluoro-quinoline-3-carboxylate were transformed into the 4-phenoxy or 4-phenylthio or 4-(N-methyl)phenylamino-6,7 (or 5,6)-difluoro-quinoline-3-carboxylates or the 4,7-disubstituted, 4,5-disubstituted, 4,6,7-trisubstituted and 4,5,6-trisubstituted

  通过SNAr反应，聚卤-喹啉-3-羧酸酯如4-氯-2-环丙基-6,7-二氟-喹啉-3-羧酸乙酯和4-氯-2-环丙基-5,6-二氟乙酯-quinoline-3-carboxylates 被转化为 4-phenoxy 或 4-phenylthio 或 4-(N-methyl)phenylamino-6,7 (or 5,6)-difluoro-quinoline-3-carboxylates 或 4,7-二取代、4,5-二取代、4,6,7-三取代和4,5,6-三取代产物在温和条件下以中等至极好的产率获得。观察到高度区域选择性的单或多取代。