(3aSR,4SR,9bSR)-8-fluoro-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline | 1062584-14-8

• 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: (3aSR,4SR,9bSR)-8-fluoro-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 英文别名: 8-Fluoro-4-(2-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline；(3aS,4S,9bS)-8-fluoro-4-(furan-2-yl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• CAS: 1062584-14-8
• 化学式: C₁₅H₁₄FNO₂
• 分子量: 259.28
• InChiKey: BGXDUIOHIMCBER-LKTVYLICSA-N

物化性质

• 熔点：
  101-102 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  379.4±42.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aSR,4SR,9bSR)-8-fluoro-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline 在 sulfur 作用下， 反应 4.0h， 以30%的产率得到2'-[6-fluoro-2-(2-furyl)-3-quinolinyl]-1'-ethanol
  参考文献：
  名称：

  Synthesis and oxidation of 2-furyl-4-R-substituted and furo[3,2-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines and quinolines*

  摘要：

  2-Furyl-4-substituted and furo[2,3-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines were obtained for the first time from 8-aminoquinolines using the Povarov reaction. Various oxidizing agents were shown to effect the elimination of the substituent at C(4) with subsequent aromatization of the tetrahydroquinoline fragment.

  DOI：

  10.1007/s10593-009-0271-1
• 作为产物：
  描述：

  糠醛 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 生成 (3aSR,4SR,9bSR)-8-fluoro-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis and oxidation of 2-furyl-4-R-substituted and furo[3,2-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines and quinolines*

  摘要：

  2-Furyl-4-substituted and furo[2,3-c]-condensed 1,2,3,4-tetrahydro-1,10-phenanthrolines were obtained for the first time from 8-aminoquinolines using the Povarov reaction. Various oxidizing agents were shown to effect the elimination of the substituent at C(4) with subsequent aromatization of the tetrahydroquinoline fragment.

  DOI：

  10.1007/s10593-009-0271-1

文献信息

• New synthetic approach to epoxyisoindolo[2,1-a]quinolines based on cycloaddition reactions of 2-furyl-substituted tetrahydroquinolines with maleic anhydride and acryloyl chloride
  作者：F. I. Zubkov、V. P. Zaitsev、A. S. Peregudov、N. M. Mikhailova、A. V. Varlamov

  DOI：10.1007/s11172-007-0159-0

  日期：2007.5

  A procedure was developed for the synthesis of hydrogenated furyl-substituted furo[3,2-c]quinolines, pyrano[3,2-c]quinolines, and 4-ethoxy-and 4-(2-oxopyrrolidin-1-yl)quinolines. The reactions of these compounds with acryloyl chloride and maleic anhydride produce epoxyisoindolo[2,1-a]quinoline derivatives through successive acylation at the quinoline nitrogen atom and intramolecular exo-[4+2]-cycloaddition at the furan moiety.

  本研究开发了一种氢化呋喃基取代的呋喃并[3,2-c]喹啉、吡喃并[3,2-c]喹啉以及 4-乙氧基和 4-(2-氧代吡咯烷-1-基)喹啉的合成方法。这些化合物与丙烯酰氯和马来酸酐反应，通过喹啉氮原子上的连续酰化和呋喃分子上的分子内外-[4+2]-环加成反应，生成环氧异吲哚并[2,1-a]喹啉衍生物。