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

• 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)-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 英文别名: (3aR,4R,9bR)-4-(furan-2-yl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: ZQRYWYRQXPVNFH-DFBGVHRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (3aSR,4SR,9bSR)-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以84%的产率得到2'-[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)-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。
• Perhydrofuro[3,2-c]-, perhydropyrano[3,2-c]-, and 4-ethoxy-2-(5-R-furan-2-yl)tetrahydroquinolines. Synthesis and transformations
  作者：F. I. Zubkov、V. P. Zaitsev、A. M. Piskareva、M. N. Eliseeva、E. V. Nikitina、N. M. Mikhailova、A. V. Varlamov

  DOI：10.1134/s1070428010080142

  日期：2010.8

  furo[3,2-c]quinolines, pyrano-[3,2-c]quinolines, and 4-ethoxyquinolines were synthesized by the imino Diels-Alder (Povarov) reaction. Cycloadditions of these compounds with maleic, citraconic, and dibromomaleic anhydrides, as well as with acryloyl, methacryloyl, and cinnamoyl chlorides led to the formation of substituted epoxyisoindolo[2,1-a]-quinolines and -quinolinecarboxylic acids. Oxidation of the

  通过氢化合成了部分氢化的2- [5-甲基（溴，硝基）呋喃-2-基]取代的呋喃[3,2- c ]喹啉，吡喃-[3,2- c ]喹啉和4-乙氧基喹啉。亚氨基Diels-Alder（Povarov）反应。这些化合物与马来酸酐，柠康酸酐和二溴马来酸酐以及丙烯酰，甲基丙烯酰和肉桂酰氯的环加成反应导致形成取代的环氧异吲哚并[2,1- a ]-喹啉和-喹啉羧酸。完成了加合物中双C = C键的氧化，羧基的酯化和7-氧杂双环庚烯片段的芳构化。
• TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient ­Synthesis of Pyrano- and Furanoquinolines
  作者：Ching-Fa Yao、Shivaji More、M. Sastry

  DOI：10.1055/s-2006-939711

  日期：2006.6

  An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, ­aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.

  我们开发了一种高效的 TMSCl 催化合成吡喃喹啉、呋喃喹啉和菲啶酮衍生物的方法。在 2,3-二氢呋喃、3,4-二氢-2H-吡喃或环己酮存在下，各种脂肪族、芳香族和杂芳香族醛与不同的苯胺发生反应，在室温下以极好的收率得到偶氮-Diels-Alder 加合物。该反应的重要特点是环境条件好、反应速度快、产物收率高。
• Ferric sulfate [Fe2(SO4)3·xH2O]: an efficient heterogeneous catalyst for the synthesis of tetrahydroquinoline derivatives using Povarov reaction
  作者：Abu T. Khan、Deb Kumar Das、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2011.06.080

  日期：2011.8

  Fe-2(SO4)(3)center dot xH(2)O can be used as an efficient and reusable catalyst for the synthesis of pyrano- and furanotetrahydroquinolines via one-pot three-component Povarov reaction involving aromatic aldehydes, aromatic amines, and cyclic enol ethers. The catalyst is recyclable, economically viable, and environmentally benign. This protocol provides good yields and diastereoselectivity as well as applicability on a wide range of substrates. (C) 2011 Elsevier Ltd. All rights reserved.
• Controllable stereoselective synthesis of cis or trans pyrano and furano tetrahydroquinolines: Polyaniline-p-toluenesulfonate salt catalyzed one-pot aza-Diels–Alder reactions
  作者：Srinivasan Palaniappan、Boddula Rajender、Male Umashankar

  DOI：10.1016/j.molcata.2011.10.014

  日期：2012.1

  cis as well as trans pyrano tetrahydroquinolines were synthesized using a polymeric solid acid catalyst, polyaniline-p-toluenesulfonate (PANI-PTSA) salt, by conveniently controlling the reaction conditions. One-pot three component aza-Diels-Alder reactions involving aromatic aldehydes, aniline, and 3,4-dihydro-2H-pyran are effectively catalyzed by PANI-PTSA under solvent free condition at room temperature afford cis pyranoquinolines and the reaction carried out at 80 degrees C gave trans configuration. Whereas reactions involving 2,3-dihydrofuran instead of 3,4-dihydro-2H-pyran gave major cis fura-noquinolines under solvent free conditions and 100% cis configuration with the use of solvents. This process conforms to the principles of 'green' chemistry by the usage of solvent free medium, easily handleable, recyclable and eco-friendly nature of the catalyst. In addition, this method provides simple work up procedure, short reaction time and use of easily synthesizable cheaper catalyst. (C) 2011 Elsevier B.V. All rights reserved.