cis-4-(4-fluorophenyl)-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: cis-4-(4-fluorophenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 英文别名: (3aS,4S,9bS)-4-(4-fluorophenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 化学式: C₁₇H₁₆FNO
• 分子量: 269.319
• InChiKey: VYXWNIZYJSGXNA-USXIJHARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 对氟苯甲醛 、 苯胺 在 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 3.5h， 以89%的产率得到cis-4-(4-fluorophenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  离子液体中的Aza-Diels-Alder反应：吡喃和呋喃喹啉的简便合成

  摘要：

  发现室温离子液体可在温和便捷的条件下有效催化醛，胺和环状烯醇醚（例如3,4-二氢-2 H-吡喃和2,3-二氢呋喃）的三组分偶联反应，从而提供相应的吡喃基和呋喃基喹啉具有优异的收率和较高的内选择性。有趣的是，2，3-二氢呋喃在相似的反应条件下选择性地提供了内产物。

  DOI：

  10.1016/s0040-4020(03)00027-9

文献信息

• Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers <i>via</i> Oxidation/Aza‐Diels‐Alder Cycloaddition
  作者：Vera A. Vil'、Sergei S. Grishin、Elena P. Baberkina、Anna L. Alekseenko、Alexey P. Glinushkin、Alexey E. Kovalenko、Alexander O. Terent'ev

  DOI：10.1002/adsc.202101355

  日期：2022.3.15

  Electrochemical synthesis of cyclic ether-annulated tetrahydroquinolines from imines and cyclic ethers in an undivided cell under constant current conditions was developed. The electrosynthesis proceeds via the enol ether formation from ethers following the aza-Diels-Alder [4+2] cycloaddition. The method is applicable to a wide range of imines and results in the desired products in yields of 23 to

  开发了在恒流条件下在未分裂电池中由亚胺和环醚电化学合成环醚环化四氢喹啉。在 aza-Diels-Alder [4+2] 环加成之后，通过醚形成烯醇醚进行电合成。该方法适用于多种亚胺，并以 23% 至 75% 的收率得到所需产物。从相应的苯胺和醛原位制备亚胺导致四氢喹啉的产率基本相同。使用化学氧化剂没有形成环加成产物。合成的环醚环化四氢喹啉具有较高的抗真菌活性，优于市售杀菌剂三唑酮。
• Radical Cation Salts Induced aza-Diels-Alder Reaction: Synthesis of Hexahydrofuro[3,2-c]- quinoline Derivatives
  作者：Zhong Jia、Yan Ren、Cong-De Huo、Xiang-Ning Chen、Chong-Xiang Tong、Xiao-Dong Jia

  DOI：10.2174/157017812800167484

  日期：2012.3.1

  Aza-Diels-Alder reaction between imines and 2,3-dihydrofuran under radical cation induced conditions was achieved and series of hexahydrofuro[3,2-c]quinoline derivatives was prepared. The stereoselectivity was affected by the substituents on imines, which revealed a stepwise mechanism. A radical cation mediated mechanism was proposed to rationalize the formation of the products.

  亚胺与2,3-二氢呋喃在自由基阳离子诱导的条件下进行了Aza-Diels-Alder反应，制备了一系列六氢呋喃[3,2-c]喹啉衍生物。立体选择性受亚胺上取代基的影响，这揭示了一种逐步机理。提出了自由基阳离子介导的机理以合理化产物的形成。
• Samarium Triflate as Mild and Efficient Catalyst for Aza-Diels–Alder Reaction: A Facile Synthesis of<i>cis</i>-Fused Pyrano- and Furanoquinolines
  作者：A. Venkat Narsaiah、A. Ramesh Reddy、B. V. Subba Reddy、J. S. Yadav

  DOI：10.1080/00397910903161736

  日期：2010.5.19

  Three-component coupling reactions of aldehydes, amines, and cyclic enol ethers have been carried out in the presence of samarium triflate to afford the corresponding pyrano and furanoquinolines in excellent yields with high endo-selectivity. The reaction conditions are mild and amenable to scale-up.

  醛、胺和环烯醇醚的三组分偶联反应在三氟甲磺酸钐存在下进行，以优异的收率和高内向选择性提供相应的吡喃并呋喃喹啉。反应条件温和，易于放大。
• Phosphomolybdic acid-catalyzed efficient one-pot three-component aza-Diels–Alder reactions under solvent-free conditions: a facile synthesis of trans-fused pyrano- and furanotetrahydroquinolines
  作者：K. Nagaiah、D. Sreenu、R. Srinivasa Rao、G. Vashishta、J.S. Yadav

  DOI：10.1016/j.tetlet.2006.04.085

  日期：2006.6

  furanotetrahydroquinoline derivatives have been synthesized via a one-pot three-component aza-Diels–Alder reaction of aryl imines formed in situ from aromatic amines and arylaldehydes with cyclic enol ethers,such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran,in the presence of 1 mol % of phosphomolybdic acid under solvent-free conditions at room temperature in good to excellent yields.

  通过一锅三组分aza-Diels-Alder反应合成了反式吡喃-呋喃和呋喃四氢喹啉衍生物，该反应由芳族胺和芳醛与环烯醇醚（如3,4-二氢-2）在原位形成，在室温下在无溶剂条件下，在1摩尔％的磷钼酸存在下，H-吡喃和2,3-二氢呋喃具有良好的收率。
• Aza-Diels–Alder reactions in ionic liquids: a facile synthesis of pyrano- and furanoquinolines
  作者：J.S Yadav、B.V.S Reddy、J.S.S Reddy、R.Srinivasa Rao

  DOI：10.1016/s0040-4020(03)00027-9

  日期：2003.2

  efficiently the three component-coupling reactions of aldehydes, amines and cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under mild and convenient conditions to afford the corresponding pyrano- and furanoquinolines in excellent yields with high endo-selectivity. Interestingly, 2,3-dihydrofuran afforded selectively endo-products under the similar reaction conditions.

  发现室温离子液体可在温和便捷的条件下有效催化醛，胺和环状烯醇醚（例如3,4-二氢-2 H-吡喃和2,3-二氢呋喃）的三组分偶联反应，从而提供相应的吡喃基和呋喃基喹啉具有优异的收率和较高的内选择性。有趣的是，2，3-二氢呋喃在相似的反应条件下选择性地提供了内产物。