endo-4-(4-chlorophenyl)-8-methyl-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: endo-4-(4-chlorophenyl)-8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 英文别名: cis-4-(4-chlorophenyl)-8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline；cis-4-(4-chlorophenyl)-9-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline；cis-4-(4-chlorophenyl)-8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2c]quinoline；4-(4-chlorophenyl)-8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline；(3aR,4R,9bR)-4-(4-chlorophenyl)-8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 化学式: C₁₈H₁₈ClNO
• 分子量: 299.8
• InChiKey: MNHMPXMMVFDLAR-FHLIZLRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 N-(4-氯亚苄基)-4-甲基苯胺 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 endo-4-(4-chlorophenyl)-8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  阴离子手性钴（III）配合物的钠盐作为对映选择性Povarov反应的催化剂

  摘要：

  阴离子手性钴的钠盐（III）配合物（CCC -钠+）已经被发现是容易接近亲双烯体的不对称波瓦罗夫反应的高效催化剂，如2,3-二氢呋喃，乙基乙烯基醚，和Ñ -受保护的2,3-二氢吡咯和2-氮杂二烯。从而以高收率，出色的非对映选择性（内/外最高> 20：1）和高对映选择性（最高95：5 er）获得了具有多达三个连续立体中心的环稠合四氢喹啉。

  DOI：

  10.1002/anie.201504790

文献信息

• LiBF₄-Catalyzed Imino-Diels-Alder Reaction: A Facile Synthesis of Pyrano- and Furoquinolines
  作者：Jhillu Yadav、Basi Subba Reddy、Chinti Rheddy Madhuri、Gowravaram Sabitha

  DOI：10.1055/s-2001-14904

  日期：——

  Lithium tetrafluoroborate efficiently catalyzes the imino-Diels-Alder reaction of aldimines with 3,4-dihydro-2H-pyran (DHP) and 2,3-dihydrofuran to afford the corresponding pyrano- and furoquinolines in high yields with high diastereoselectivity.

  四氟硼酸锂有效催化醛亚胺与 3,4-二氢-2 H-吡喃 (DHP) 和 2,3-二氢呋喃的亚氨基-Diels-Alder 反应，以高收率和高非对映选择性提供相应的吡喃和呋喃喹啉。
• 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。
• 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。
• An Efficient One-Pot Synthesis of Pyrano- and Furoquinolines Employing Two Reusable Solid Acids as Heterogeneous Catalysts
  作者：Biswanath Das、K. V. Srinivas

  DOI：10.1055/s-2004-829576

  日期：——

  Two solid acids, Fe 3 + -K-10 montmorillonite clay and HY-zeolite have been employed efficiently for single-step synthesis of pyrano- or furoquinolines in high yields and high diastereoselectivities by coupling of three components: anilines, benzaldehydes and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran. Both the heterogeneous catalysts are recoverable and recyclable.

  两种固体酸 Fe 3 + -K-10 蒙脱石粘土和 HY-沸石已被有效地用于单步合成吡喃喹啉或呋喃喹啉，通过将三种组分偶联，高产率和高非对映选择性：苯胺、苯甲醛和 3,4 -二氢-2H-吡喃或2,3-二氢呋喃。两种多相催化剂都是可回收和再循环的。
• 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。