trans-4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydro-furo[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: trans-4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline
• 英文别名: trans-4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline；4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinolone；(3aS,4R,9bS)-4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: PVINMXFJSYSDGX-RYQLBKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 以 乙腈 为溶剂， 生成 cis-4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline 、 trans-4-(4-methoxyphenyl)-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline
  参考文献：
  名称：

  Kaur, Ramneet; Khajuria, Rajni; Saini, Yeshwinder, Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 1, p. 91 - 102

  摘要：

  DOI：

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。
• Halogen Bond‐Catalyzed Povarov Reactions
  作者：Xuelei Liu、Patrick H. Toy

  DOI：10.1002/adsc.202000665

  日期：2020.8.19

  3‐dihydropyrrole. Very high isolated yields of the desired 1,2,3,4‐tetrahydroquinoline products were obtained with low catalyst loadings (0.01 equivalents) and short reaction times (minutes to hours) at ambient temperature. Notably, the bis(benzimidazolium iodide)‐based catalyst used in these reactions proved to be more efficient than analogous bromine and chlorine functionalized compounds, as well as a related

  据报道，使用双齿卤素键供体来催化衍生自芳基醛和苯胺的亚胺的Povarov反应。在这些反应中使用的亲双烯体包括2,3-二氢呋喃，N-乙烯基-2-吡咯烷酮和NCbz保护的2，3-二氢吡咯。在环境温度下，以较低的催化剂负载量（0.01当量）和较短的反应时间（数分钟至数小时）获得了所需1,2,3,4-四氢喹啉产物的很高的分离产率。值得注意的是，在这些反应中使用的基于双（碘化咪唑鎓）的催化剂被证明比类似的溴和氯官能化化合物以及相关的单齿碘化亚苄基碘更有效。这些观察结果与其他人关于卤素键有机催化的报道相似，随着该领域的发展，可能对指导催化剂设计很有用。
• 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。
• Novel and Efficient Lewis Acids as Catalysts for Single-step Synthesis of Pyrano- and Furoquinolines
  作者：Biswanath Das、M. Ravinder Reddy、V. Saidi Reddy、R. Ramu

  DOI：10.1246/cl.2004.1526

  日期：2004.11

  Some Lewis acids such as ZrCl4, SnCl4, TiCl4, and PtCl4 have been found to be novel and highly efficient catalysts for one-pot coupling of the three components, anilines, aldehydes, and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran to produce the corresponding pyrano- or furoqinolines in high yields and high diastereoselectivity.

  研究发现，一些路易斯酸（如 ZrCl4、SnCl4、TiCl4 和 PtCl4）是新型高效催化剂，可用于苯胺、醛和 3,4-二氢-2H-吡喃或 2,3-二氢呋喃这三种成分的一锅耦合，以高产率和高非对映选择性生成相应的吡喃或呋喃喹啉类化合物。
• 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。