(3aα,4α,9bα)-2,3,3a,9b-tetrahydro-9-chloro-5-phenyl-2H-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: (3aα,4α,9bα)-2,3,3a,9b-tetrahydro-9-chloro-5-phenyl-2H-furo[3,2-c]quinoline
• 英文别名: trans-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro<3,2-c>quinoline；trans-8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro<3,2-c>quinoline；8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinolone；trans-8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline；8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuran[3,2-c]quinoline；(3aR,4S,9bR)-8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• 化学式: C₁₇H₁₆ClNO
• 分子量: 285.773
• InChiKey: FNZXKBQNQHNXPH-KBRIMQKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  2

反应信息

• 作为产物：
  描述：

  对氯苯胺 以 乙腈 为溶剂， 生成 (3aS,4S,9bS)-8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline 、 (3aα,4α,9bα)-2,3,3a,9b-tetrahydro-9-chloro-5-phenyl-2H-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

• 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。
• 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。
• A Facile and Convenient Three-component Coupling Protocol for the Synthesis of Pyrano and Furoquinolines
  作者：N. Ravindranath、C. Ramesh、M. Ravinder Reddy、Biswanath Das

  DOI：10.1246/cl.2003.222

  日期：2003.3

  Ceric ammonium nitrate (CAN) catalyzes efficiently the coupling of anilines, benzaldehydes and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran to form the corresponding pyrano or furoquinolines in short reaction times and in high yields.

  硝酸铈铵（CAN）可高效催化苯胺、苯甲醛和3,4-二氢-2H-吡喃或2,3-二氢呋喃的偶联反应，在短时间内以高收率生成相应的吡喃或呋喃喹啉。
• Niobium Pentachloride Catalyzed Multicomponent Povarov Reaction
  作者：Luiz da Silva-Filho、Bruno da Silva、Lucas Martins

  DOI：10.1055/s-0032-1316587

  日期：2012.8

  A single-step method for the synthesis of furan- and pyranoquinoline derivatives through multicomponent Povarov reactions between aniline derivatives, benzaldehyde and two different enol ethers (2,3-dihydrofuran and 3,4-dihydropyran) using niobium pentachloride as catalyst under mild conditions, providing good yields and high diastereoselectivity, is described.

  在温和条件下，使用五氯化铌作为催化剂，通过苯胺衍生物、苯甲醛和两种不同的烯醇醚（2,3-二氢呋喃和 3,4-二氢吡喃）之间的多组分 Povarov 反应合成呋喃和吡喃喹啉衍生物的一步法，描述了提供良好的产率和高的非对映选择性。