(3aS,4S,9bS)-8-chloro-4-phenyl-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: (3aS,4S,9bS)-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-XKQJLSEDSA-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：

  在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (3aS,4S,9bS)-8-chloro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
  参考文献：
  名称：

  Prato, Maurizio; Scorrano, Gianfranco; Stivanello, Mariano, Gazzetta Chimica Italiana, 1988, vol. 118, # 11, p. 797 - 798

  摘要：

  DOI：

文献信息

• Sodium Salts of Anionic Chiral Cobalt(III) Complexes as Catalysts of the Enantioselective Povarov Reaction
  作者：Jie Yu、Hua-Jie Jiang、Ya Zhou、Shi-Wei Luo、Liu-Zhu Gong

  DOI：10.1002/anie.201504790

  日期：2015.9.14

  The sodium salts of anionic chiral cobalt(III) complexes (CCC−Na+) have been found to be efficient catalysts of the asymmetric Povarov reaction of easily accessible dienophiles, such as 2,3‐dihydrofuran, ethyl vinyl ether, and an N‐protected 2,3‐dihydropyrrole, with 2‐azadienes. Ring‐fused tetrahydroquinolines with up to three contiguous stereogenic centers were thus obtained in high yields, excellent

  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。
• 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。
• Tungstophosphoric Acid–Catalyzed Imino-Diels–Alder Reaction: An Efficient One-Pot Synthesis of Pyrano- and Furanoquinoline Derivatives
  作者：Biswanath Das、P. Balasubramanyam、Maddeboina Krishnaiah、Boyapati Veeranjaneyulu

  DOI：10.1080/00397910902838946

  日期：2009.10.12

  Abstract Tungstophosphoric acid has been found to be an efficient catalyst for the synthesis of pyranos- and furanoquinolines through the Imino-Diels–Alder reaction involving one-pot coupling of benzaldehydes, anilines, and 3,4-dihydro-2 H-pyran or 2,3-dihydrofuran. The products are formed at room temperature in excellent yields in a short period of time.

  摘要 磷酸钨酸是通过亚氨基-狄尔斯-阿尔德反应合成吡喃和呋喃喹啉的有效催化剂，该反应涉及苯甲醛、苯胺和 3,4-二氢-2 H-吡喃或 2 ,3-二氢呋喃。产品在室温下以极好的产率在短时间内形成。
• 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。
• Simple and practical synthesis of pyrano- and furano[3,2-c]-quinoline derivatives under non-Lewis acid catalysis
  作者：Rui Huan Liu、Xin Yu、Liang Hu、Nie Fang Yu

  DOI：10.1016/j.cclet.2012.06.035

  日期：2012.9

  One-pot synthesis of substituted pyrano- and furano[3,2-c]quinoline derivatives from appropriately substituted anilines, substituted benzaldehydes and dienophiles via Povarov reaction catalyzed by HCl–ethanol were reported. Good to excellent yields with high diastereoselectivity were obtained in all entries tested.

  的一锅法合成取代的吡喃并与呋喃并[3,2- c ^ ]喹啉从适当取代的苯胺，取代的苯甲醛和亲双烯体的衍生物通过通过HCl-乙醇催化波瓦罗夫反应的报道。在所有测试的样品中均获得了具有高非对映选择性的良好至优异的收率。