1-((2,4-cis)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one

• 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: 1-((2,4-cis)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
• 英文别名: cis-6-methoxy-4-(2-oxopyrrolidin-1-yl)-2-phenyl-1,2,3,4-tetrahydroquinoline；1,2,3,4-tetrahydro-6-methoxy-4-(2-oxopyrrolidin-1-yl)-2-phenylquinoline；1-[(2S,4S)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: ZYZYMJOHZRPZFS-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 4-methoxy-N-[(E)-phenylmethylidene]aniline 在 nitrosonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到1-((2,4-cis)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
  参考文献：
  名称：

  氮（NO +）引发和阳离子自由基介导的亚氨基Diels-Alder反应

  摘要：

  使用四氟硼酸亚硝鎓作为阳离子自由基引发剂，可以实现N-芳基丙氨酸与N-乙烯基吡咯烷酮的有效aza-Diels-Alder反应，得到不同产率的顺式-4-（2-氧吡咯烷基-1-基）四氢喹啉。

  DOI：

  10.1016/j.tetlet.2005.10.083

文献信息

• Photochemically Promoted Aza-Diels–Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation
  作者：Noriyoshi Arai、Takeshi Ohkuma

  DOI：10.1021/acs.joc.7b00838

  日期：2017.7.21

  Aza-Diels–Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded

  Cr（III）/联吡啶配合物在蓝光照射下可有效催化一系列N-芳基丙氨酸和官能化烯烃之间的Aza-Diels-Alder型环加成反应，得到相应的1,2,3,4-四氢喹啉高产率的非对映异构体衍生物。通常，亚苄基苯胺与1-乙烯基-2-吡咯烷酮的反应在底物与催化剂的摩尔比（S / C）为1000的情况下平稳进行，并在室温（20–25°C）下4小时内完成，从而获得环加成产物的产率为97％。
• Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4‐Tetrahydroquinoline Scaffolds Catalyzed by Helicene‐Viologen Hybrids
  作者：Paul E. Reyes‐Gutiérrez、Tynchtyk T. Amatov、Pavel Švec、Ivana Císařová、David Šaman、Radek Pohl、Filip Teplý、Lubomír Pospíšil

  DOI：10.1002/cplu.202000151

  日期：2020.10

  are structurally linked to helicenes and viologens, and they represent an attractive field of research in chemistry and medicinal chemistry. In the present work they were used as catalysts for the synthesis of 1,2,3,4‐tetrahydroquinolines in good yields by the Povarov reaction. The substrate scope and the capability of different helquats to promote Povarov reactions are demonstrated. Studies to elucidate

  Helquats（HQs）在结构上与螺旋藻和紫罗兰素联系在一起，它们代表了化学和药物化学领域的一个有吸引力的研究领域。在目前的工作中，它们被用作通过Povarov反应以高收率合成1,2,3,4-四氢喹啉的催化剂。证明了底物的范围和不同头盔促进Povarov反应的能力。阐明机理细节的研究表明，盔红素通过阳离子自由基机理充当单电子转移氧化剂。对HQs催化活性的筛选证实，与二茂铁/二茂铁氧化还原对相比，活性HQ必须具有低于-8.67 eV的LUMO能量和标准氧化还原电势（低于负值）高于-1.2V。
• 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。
• Nitrosonium (NO+) initiated and cation radical-mediated imino Diels–Alder reaction
  作者：Yulu Zhou、Xiaodong Jia、Rui Li、Zhengang Liu、Zhongli Liu、Longmin Wu

  DOI：10.1016/j.tetlet.2005.10.083

  日期：2005.12

  An efficient aza-Diels–Alder reaction of N-arylimines with N-vinylpyrrolidinone was achieved using nitrosonium tetrafluoroborate as a cation radical initiator, giving cis-4-(2-oxopyrrolidin-1-yl)tetrahydroquinolines in various yields.

  使用四氟硼酸亚硝鎓作为阳离子自由基引发剂，可以实现N-芳基丙氨酸与N-乙烯基吡咯烷酮的有效aza-Diels-Alder反应，得到不同产率的顺式-4-（2-氧吡咯烷基-1-基）四氢喹啉。
• Mild and Simple Access to Diverse 4-Amino-substituted 2-Phenyl-1,2,3,4-tetrahydroquinolines and 2-Phenylquinolines Based on a Multicomponent Imino Diels–Alder Reaction
  作者：P. Prabhakara Varma、Bailure S. Sherigara、Kittappa M. Mahadevan、Vijaykumar Hulikal

  DOI：10.1080/00397910903221035

  日期：2010.7.12

  A straightforward synthesis of new 1-(2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones/azepan-2-one from N-vinyl caprolactam/N-vinylpyrrolidin-2-one and N-benzylideneaniline via the imino Diels-Alder reaction has been reported for the first time. Antimony(III) chloride has been shown to effectively catalyze imino-Diels-Alder reaction to afford both 2-phenylquinoline and 2-phenyl-1,2,3,4-tetrahydroquinolin derivatives in excellent yields at ambient temperature. The cis diastereoselectivity to give cis 2-phenyl-1,2,3,4-tetrahydroquinolines is also highlighted in this reaction.