1-((2,4-cis)-2-(4-chlorophenyl)-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)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
• 英文别名: cis-2-(4-chlorophenyl)-4-(2'-oxopyrrolidin-1'-yl)-1,2,3,4-tetrahydroquinoline；cis-2-(4-chlorophenyl)-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline；cis-2-(p-chlorophenyl)-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline；2-(4-chlorophenyl)-1,2,3,4-tetrahydro-4-(2-oxopyrrolidin-1-yl)quinoline；1-[(2S,4S)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
• 化学式: C₁₉H₁₉ClN₂O
• 分子量: 326.826
• InChiKey: RXJPHIVFJQVKCS-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 1-(4-氯苯基)-N-苯基甲亚胺 在 antimony(III) sulfate 作用下， 以 乙腈 为溶剂， 反应 1.33h， 以92%的产率得到1-((2,4-cis)-2-(4-chlorophenyl)-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Imino Diels-Alder Reactions: Efficient Synthesis of 2-Aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by Antimony(III) Sulfate

  摘要：

  Antimony(III) sulfate is found to catalyze the imino Diels-Alder reaction of Schiff's bases with N-vinylpyrrolidin-2-one to afford 2-aryl-4-(2'-oxopyrrolidinyl-1')-1,2,3,4-tetrahydroquinolines. One-pot synthesis of 1,2,3,4-tetrahydroquinolines from 3-nitro benzaldehyde and aromatic amines with N-vinylpyrrolidin-2-one catalyzed by antimony(III) sulfate is also reported. This catalyst is inexpensive, easily available, and it was also found that catalyst could be recovered quantitatively and reused without much loss of catalytic activity.

  DOI：

  10.1007/s00706-007-0777-0

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％。
• Cation Radical Aza-Diels-Alder Reaction between <i>N</i>-Arylimines and <i>N</i>-Vinyllactams: A Facile Synthesis of 4-Lactam-<i>N</i>-yl Tetrahydroquinolines
  作者：Xiaodong Jia、Li Yang、Bing Han、Wei Zhang、Xiaoling Jin、Zhong-Li Liu

  DOI：10.1055/s-2006-942521

  日期：2006.9

  Cycloaddition of N-arylimines with N-vinylpyrrolidin-2-one or N-vinylazepan-2-one was efficiently induced by tris(4-bromophenyl)aminium hexachloroantimonate producing stereoselectively the corresponding cis-2-aryl-4-(2-oxopyrrolidin-1-yl)- or cis-2-aryl-4-(2-oxoazepan-l-yl)tetrahydroquinoline derivative in good yields.

  N-芳基亚胺与 N-vinylpyrrolidin-2-one 或 N-vinylazepan-2-one 的环加成由三（4-溴苯基）六氯锑酸铵有效诱导，立体选择性地产生相应的 cis-2-aryl-4-(2-oxopyrrolidin- 1-yl)-或cis-2-aryl-4-(2-oxoazepan-l-yl)四氢喹啉衍生物，收率良好。
• 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。
• A CAN-initiated aza-Diels–Alder reaction for a facile synthesis of 4-amido-N-yl tetrahydroquinolines
  作者：Bing Han、Xiao-Dong Jia、Xiao-Ling Jin、Yu-Lu Zhou、Li Yang、Zhong-Li Liu、Wei Yu

  DOI：10.1016/j.tetlet.2006.03.083

  日期：2006.5

  Cycloaddition of N-arylimines with N-vinylpyrrolidin-2-one or N-methyl-N-vinylacetamide was efficiently initiated by cerium(IV) ammonium nitrate (CAN), and produced stereoselectively the corresponding 2,4-cis-4-amido-N-yl tetrahydroquinoline derivatives in good yields.

  的环加成Ñ与-arylimines Ñ -vinylpyrrolidin -2-酮或ñ甲基ñ -vinylacetamide被有效通过铈（IV）铵（CAN），发起并立体选择性产生相应的2,4-顺式-4-酰氨基N-基四氢喹啉衍生物收率高。