trans-4-(carbazol-9-yl)-6-methoxy-2-(p-nitrophenyl)-1,2,3,4-tetrahydroquinoline

• 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-(carbazol-9-yl)-6-methoxy-2-(p-nitrophenyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 9-[(2S,4R)-6-methoxy-2-(4-nitrophenyl)-1,2,3,4-tetrahydroquinolin-4-yl]carbazole
• 化学式: C₂₈H₂₃N₃O₃
• 分子量: 449.509
• InChiKey: SFZGLFVBVMAZPA-LBNVMWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙烯基咔唑 、 (E)-4-methoxy-N-(4-nitrobenzylidene)aniline 在 2,4,6-triphenylpyrylium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 cis-4-(carbazol-9-yl)-6-methoxy-2-(p-nitrophenyl)-1,2,3,4-tetrahydroquinoline 、 trans-4-(carbazol-9-yl)-6-methoxy-2-(p-nitrophenyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Photochemically catalyzed Diels–Alder reaction of arylimines with N-vinylpyrrolidinone and N-vinylcarbazole by 2,4,6-triphenylpyrylium salt: synthesis of 4-heterocycle-substituted tetrahydroquinoline derivatives

  摘要：

  Photochemically promoted Diels-Alder reactions of N-arylimines with N-vinylpyrrolidinone and N-vinylcarbazole were achieved by using 2,4,6-triphenylpyrylium tetrafluoroborate as a catalyst to produce corresponding 2-oxopyrrolidin-1-yl and carbazol-9-yltetrahydroquinolines in high yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.042

文献信息

• 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。
• Photochemically catalyzed Diels–Alder reaction of arylimines with N-vinylpyrrolidinone and N-vinylcarbazole by 2,4,6-triphenylpyrylium salt: synthesis of 4-heterocycle-substituted tetrahydroquinoline derivatives
  作者：Wei Zhang、Yanping Guo、Zhengang Liu、Xiaoling Jin、Li Yang、Zhong-Li Liu

  DOI：10.1016/j.tet.2004.11.042

  日期：2005.1

  Photochemically promoted Diels-Alder reactions of N-arylimines with N-vinylpyrrolidinone and N-vinylcarbazole were achieved by using 2,4,6-triphenylpyrylium tetrafluoroborate as a catalyst to produce corresponding 2-oxopyrrolidin-1-yl and carbazol-9-yltetrahydroquinolines in high yields. (C) 2004 Elsevier Ltd. All rights reserved.