trans-4-(carbazol-9-yl)-2-(p-methoxyphenyl)-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)-2-(p-methoxyphenyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 9-[(2S,4R)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-4-yl]carbazole
• 化学式: C₂₈H₂₄N₂O
• 分子量: 404.511
• InChiKey: XVBLFINAHAMNMO-LBNVMWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 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：
  26.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基咔唑 、 (E)-N-(4-methoxybenzylidene)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)-2-(p-methoxyphenyl)-1,2,3,4-tetrahydroquinoline 、 trans-4-(carbazol-9-yl)-2-(p-methoxyphenyl)-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

• Tetrahydroquinoline syntheses induced with catalytic amounts of viologen additives
  作者：Zheng Xue、Anindya Samanta、Bruce R. Whittlesey、Michael F. Mayer

  DOI：10.1016/j.tetlet.2009.08.058

  日期：2009.11

  The viologen N,N'-dicyanomethyl-4,4'-bipyridinium center dot 2PF(6) was found to induce an aza-Diels-Alder reaction of N-arylimines with N-vinylpyrrolidinone or N-vinylcarbazole, producing tetrahydroquinoline derivatives with high cis/trans selectivities and yields. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.