cis-6-bromo-2-phenyl-4-(2'-oxopyrrolidin-1'-yl)-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: cis-6-bromo-2-phenyl-4-(2'-oxopyrrolidin-1'-yl)-1,2,3,4-tetrahydroquinoline
• 英文别名: cis-6-bromo-4-(2-oxopyrrolidin-1-yl)-2-phenyl-1,2,3,4-tetrahydroquinoline；1-[(2S,4S)-6-bromo-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
• 化学式: C₁₉H₁₉BrN₂O
• 分子量: 371.277
• InChiKey: WQKOGNFGIZYJFZ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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 、 4-bromo-N-[(E)-phenylmethylidene]aniline 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到cis-6-bromo-2-phenyl-4-(2'-oxopyrrolidin-1'-yl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  N-芳基亚胺和 N-乙烯基内酰胺之间的阳离子自由基氮杂-狄尔斯-阿尔德反应：4-内酰胺-N-基四氢喹啉的简便合成

  摘要：

  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。

  DOI：

  10.1055/s-2006-942521

文献信息

• 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。
• 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.
• Imino Diels-Alder Reactions: Efficient Synthesis of 2-Aryl-4-(2′-oxopyrrolidinyl-1′)-1,2,3,4-tetrahydroquinolines catalyzed by Antimony(III) Sulfate
  作者：Aswathanarayana Srinivasa、Kittappa M. Mahadevan、Vijaykumar Hulikal

  DOI：10.1007/s00706-007-0777-0

  日期：2008.3

  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.
• 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.