(±)-(4aR,5S,10bR)-5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline

• 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: (±)-(4aR,5S,10bR)-5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
• 英文别名: (4aRS,5SR,10bRS)-5-(4-nitro-phenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline；trans-5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline；5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline；(4aR,5S,10bR)-5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: NDJCGDRWPQSLRR-NXHRZFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 (4-硝基苄基亚基)苯胺 在 hydroxyapatite 、 三氯化锑 作用下， 以 乙腈 为溶剂， 生成 (±)-(4aR,5S,10bR)-5-(4-nitrophenyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
  参考文献：
  名称：

  Antimony chloride doped on hydroxyapetite catalyzed stereoselective one-pot synthesis of pyrano[3,2-c]quinolines

  摘要：

  Antimony chloride doped on hydroxyapetite (SbCl3-HAP) has been shown to be an efficient catalyst for the one-pot stereoselective synthesis of trans-pyrano[3,2-c]quinolines from anilines, benzaldehydes and 3,4-dihydro-2H-pyran (DHP). The catalyst was recoverable and reusable. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.007

文献信息

• An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines­
  作者：Cristina Cimarelli、Samuele Bordi、Pamela Piermattei、Maura Pellei、Fabio Del Bello、Enrico Marcantoni

  DOI：10.1055/s-0036-1589104

  日期：2017.12

  is expanded to the one-pot synthesis of N-alkyltetrahydroquinolines through a very efficient iminium-Povarov approach. A deeper insight on the reaction system was provided by the study on the side reactions occurring in the reaction conditions and on the nature of the stereoselectivity. An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through

  摘要 描述了一种通过路易斯酸活化的Povarov反应一锅立体控制合成四氢喹啉的简便有效的合成方法。该方案利用了非常便宜，易于操作且环保的三氯化铈作为催化剂的优势，并允许在溶剂或无溶剂条件下进行反应，从而以良好的选择性获得最终四氢喹啉的反-或顺-异构体。 。反应范围扩大到一锅法合成N-烷基四氢喹啉通过非常有效的亚胺-Povarov方法。通过对在反应条件下发生的副反应和立体选择性的性质的研究，对反应体系有了更深入的了解。 描述了一种通过路易斯酸活化的Povarov反应一锅立体控制合成四氢喹啉的简便有效的合成方法。该方案利用了非常便宜，易于操作且环保的三氯化铈作为催化剂的优势，并允许在溶剂或无溶剂条件下进行反应，从而以良好的选择性获得最终四氢喹啉的反-或顺-异构体。 。反应范围扩大到一锅法合成N-烷基四氢喹啉通过非常有效的亚胺-Povarov方法。通过对在反应条件下发生的副反应和立体选择性的性质的研究，对反应体系有了更深入的了解。
• Simple and practical synthesis of pyrano- and furano[3,2-c]-quinoline derivatives under non-Lewis acid catalysis
  作者：Rui Huan Liu、Xin Yu、Liang Hu、Nie Fang Yu

  DOI：10.1016/j.cclet.2012.06.035

  日期：2012.9

  One-pot synthesis of substituted pyrano- and furano[3,2-c]quinoline derivatives from appropriately substituted anilines, substituted benzaldehydes and dienophiles via Povarov reaction catalyzed by HCl–ethanol were reported. Good to excellent yields with high diastereoselectivity were obtained in all entries tested.

  的一锅法合成取代的吡喃并与呋喃并[3,2- c ^ ]喹啉从适当取代的苯胺，取代的苯甲醛和亲双烯体的衍生物通过通过HCl-乙醇催化波瓦罗夫反应的报道。在所有测试的样品中均获得了具有高非对映选择性的良好至优异的收率。
• Ceric Ammonium Nitrate (CAN)–Catalyzed, Efficient, One-Pot, Three-Component, aza-Diels–Alder Reactions for a Facile Synthesis of Tetrahydropyranoquinoline Derivatives
  作者：Ravinder Goud Puligoundla、Hanmanth Reddy Vulupala、Nagaiah Kommu、Sudhakar Babu Kondra

  DOI：10.1080/00397911.2014.956366

  日期：2015.2.16

  Abstract A simple, efficient, and cost-effective method for the synthesis of tetrahydropyranoquinoline derivatives by a one-pot condensation of aromatic aldehyde, aromatic amine, and 3,4-dihydro-2H-pyran respectively in the presence of ceric ammonium nitrate (CAN) has been described. GRAPHICAL ABSTRACT

  摘要 在硝酸铈铵 (CAN) 存在下，通过芳香醛、芳香胺和 3,4-二氢-2H-吡喃的一锅缩合反应合成四氢吡喃喹啉衍生物的一种简单、高效且经济的方法。 ) 进行了描述。图形概要
• Imino Diels–Alder reactions: One-pot synthesis of tetrahydroquinolines
  作者：Vinod T. Kamble、Bhaskar S. Davane、Sanjay A. Chavan、Dnyanoba B. Muley、Sandeep T. Atkore

  DOI：10.1016/j.cclet.2009.11.016

  日期：2010.3

  Abstract An efficient synthesis of tetrahydroquinoline derivatives is reported via three component coupling reactions of aldehydes and anilines with various dienophiles in the presence of a catalytic amount of perchloric acid adsorbed on silica gel (HClO 4 –SiO 2 ) under mild reaction conditions.

  摘要：在温和的反应条件下，在催化量的高氯酸吸附在硅胶上（HClO 4 -SiO 2）的情况下，醛和苯胺与各种亲二烯体的三组分偶联反应可有效合成四氢喹啉衍生物。
• Novel Use of Selectfluor ^TM for the Synthesis of <i>cis</i> ‐Fused Pyrano‐ and Furanotetrahydroquinolines
  作者：J. S. Yadav、B. V. S. Reddy、V. Sunitha、K. S. Reddy

  DOI：10.1002/adsc.200303101

  日期：2003.11

  Aryl imines formed in situ from aryl aldehydes and aromatic amines undergo smooth [4+2] cycloaddition reactions with cyclic enol ethers such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran in the presence of 10 mol % SelectfluorTM in acetonitrile at room temperature to afford pyrano- and furanotetrahydroquinoline derivatives in excellent yields with high endo-selectivity.

  在10 mol％Selectfluor存在下，由芳基醛和芳族胺原位形成的芳基亚胺与环状烯醇醚（如3,4-二氢-2 H-吡喃和2,3-二氢呋喃）进行平稳的[4 + 2]环加成反应。在室温下于乙腈中TM制得吡喃-和呋喃四氢喹啉衍生物，收率高，且具有高的内选择性。