3,4,4a,5,6,10b-hexahydro-5-phenyl-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: 3,4,4a,5,6,10b-hexahydro-5-phenyl-2H-pyrano[3,2-c]quinoline
• 英文别名: (4aS,10bS)-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: NNBCJSIAXXSBNX-DKKDMOBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 N-苄叉苯胺 以 various solvent(s) 为溶剂， 反应 4.0h， 以91%的产率得到3,4,4a,5,6,10b-hexahydro-5-phenyl-2H-pyrano[3,2-c]quinoline
  参考文献：
  名称：

  Aza-Diels–Alder reaction in fluorinated alcohols. A one-pot synthesis of tetrahydroquinolines

  摘要：

  Hexafluoroisopropanol and trifluoroethanol are found to promote imino-Diels-Alder reactions of the N-aryl aldimine 1 with alkyl vinyl ethers to afford the corresponding tetrahydroquinolines in good yields without Lewis acid under mild and neutral conditions. The reaction is also efficient in a three component process from aldehyde, amine and vinyl ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02558-3

文献信息

• TMSCl-Catalyzed Aza-Diels-Alder Reaction: A Simple and Efficient ­Synthesis of Pyrano- and Furanoquinolines
  作者：Ching-Fa Yao、Shivaji More、M. Sastry

  DOI：10.1055/s-2006-939711

  日期：2006.6

  An efficient TMSCl-catalyzed synthesis of pyrano- and furanoquinolines and phenanthridinone derivative has been developed. In the presence of TMSCl (20 mol%), various aliphatic, ­aromatic and heteroaromatic aldehydes reacted with different anilines in the presence of either 2,3-dihydrofuran, 3,4-dihydro-2H-pyran or cyclohexenone to afford the aza-Diels-Alder adducts in excellent yield at room temperature. The ambient conditions, fast reaction rates, and excellent product yields are important characteristics of this reaction.

  我们开发了一种高效的 TMSCl 催化合成吡喃喹啉、呋喃喹啉和菲啶酮衍生物的方法。在 2,3-二氢呋喃、3,4-二氢-2H-吡喃或环己酮存在下，各种脂肪族、芳香族和杂芳香族醛与不同的苯胺发生反应，在室温下以极好的收率得到偶氮-Diels-Alder 加合物。该反应的重要特点是环境条件好、反应速度快、产物收率高。
• Magnesium Perchlorate: An Efficient Catalyst for One-Pot Synthesis of Pyrano- and Furanoquinolines
  作者：Vinod Kamble、Vijaymala Ekhe、Neeta Joshi、Ankush Biradar

  DOI：10.1055/s-2007-980354

  日期：2007.6

  The pyranoquinoline moiety is a structural feature of many natural products. By using a reaction of anilines, aldehydes and 3,4-dihydro-2H-pyran or 2,3-dihydrofuran catalyzed by trace amount of magnesium perchlorate at room temperature, various pyrano- and furanoquinoline derivatives were synthesized efficiently. The noteworthy features of the present system are mild conditions, shorter reaction time, and high diastereoselectivity.

  吡喃喹啉是许多天然产物的结构特征之一。在微量高氯酸镁的催化下，利用苯胺、醛和 3,4-二氢-2H-吡喃或 2,3-二氢呋喃在室温下的反应，高效合成了各种吡喃和呋喃喹啉衍生物。该体系的显著特点是条件温和、反应时间短、非对映选择性高。
• UREA NITRATE CATALYZED IMINO DIELS-ALDER REACTIONS: SYNTHESIS OF CYCLOPENTAQUINOLINES, PYRANOQUINOLINES, AND FUROQUINOLINE DERIVATIVES
  作者：Marimuthu Anniyappan、Rajagopal Nagarajan、Paramasivan T. Perumal

  DOI：10.1081/scc-120001514

  日期：2002.1.1

  ABSTRACT Urea nitrate is found to be an efficient catalyst for the imino Diels-Alder reaction of aldimines with cyclopentadiene, 3,4-dihydropyran and dihydrofuran is reported for the first time. One pot synthesis of cyclopentaquinolines from benzaldehyde, aromatic amines with cyclopentadiene catalyzed by urea nitrate is also reported.

  摘要 硝酸尿素被发现是醛亚胺与环戊二烯、3,4-二氢吡喃和二氢呋喃的亚氨基Diels-Alder 反应的有效催化剂，这是首次报道。还报道了由苯甲醛、芳香胺与硝酸尿素催化的环戊二烯一锅合成环戊喹啉。
• The preparation of new enantiopure imidazolinium salts and their evaluation as catalysts and shift reagents
  作者：Václav Jurčík、René Wilhelm

  DOI：10.1016/j.tetasy.2006.02.021

  日期：2006.3

  A series of new chiral imidazolinium salts were prepared and tested as catalysts. It was possible to show that bis-imidazolinium salts had a higher reactivity than mono-imidazolium salts. In addition a chiral discrimination of the bis-imidazolinium salts with the potassium salt of racemic Mosher's acid wits proven by NMR studies. (c) 2006 Elsevier Ltd. All rights reserved.
• Aza-Diels–Alder reaction in fluorinated alcohols. A one-pot synthesis of tetrahydroquinolines
  作者：Maria Vittoria Spanedda、Vu Dinh Hoang、Benoit Crousse、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1016/s0040-4039(02)02558-3

  日期：2003.1

  Hexafluoroisopropanol and trifluoroethanol are found to promote imino-Diels-Alder reactions of the N-aryl aldimine 1 with alkyl vinyl ethers to afford the corresponding tetrahydroquinolines in good yields without Lewis acid under mild and neutral conditions. The reaction is also efficient in a three component process from aldehyde, amine and vinyl ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.