ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl (2S,6R)-4-(4-bromoanilino)-1-(4-bromophenyl)-2,6-bis(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₄H₃₂Br₂N₂O₄
• 分子量: 692.447
• InChiKey: CQOGPKGCUGVVJW-CQTOTRCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-甲氧基苯甲醛 、 4-溴苯胺 在 nano-Al₂O₃/BF₃/Fe₃O₄ 作用下， 以 neat (no solvent) 为溶剂， 反应 3.5h， 以82%的产率得到ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  以纳米Al 2 O 3 / BF 3 / Fe 3 O 4为高效纳米催化剂，一锅法合成五个取代的四氢吡啶

  摘要：

  摘要合成了一种 纳米Al 2 O 3 / BF 3 / Fe 3 O 4催化剂，它是一种高效，可重复使用的催化剂。合成的磁性催化剂已经通过多种方法表征，例如FT-IR，FESEM，TGA，TEM，VSM，XRF，XRD和BET。该催化剂不需要特别的预防措施来制备，处理或储存，并且可以在环境温度下储存数月而不会失去催化活性。五取代的四氢吡啶及其衍生物具有令人感兴趣的一类药物活性。因此，纳米Al 2 O 3 / BF 3 / Fe 3 O 4该催化剂用于在无溶剂条件下通过芳族醛，苯胺和β-酮酸酯的一锅多组分反应制备五取代的四氢吡啶。通过傅里叶变换光谱和核磁共振研究了产物的结构。本方案具有易于纯化，清洁和方便的程序以及分离产物的高产率的显着优点。此外，该催化剂可以循环使用几次而不会降低其令人赞叹的活性。 图形概要

  DOI：

  10.1007/s11164-018-3320-5

文献信息

• Nano-TiCl4/SiO2: An efficient heterogeneous solid acid catalyst for the one pot cascade five-component synthesis of densely functionalized tetrahydropyridines
  作者：ABDOLHAMID BAMONIRI、BI BI FATEMEH MIRJALILI、REZA TARAZIAN

  DOI：10.1007/s12039-015-0845-7

  日期：2015.5

  Nano-TiCl4/SiO2 was found to be an inexpensive and efficient heterogeneous solid acid catalyst for the synthesis of one-pot cascade synthesis of highly functionalized asymmetric tetrahydropyridines from the five-component condensation reaction of the para-substituted anilines and aromatic aldehydes with ethyl acetoacetate under thermal conditions. Novel methodology, environmentally benign conditions

  发现纳米-TiCl 4 / SiO 2是一种廉价且有效的非均相固体酸催化剂，用于通过对位取代苯胺和芳族醛与亚胺的五组分缩合反应一锅级联合成高度官能化的不对称四氢吡啶。在热条件下乙酰乙酸乙酯。新颖的方法，对环境无害的条件，清洁的方案，易于操作和高收率是该方案的重要优点。使用物理和光谱数据（例如FT-IR，1 H-NMR和某些情况下的13 C-NMR和CHN分析）对产物进行表征。 发现纳米-TiCl 4 / SiO 2是一种廉价且有效的多相固体酸催化剂，用于通过对位取代的苯胺和苯甲醛与乙基的五组分缩合反应合成一锅级联合成高度官能化的不对称四氢吡啶。在热条件下乙酰乙酸。
• Nanomagnetically modified ferric hydrogen sulfate (NiFe2O4@SiO2-FHS): a reusable green catalyst for the synthesis of highly functionalized piperidine derivatives
  作者：Mohammad Rahimizadeh、Seyed Mohammad Seyedi、Mohsen Abbasi、Hossein Eshghi、Amir Khojastehnezhad、Farid Moeinpour、Mehdi Bakavoli

  DOI：10.1007/s13738-014-0546-z

  日期：2015.5

  An efficient and one-pot multi-component procedure for the preparation of functionalized piperidine derivatives from reactions of aromatic aldehydes, substituted anilines and ethyl acetoacetate in the presence of ferric hydrogen sulfate-supported silica-coated magnetic nanoparticles (NiFe2O4@SiO2-FHS) as a magnetically recyclable green catalyst has been developed. The catalysts show environmentally benign character, which can be easily prepared, stored, and recovered several times without obvious significant loss of activity.

  开发了一种高效的一锅多组分程序，通过在含有铁氢硫酸盐支持的硅涂层磁性纳米颗粒（NiFe2O4@SiO2-FHS）作为磁性可回收绿色催化剂的条件下，利用芳香醛、取代苯胺和乙酰乙酸乙酯的反应制备功能化哌啶衍生物。这些催化剂显示出环境友好的特性，易于制备、存储，并且可以多次回收而不会显著降低活性。
• A Facile and Efficient Solid Supported, One-Pot Synthesis of Functionalized Piperidine Derivatives Catalyzed by Amberlite IRA400-Cl Resin/I₂/KI via Multicomponent Reaction
  作者：Gurusamy Harichandran、Savarimuthu David Amalraj、Ponnusamy Shanmugam

  DOI：10.1002/jhet.1516

  日期：2013.5

  A facile and efficient one‐pot, solid supported synthesis of functionalized piperidine derivatives catalyzed by Amberlite IRA400‐Cl resin/I2/KI via a multicomponent reaction of various aldehydes, aromatic amines, and 1,3‐dicarbonyl compounds has been achieved. The reaction has been carried out in a one‐pot reaction and Amberlite resin as a solid supported catalyst at room temperature. Shorter reaction

  Amberlite IRA400-Cl树脂/ I 2 / KI通过各种醛，芳族胺和1,3-二羰基化合物的多组分反应，实现了简便，高效的单锅固相支持的官能化哌啶衍生物的合成。反应是在室温下以单锅反应和Amberlite树脂作为固体负载型催化剂进行的。较短的反应时间，简便的后处理，收率和温和的反应条件使这种新颖的合成策略既实用又有吸引力。
• Nanomagnetic organic–inorganic hybrid (Fe@Si-Gu-Prs): a novel magnetically green catalyst for the synthesis of tetrahydropyridine derivatives at room temperature under solvent-free conditions
  作者：Hossein Eshghi、Amir Khojastehnezhad、Farid Moeinpour、Shima Rezaeian、Mehdi Bakavoli、Mohsen Teymouri、Amin Rostami、Kamahldin Haghbeen

  DOI：10.1016/j.tet.2014.12.010

  日期：2015.1

  A novel nanomagnetic organic-inorganic hybrid catalyst (Fe@Si-Gu-Prs) was prepared by the chemical anchoring of Preyssler heteropolyacid (H-14[NaP5W30O110]) onto the surface of modified Fe3O4 magnetic nanoparticles with guanidine-propyl-trimethoxysilane linker. The synthesized magnetically green catalyst has been characterized with several methods (FTIR, SEM, TEM, EDS, VSM, TGA-DTG, XRD, BET, and ICP) and these techniques confirmed that the Preyssler heteropolyacid is well dispersed on the surface of the solid support and its structure is retained after immobilization on the modified silica-coated Fe3O4 nanoparticles, also the content of W in catalyst was measured by inductively coupled plasma optical emission spectroscopy (ICP-OES). After full characterization, its catalytic activity investigated in the synthesis of tetrahydropyridine derivatives at room temperature under solvent-free conditions. This nano hybrid catalyst can carry out the reactions in lower than 45 min with excellent yields, and the catalyst is easily isolated from the reaction mixture by an external magnet and reused at least five times without significant loss of activity. (C) 2014 Elsevier Ltd. All rights reserved.