ethyl 4-(4-tolylamino)-1,2,5,6-tetrahydro-1,2,6-tri(p-tolyl)pyridine-3-carboxylate | 1413946-22-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 4-(4-tolylamino)-1,2,5,6-tetrahydro-1,2,6-tri(p-tolyl)pyridine-3-carboxylate
• 英文别名: ethyl 1,2,6-tri-p-tolyl-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 2,6-bis-(4-methylphenyl)-1-(4-methylphenyl)-4-(4-methylphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；Ethyl 4-(p-tolylamino)-1,2,5,6-tetrahydro-1,2,6-tri-p-tolylpyridine-3-carboxylate；ethyl 4-(4-methylanilino)-1,2,6-tris(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1413946-22-1
• 化学式: C₃₆H₃₈N₂O₂
• 分子量: 530.71
• InChiKey: CEUZECMTKANHCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 乙酰乙酸乙酯 、 乙烷,三氯氟- 在 1,3-disulfonic acid benzimidazolium chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.8h， 以86%的产率得到ethyl 4-(4-tolylamino)-1,2,5,6-tetrahydro-1,2,6-tri(p-tolyl)pyridine-3-carboxylate
  参考文献：
  名称：

  一种新型离子液体1,3-二磺酸苯并咪唑鎓氯化物的设计，制备和表征，它是在无溶剂条件下合成四氢吡啶的有效且可回收的催化剂†

  摘要：

  在目前的工作中，合成了作为新型离子液体的1,3-二磺酸苯并咪唑鎓盐，并对其FT-IR，1 H NMR，13 C NMR以及质谱进行了表征。该离子液体用作高效，均质和可回收的催化剂，可通过以下途径合成高度官能化的四氢吡啶在无溶剂条件下，单锅多组分缩合芳族醛，乙酰乙酸乙酯和苯胺。当前的合成路线是一种绿色方案，具有几个优点，例如产品收率高，反应时间短，反应条件温和，化学废物最少，后处理程序容易。此外，该催化剂可以重复使用和回收至少四次而没有明显的活性损失。

  DOI：

  10.1039/c5ra10699k

文献信息

• Diastereoselective Synthesis of Symmetrical and Unsymmetrical Tetrahydropyridines Catalyzed by Bi(III) Immobilized on Triazine Dendrimer Stabilized Magnetic Nanoparticles
  作者：Beheshteh Asadi、Amir Landarani-Isfahani、Iraj Mohammadpoor-Baltork、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani、Hadi Amiri Rudbari

  DOI：10.1021/acscombsci.6b00180

  日期：2017.6.12

  the first time from a five-component Fe3O4@TDSN-Bi(III)-catalyzed reaction of aryl aldehydes, aryl amines, and ethyl acetoacetate. This magnetically separable catalyst enabled the selective incorporation of two different aryl amines or two different aryl aldehydes into the product, and provided excellent yields, short reaction times, mild reaction conditions, satisfactory catalyst recyclability, and

  首次从五组分Fe 3 O 4 TDSN-Bi（III）催化的芳基醛，芳基胺和乙酰乙酸乙酯的反应中获得不对称的1,2,5,6-四氢吡啶-3-羧酸酯。该磁性可分离的催化剂能够将两种不同的芳基胺或两种不同的芳基醛选择性地掺入产物中，并提供优异的收率，较短的反应时间，温和的反应条件，令人满意的催化剂可回收性和较低的催化剂负载量。
• Nano-Mn-[4-Benzyloxyphenyl-salicylaldimine-methylpyranopyrazole-carbonitrile]Cl₂ as a New Schiff Base Complex and Catalyst for the Synthesis of Highly Substituted Tetrahydropyridines
  作者：Ahmad Reza Moosavi-Zare、Hamid Goudarziafshar、Majid Asgari Delkhosh、Zahra Jalilian

  DOI：10.1080/00304948.2021.1920302

  日期：2021.7.4

  (2021). Nano-Mn-[4-Benzyloxyphenyl-salicylaldimine-methylpyranopyrazole-carbonitrile]Cl2 as a New Schiff Base Complex and Catalyst for the Synthesis of Highly Substituted Tetrahydropyridines. Organic Preparations and Procedures International: Vol. 53, No. 4, pp. 402-412.

  (2021)。Nano-Mn-[4-Benzyloxyphenyl-salicylaldimine-methylpyranopyrazole-carbonitrile]Cl2 作为一种新型席夫碱配合物和催化剂用于合成高度取代的四氢吡啶。国际有机制剂和程序：卷。53，第 4 期，第 402-412 页。
• Multi-component synthesis of piperidines and dihydropyrrol-2-one derivatives catalyzed by a dual-functional ionic liquid
  作者：Narjes Basirat、Seyed Sajad Sajadikhah、Abdolkarim Zare

  DOI：10.1177/1747519819883881

  日期：2020.1

  ([TMBSED][OMs]2) was employed for the synthesis of piperidines and dihydropyrrol-2-ones via one-pot multi-component reactions in simple and green processes. This pseudo five-component reaction of aromatic aldehydes, anilines and alkyl acetoacetates was carried out under reflux conditions in ethanol to afford substituted piperidines. Also, dihydropyrrol-2-one derivatives were synthesized by means of four-component

  N,N,N',N'-四甲基-N,N'-双(磺基)乙烷-1,2-甲磺酸二胺 ([TMBSED][OMs]2) 用于合成哌啶和二氢吡咯-2-在简单和绿色的过程中通过一锅多组分反应进行生产。这种芳香醛、苯胺和乙酰乙酸烷基酯的假五组分反应在回流条件下在乙醇中进行，得到取代的哌啶。此外，二氢吡咯-2-one 衍生物通过各种胺、乙炔二羧酸二烷基酯和甲醛在室温下在乙醇中的四组分反应合成。目前的方法有几个优点，如产率高、后处理容易、反应时间短，以及利用温和和清洁的反应条件。
• Fe(NO₃)₃·9H₂O as Efficient Catalyst for One-pot Synthesis of Highly Functionalized Piperidines
  作者：Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Jasem Aboonajmi、Seyed Sajad Sajadikhah

  DOI：10.1002/jccs.201200421

  日期：2013.4

  Fe(NO3)3·9H2O is used as an efficient and effective catalyst for the one‐pot three‐component synthesis of highly functionalized piperidines from aromatic aldehydes, anilines and b–ketoesters in ethanol at ambient temperature. This procedure includes some important aspects like the easy work‐up, no need to column chromatography, simple and readily available precursors, and good to high yields.

  Fe（NO 3）3 ·9H 2 O可作为一种有效的催化剂，用于在环境温度下由芳族醛，苯胺和b-酮酸酯在乙醇中一锅三组分合成高度官能化的哌啶。该程序包括一些重要方面，例如易于处理，无需柱色谱，简单易用的前体以及良好到高收率。
• Synthesis, characterization and first application of keggin-type heteropoly acids supported on silica coated NiFe₂O₄as novel magnetically catalysts for the synthesis of tetrahydropyridines
  作者：Hossein Eshghi、Amir Khojastehnezhad、Farid Moeinpour、Mehdi Bakavoli、Seyed Mohammad Seyedi、Mohsen Abbasi

  DOI：10.1039/c4ra05133e

  日期：——

  In this study, two heteroploly acids with Keggin structures (phosphotungestic acid (PWA) and phosphomolybdic acid (PMA)) have been supported on silica coated nickel ferrite nanoparticles (NiFe2O4@SiO2). The synthesized catalysts were characterized by several methods (FT-IR, SEM, TEM, VSM, XRD, BET and ICP-AES), and the catalytic activities of these new and magnetic catalysts in synthesis of tetrahydropyridine derivatives have been investigated. These new catalysts showed that they can carry out reactions at room temperature in a short time and under solvent-free conditions. Moreover, the obtained results indicated that PWA supported NiFe2O4@SiO2 is a stronger acid than PMA to run these reactions. More importantly, the catalysts were easily isolated from the reaction mixture by a magnetic bar and reused at least five times without significant degradation in their activities.

  在这项研究中，采用Keggin结构的两种异源多酸（磷钨酸（PWA）和磷钼酸（PMA））被负载在涂有二氧化硅的镍铁氧体纳米颗粒（NiFe2O4@SiO2）上。合成的催化剂采用多种方法进行表征（FT-IR、SEM、TEM、VSM、XRD、BET和ICP-AES），并研究了这些新型磁性催化剂在合成四氢吡啶衍生物中的催化活性。这些新催化剂表明，它们能够在室温下、短时间内及无溶剂条件下进行反应。此外，获得的结果表明，负载PWA的NiFe2O4@SiO2在进行这些反应时比PMA具有更强的酸性。更重要的是，催化剂可以通过磁棒轻松从反应混合物中分离出来，并在未显著降低活性的情况下重复使用至少五次。