ethyl 2,6-diphenyl-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1413946-25-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 2,6-diphenyl-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl 4-(4-tolylamino)-1,2,5,6-tetrahydro-2,6-diphenyl-1-(4-tolyl)pyridine-3-carboxylate；Ethyl 2,6-diphenyl-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 4-(4-methylanilino)-1-(4-methylphenyl)-2,6-diphenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1413946-25-4
• 化学式: C₃₄H₃₄N₂O₂
• 分子量: 502.656
• InChiKey: KOYOWUYGCUEITP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  苯甲醛 、 乙烷,三氯氟- 、 乙酰乙酸甲酯 在 bismuth(III) nitrate 作用下， 以 乙醇 为溶剂， 反应 0.42h， 以78%的产率得到ethyl 2,6-diphenyl-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Multicomponent synthesis and antimicrobial activity of alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3-carboxylates

  摘要：

  Reaction of arylamines with aromatic aldehydes and beta-ketoesters in the presence of bismuth nitrate or crystalline iodine as a catalyst afforded to alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3-carboxy-lates. Antimicrobial activity of the obtained compounds was studied.

  DOI：

  10.1134/s1070363215040131

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。
• Synthesis of Highly Functionalized Piperidines Using Polyphosphoric Acid Supported on Silica-coated Magnetic Nanoparticles
  作者：Amir Khojastehnezhad、Behrooz Maleki、Behnaz Karrabi、Esmail Rezaei Seresht

  DOI：10.1080/00304948.2017.1342505

  日期：2017.7.4

  Moreover, some of themhavebeenfoundtobeusefulasinhibitorsofaminopeptidaseandalpha-glucosidase. Numerous recent methods reported for the synthesis of highly substituted piperidines use various catalytic systems such as bismuth nitrate, molecular iodine, bromodimethyl-sulfonium bromide (BDMS), tetra(n-butyl)ammonium tribromide (TBATB), InCl3, 21 CAN, ZrOCl2.8H2O, 23 picric acid, ionic liquids, ZrCl4, 26

  磁性纳米粒子在催化领域的应用已成为一个有用的研究领域。功能化磁性纳米粒子 (MNPs) 已被用于有机合成，在氧化、氢化、C-C 偶联、烯烃的二羟基化和胺化反应中显示出优异的催化活性。目前，很多注意力都集中在通过在其周围涂覆二氧化硅壳来合成磁性核壳结构。MNPs 是一种高效、容易获得的多相催化剂，具有出色的稳定性。大多数负载型催化剂通过过滤或离心分离，这可能导致催化剂的损失。为了克服这种可能的复杂性，MNP 已成为有效的支持物，因为它们可以通过外部永磁体与反应混合物分离。功能化哌啶及其衍生物是一类非常重要的杂环化合物，因为它们具有多种生物活性。许多带有这种杂环单元的化合物已显示出多种有趣的生物活性，如抗炎、抗氧化、抗菌、抗疟疾和抗结核特性。此外，已发现其中一些可用作氨基肽酶和α-葡萄糖苷酶的抑制剂。最近报道的许多合成高取代哌啶的方法使用各种催化系统，如硝酸铋、分子碘、溴化二甲基溴化锍 (BDMS)、四（正丁基）三溴化铵
• Multicomponent preparation of highly functionalized piperidines using magnesium hydrogen sulfate as an efficient catalyst
  作者：Mohammad Reza Mohammad Shafiee、Batool Hojati Najafabadi、Majid Ghashang

  DOI：10.1007/s11164-012-0878-1

  日期：2013.10

  Abstract A simple, highly versatile, and efficient synthesis of functionalized piperidines is achieved by four-component cyclo-condensation of aldehydes, aromatic amines, and acetoacetic esters using magnesium hydrogen sulfate [Mg(HSO4)2] as a catalyst in acetonitrile as the solvent at room temperature. The key advantages of this procedure are high yields, easy work-up, and purification of products

  摘要 以硫酸氢镁[Mg（HSO 4）2 ]为催化剂，通过乙醛，芳族胺和乙酰乙酸酯的四组分环缩合反应，可以简单，高效地合成官能化哌啶。在室温下的溶剂。该方法的主要优点是高产率，易于后处理和通过非色谱法纯化产物。 图形概要
• 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。
• Alum as an efficient catalyst for the multicomponent synthesis of functionalized piperidines
  作者：Ramneet Kaur、Annah Gupta、Kamal K. Kapoor

  DOI：10.1007/s11164-017-2979-3

  日期：2017.11

  An effective approach to the synthesis of functionalized piperidines via a one-pot multicomponent reaction of aniline, β-ketoester and aldehyde in the presence of alum as an efficient catalyst has been reported. The present procedure offers advantages such as simple workup, short reaction time and offers rapid access to a variety of functionalized piperidines.

  已经报道了在明矾作为有效催化剂的存在下通过苯胺，β-酮酸酯和醛的一锅多组分反应合成官能化哌啶的有效方法。本方法提供了诸如后处理简单，反应时间短的优点，并且提供了快速获得各种官能化哌啶的优点。