1-phenyl-4-phenylamino-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-phenyl-4-phenylamino-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-phenyl-4-(phenylamino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 1,2,5,6-tetrahydro-1-phenyl-4-(phenylamino)-2,6-di(p-tolyl)pyridine-3-carboxylate；ethyl (2S,6R)-4-anilino-2,6-bis(4-methylphenyl)-1-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₄H₃₄N₂O₂
• 分子量: 502.656
• InChiKey: NBVXLYNBQKTYAQ-CQTOTRCISA-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：

  对甲基苯甲醛 、 乙酰乙酸乙酯 、 苯胺 在 ferric hydrogen sulfate-supported silica-coated magnetic nanoparticles 作用下， 以 乙醇 、 乙醇-D1 为溶剂， 反应 4.75h， 以89%的产率得到1-phenyl-4-phenylamino-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Nanomagnetically modified ferric hydrogen sulfate (NiFe2O4@SiO2-FHS): a reusable green catalyst for the synthesis of highly functionalized piperidine derivatives

  摘要：

  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。

  DOI：

  10.1007/s13738-014-0546-z

文献信息

• Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds
  作者：Sanny Verma、Subodh Kumar、Suman L. Jain、Bir Sain

  DOI：10.1039/c1ob05818e

  日期：——

  The utility of thiourea dioxide as an efficient organocatalyst for the library synthesis of novel heterocyclic compoundsvia one-pot multicomponent coupling reactions is disclosed. Thiourea dioxide is an inexpensive and readily accessible catalyst, resulting in better product yields as compared to the corresponding thiourea as catalyst. Thiourea dioxide is found to be insoluble in various organic solvents and therefore at the end of the reaction products can be separated by extraction with diethyl ether and the recovered catalyst can be used several times with consistent catalytic activity.

  介绍了二氧化硫脲作为高效有机催化剂在一锅多组分偶联反应中合成新型杂环化合物的应用。与相应的硫脲催化剂相比，二氧化硫脲作为一种廉价且易于获得的催化剂，能带来更好的产物收率。二氧化硫脲在多种有机溶剂中难以溶解，因此反应结束后，产物可通过乙醚萃取分离，且回收的催化剂能多次重复使用，保持稳定的催化活性。
• Application and developing of iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) as an efficient and reusable heterogeneous nanocatalyst in the synthesis of heterocyclic compounds
  作者：Hashem Sharghi、Jasem Aboonajmi、Mozhdeh Mozaffari、Mohammad Mahdi Doroodmand、Mahdi Aberi

  DOI：10.1002/aoc.4124

  日期：2018.3

  Iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs) is an efficient, ecofriendly and reusable heterogeneous nanocatalyst for the one‐pot synthesis of heterocyclic compounds including bis‐spiro piperidines, piperidines, dihydro‐2‐oxopyrroles, pyrazoles and diazepines at room temperature with good to excellent yields. The heterogeneous nanocatalyst was fully characterized by scanning electron microscopy

  铁掺杂的多壁碳纳米管（Fe / MWCNTs）是一种高效，生态友好且可重复使用的多相纳米催化剂，用于在室温下单锅合成杂环化合物，包括双螺哌啶，哌啶，二氢-2-氧吡咯，吡唑和二氮杂s温度高到极好的产量。通过扫描电子显微镜（SEM），X射线衍射（XRD），电感耦合等离子体（ICP）和FT-IR分析充分表征了多相纳米催化剂。同样，所有制备的化合物的结构均通过1 H NMR表征，13C NMR，FT-IR，质谱（MS）和元素分析。这些规程的主要优点是温和且绿色的反应条件，较短的反应时间，清洁的反应，操作简单，易于纯化以及可重复使用的多相纳米催化剂的产率高至优异。将该催化剂循环十次而活性没有明显损失。
• Highly efficient one-pot synthesis of tetrahydropyridines
  作者：Ghorbani-Vaghei Ramin、Shahbazi Hajar

  DOI：10.1016/j.crci.2013.02.015

  日期：2013.11

  Résumé The combination of aromatic aldehydes, and 1,3-dicarbonyl compounds in the presence of a catalytic amount of poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA] leads to the formation of highly substituted tetrahydropyridines. In this way, a series of pharmacologically interesting substituted piperidine derivatives were obtained in moderate to high yields at room temperature. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  简历 在聚(N,N'-二溴-N-乙基-苯-1,3-二磺酰胺)[PBBS]和N,N,N',N'-四溴苯-1,3-二磺酰胺[TBBDA]的催化量存在下，芳香醛与1,3-二羰基化合物的组合导致高度取代的四氢吡啶的形成。通过这种方式，在室温下以中等至高收率获得了一系列具有药理学意义的取代哌啶衍生物。 补充材料： 本文的补充材料以单独文件形式提供： mmc1.docx
• Multicomponent reaction for the synthesis of highly functionalized piperidine scaffolds catalyzed by TMSI
  作者：Lisha Wu、Shiqiang Yan、Wensheng Wang、Yinta Li

  DOI：10.1007/s11164-020-04208-6

  日期：2020.9

  An efficient method for the synthesis of highly functionalized piperidines via one-pot domino reaction of β-ketoesters, aromatic aldehydes, and aromatic amines was reported. This multicomponent coupling was catalyzed by TMSI in methanol at room temperature, giving desired substituted pyridines in moderate to good yields.

  报道了一种通过β-酮酸酯，芳族醛和芳族胺的一锅多米诺反应合成高官能化哌啶的有效方法。室温下在甲醇中，TMSI催化这种多组分偶联，得到所需的取代吡啶。
• Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature
  作者：Goutam Brahmachari、Suvankar Das

  DOI：10.1016/j.tetlet.2012.01.042

  日期：2012.3

  diastereoselective multicomponent one-pot synthesis of a series of pharmaceutically interesting functionalized piperidine derivatives has been developed based on a low-cost and environmentally benign Bi(NO3)3·5H2O catalyst via tandem reactions of 1,3-dicarbonyl compounds, aromatic aldehydes, and various amines in ethanol at room temperature. High atom-economy, good yields, eco-friendliness, and mild reaction conditions

  基于低成本和环境友好的Bi（NO 3）3 ·5H 2 O催化剂，通过串联反应进行了简单，直接和高效的非对映选择性多组分一锅合成一系列可药用的功能化哌啶衍生物。室温下在乙醇中的1,3-二羰基化合物，芳族醛和各种胺。高原子经济性，良好的产率，生态友好性和温和的反应条件是该方案的一些重要特征。