methyl 1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-2,6-dip-tolyl-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: methyl 1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-2,6-dip-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 1,2,5,6-tetrahydro-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-2,6-bis(4-tolyl)pyridine-3-carboxylate；methyl 2,6-bis(4-methylphenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl (2S,6R)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-2,6-bis(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₅H₃₆N₂O₄
• 分子量: 548.682
• InChiKey: UNNOJENDCNIITC-UZNNEEJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  对甲基苯甲醛 、 甲氧苯胺 、 乙酰乙酸甲酯 在 ziconium(IV) oxychloride octahydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到methyl 1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-2,6-dip-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  通过ZrOCl 2 ·8H 2 O催化的芳香醛与胺和乙酰乙酸酯的串联反应有效地一锅法合成官能化的哌啶骨架

  摘要：

  通过与水相容的ZrOCl 2 ·8H 2 O催化剂，通过芳族醛，胺和乙酰乙酸酯的串联反应，开发了一种高效的非对映选择性一锅合成的官能化哌啶。

  DOI：

  10.1016/j.tetlet.2011.03.116

文献信息

• 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。
• Synthesis of Highly Functionalized Piperidines via One-Pot, Five-Component Reactions in the Presence of Acetic Acid Solvent
  作者：Mojtaba Lashkari、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani、Seyed Sajad Sajadikhah、Razieh Doostmohamadi

  DOI：10.1080/00397911.2011.601534

  日期：2013.1.1

  developed for one-pot, five-component synthesis of highly functionalized piperidines from reactions of β-keto esters, aromatic aldehydes, and various amines catalyzed in acetic acid medium. The reaction proceeded smoothly to generate the corresponding product in good yield. We have found that the use of acetic acid as reaction medium has a remarkable beneficial effect on the reaction, allowing it to

  摘要 开发了一种简单有效的方法，用于由 β-酮酯、芳香醛和各种胺在乙酸介质中的催化反应一锅法、五组分合成高度官能化的哌啶。反应进行得很顺利，以良好的收率生成相应的产物。我们发现使用乙酸作为反应介质对反应具有显着的有益影响，允许其在不需要加入催化剂的情况下进行，这是在其他类似报道的方法中的情况。在所有情况下，取代的哌啶从溶液中沉淀出来。图形概要
• Efficient, rapid avenue for synthesis of highly substituted piperidines using polystyrene sulfonic acid
  作者：Abhijeet Mulik、Pravin Hegade、Dayanand Patil、Ganpatrao Mulik、Suresh Salunkhe、Madhukar Deshmukh

  DOI：10.1007/s11164-016-2649-x

  日期：2017.2

  diasterioselective, multicomponent, one-pot synthesis of densely substituted piperidine derivatives has been elaborated using polystyrene sulfonic acid catalyst via tandem reactions of 1,3-dicarbonyl compounds, aromatic aldehydes and various amines. Shorter reaction times, high yields and a polymer-supported inexpensive catalyst are the noteworthy aspects of the scaffold. Graphical Abstract

  摘要 使用聚苯乙烯磺酸催化剂，通过1,3-二羰基化合物，芳族醛和各种胺的串联反应，精心设计了精心设计的非对映选择性，多组分，一锅法合成高取代度哌啶衍生物。较短的反应时间，高产率和聚合物负载的廉价催化剂是支架的值得注意的方面。 图形概要
• Nickel (II) Chloride Hexahydrate as an Efficient Catalyst for the Preparation of Highly Functionalised Piperidine Derivatives
  作者：Mohammad Reza Mohammad Shafiee、Batool Hojati Najafabadi、Majid Ghashang

  DOI：10.3184/174751912x13351985240633

  日期：2012.6

  Nickel (II) chloride hexahydrate (NiCl2.6H2O) has been employed for the efficient synthesis of highly functionalised piperidines via three-component cyclo-condensation reaction of aldehydes, aromatic amines and acetoacetic esters in ethanol under ambient condition. The key advantages of this procedure are high yields, easy work-up and purification of products by non-chromatographic methods.

  六水氯化镍 (II) (NiCl2.6H2O) 已用于在环境条件下通过醛、芳香胺和乙酰乙酸酯在乙醇中的三组分环缩合反应有效合成高度官能化的哌啶。该程序的主要优点是产量高、易于后处理和通过非色谱方法纯化产品。
• Y(NO₃)₃·4H₂O-assisted Three-component Synthesis of Polysubstituted Tetrahydropyridines
  作者：Mir Rasul Mousavi、Jasem Aboonajmi、Malek Taher Maghsoodlou、Nourallah Hazeri

  DOI：10.3184/174751914x13890195583234

  日期：2014.2

  A mild and efficient method for the synthesis of polysubstituted tetrahydropyridines has been developed which involves a three-component reaction of an arylamine (2 equiv.), an araldehyde (2 equiv.) and ethyl (or methyl) acetoacetate (1 equiv.) in MeCN under ambient conditions, in the presence of yttrium nitrate, Y(NO₃)₃·4H₂O. This appears to be the first time yttrium nitrate has been used as a catalyst for this type of synthesis of tetrahydropyridines.

  在硝酸钇（Y(NO3)3-4H2O）存在的条件下，在 MeCN 中进行芳胺（2 等份）、芳醛（2 等份）和乙酰乙酸乙酯（或乙酰乙酸甲酯）（1 等份）的三组分反应。这似乎是首次使用硝酸钇作为催化剂合成四氢吡啶类化合物。