ethyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-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: ethyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: PRK112；ethyl 1,2,5,6-tetrahydro-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-2,6-bis(4-tolyl)pyridine-3-carboxylate；ethyl (2S,6R)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-2,6-bis(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₆H₃₈N₂O₄
• 分子量: 562.709
• InChiKey: OGFMGNOQSFFHKP-QWOOXDRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 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 、 乙酰乙酸乙酯 、 甲氧苯胺 在 cerium(IV) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以90%的产率得到ethyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Cerium(IV) triflate-catalyzed domino annulation approaches to the synthesis of highly substituted piperidines

  摘要：

  简述了以三(IV)铈为催化剂，通过缩合β-酮酯、芳香醛和苯胺合成高官能度哌啶的一条简单、非对映选择性、廉价且高效的路线。在大多数情况下，哌啶会从溶液中析出。

  DOI：

  10.1016/j.crci.2013.03.011

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。
• 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。
• 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。
• Tartaric acid: a natural, green and highly efficient catalyst for the one-pot synthesis of functionalized piperidines
  作者：Jasem Aboonajmi、Malek Taher Maghsoodlou、Nourallah Hazeri、Mojtaba Lashkari、Mehrnoosh Kangani

  DOI：10.1007/s11164-014-1877-1

  日期：2015.11

  Abstract Tartaric acid is a highly effective and efficient catalyst for the one-pot synthesis of highly substituted piperidines through a combination of 1,3-dicarbonyl compounds, aromatic aldehydes, and various amines in methanol at room temperature. The advantages of this protocol are good yields, short reaction time, mild reaction conditions, no need for column chromatography, easy access, simple

  摘要 酒石酸是一种高效和高效的催化剂，用于在室温下通过甲醇中1,3-二羰基化合物，芳族醛和各种胺的组合一锅合成高取代的哌啶。该方案的优点是收率高，反应时间短，反应条件温和，无需柱色谱法，操作简便，后处理步骤简单，催化剂便宜且可生物降解。 图形概要