ethyl (2RS,6SR)-2,6-bis(4-chlorophenyl)-1-(4-methylphenyl)-4-(4-methylphenylamino)-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 (2RS,6SR)-2,6-bis(4-chlorophenyl)-1-(4-methylphenyl)-4-(4-methylphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl 4-(p-tolylamino)-2,6-bis(4-chlorophenyl)-1,2,5,6-tetrahydro-1-p-tolylpyridine-3-carboxylate；PRK117；2,6-bis-(4-chlorophenyl)-1-p-tolyl-4-p-tolylamino-1,2,5,6-tetrahydropyridine-3-carboxylic acid ethyl ester；ethyl 2,6-bis(4-chlorophenyl)-1-(4-methylphenyl)-4-(4-methylphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl (2S,6R)-2,6-bis(4-chlorophenyl)-4-(4-methylanilino)-1-(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₄H₃₂Cl₂N₂O₂
• 分子量: 571.546
• InChiKey: YGFNKCHRZYXYFR-CQTOTRCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  乙酰乙酸乙酯 、 4-氯苯甲醛 、 乙烷,三氯氟- 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88%的产率得到ethyl (2RS,6SR)-2,6-bis(4-chlorophenyl)-1-(4-methylphenyl)-4-(4-methylphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  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

• 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。
• One-Pot Three-Component Synthesis of Highly Substituted Piperidines Using 1-Methyl-2-Oxopyrrolidinium Hydrogen Sulfate
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Adel Beigbabaei、Mojtaba Lashkari

  DOI：10.3184/174751912x13395258340271

  日期：2012.8

  1-Methyl-2-oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO4]) is used as an ionic liquid catalyst for the one-pot three-component synthesis of highly substituted piperidines from aromatic aldehydes, anilines and β–ketoesters in refluxing ethanol. This homogeneous catalyst procedure has the advantages of easy work-up, no need for column chromatography, simple and readily available precursors, and good

  1-甲基-2-氧代吡咯烷硫酸氢盐 ([Hpyro][HSO4]) 用作离子液体催化剂，用于在回流乙醇中由芳香醛、苯胺和 β-酮酯一锅三组分合成高度取代的哌啶。这种均相催化剂程序具有后处理简单、无需柱色谱、前体简单易得、收率高的优点。
• 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。
• Metal-Free, One-Pot, Rapid Synthesis of Tetrahydropyridines Using Acetic Acid as Solvent and Catalyst at Room Temperature
  作者：Umamahesh Balijapalli、Sathishkumar Munusamy、Karthikeyan Natesan Sundaramoorthy、Sathiyanarayanan Kulathu Iyer

  DOI：10.1080/00397911.2013.838266

  日期：2014.4.3

  alternative approach for not only highly substituted tetrahydropyridines (THPs) but also fully substituted tetrahydropyridines (FTHPs) in moderate to good yields. The plausible mechanism for the formation of THPs was greatly promoted by the H+ ion coming from acetic acid. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following

  摘要 在无金属催化剂的条件下，通过串联反应开发了乙酸促进的四氢吡啶一锅法合成。该协议的一些重要特点是原子经济性高、收率好、程序简单、无需昂贵的柱层析、反应时间更短、无金属和反应条件温和。目前的方法不仅为高度取代的四氢吡啶 (THP) 和完全取代的四氢吡啶 (FTHP) 提供了一种替代方法，收率中等至良好。来自乙酸的 H+ 离子极大地促进了 THP 形成的合理机制。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版本，获取以下免费补充资源：
• A Facile and Efficient Solid Supported, One-Pot Synthesis of Functionalized Piperidine Derivatives Catalyzed by Amberlite IRA400-Cl Resin/I₂/KI via Multicomponent Reaction
  作者：Gurusamy Harichandran、Savarimuthu David Amalraj、Ponnusamy Shanmugam

  DOI：10.1002/jhet.1516

  日期：2013.5

  A facile and efficient one‐pot, solid supported synthesis of functionalized piperidine derivatives catalyzed by Amberlite IRA400‐Cl resin/I2/KI via a multicomponent reaction of various aldehydes, aromatic amines, and 1,3‐dicarbonyl compounds has been achieved. The reaction has been carried out in a one‐pot reaction and Amberlite resin as a solid supported catalyst at room temperature. Shorter reaction

  Amberlite IRA400-Cl树脂/ I 2 / KI通过各种醛，芳族胺和1,3-二羰基化合物的多组分反应，实现了简便，高效的单锅固相支持的官能化哌啶衍生物的合成。反应是在室温下以单锅反应和Amberlite树脂作为固体负载型催化剂进行的。较短的反应时间，简便的后处理，收率和温和的反应条件使这种新颖的合成策略既实用又有吸引力。