methyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-68-4

• 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-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 1-(4-chlorophenyl)-4-(4-chlorophenylamino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate；Methyl 2,6-bis(4-fluorophenyl)-1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 4-(4-chloroanilino)-1-(4-chlorophenyl)-2,6-bis(4-fluorophenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-68-4
• 化学式: C₃₁H₂₄Cl₂F₂N₂O₂
• 分子量: 565.447
• InChiKey: NKNFICSDYLYWRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 对氯苯胺 、 乙酰乙酸甲酯 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以75%的产率得到methyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  硝酸铈铵催化的多组分反应有效合成功能化四氢吡啶

  摘要：

  据报道，在催化量的硝酸铈铵（CAN）存在下，β-酮酸酯，两当量的芳族醛和两当量的胺的多组分缩合反应可实现原子经济的一锅法合成功能化四氢吡啶。 。以这种方式，在室温下以中等至良好的产率获得了一系列药理学上有趣的取代的哌啶衍生物。

  DOI：

  10.1021/co100055x

文献信息

• One-pot five-component synthesis of highly functionalized piperidines using oxalic acid dihydrate as a homogenous catalyst
  作者：Seyed Sajad Sajadikhah、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani、Anthony C. Willis

  DOI：10.1016/j.cclet.2012.03.008

  日期：2012.5

  An efficient green protocol is described for the preparation of highly functionalized piperidines via a one-pot five-component reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of oxalic acid dihydrate as catalyst in ethanol at ambient temperature. The structure as well as the relative stereochemistry of these compounds was confirmed by single X-ray crystallographic analysis

  描述了一种有效的绿色方案，用于在乙二酸二水合物作为催化剂在乙醇中，环境温度下，通过芳族醛，苯胺和β-酮酸酯之间的一锅五组分反应制备高官能化的哌啶。这些化合物的结构和相对立体化学通过单X射线晶体学分析证实。
• 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
• An efficient one-pot multi-component synthesis of highly functionalized piperidines
  作者：Santosh V. Goswami、Prashant B. Thorat、Sudhakar R. Bhusare

  DOI：10.1515/hc-2012-0105

  日期：2012.12.1

  Abstract A simple, inexpensive and efficient one-pot synthesis of piperidine derivatives was achieved in excellent yield via the three-component reaction of substituted aniline, 1,3-dicarbonyl compound and aromatic aldehyde using phenylboronic acid as catalyst.

  摘要 以苯基硼酸为催化剂，通过取代苯胺、1,3-二羰基化合物和芳香醛的三组分反应，以优异的收率实现了简单、廉价、高效的哌啶衍生物一锅法合成。
• 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。
• LaCl3·7H2O as an Efficient Catalyst for One-Pot Synthesis of Highly Functionalized Piperidines via Multi-component Organic Reactions
  作者：Balijapalli Umamahesh、Venkatesan Sathesh、Gunasekar Ramachandran、Munusamy Sathishkumar、Kulatu Sathiyanarayanan

  DOI：10.1007/s10562-012-0829-x

  日期：2012.7

  The three-component one-pot synthesis of highly functionalized piperidine derivatives was carried out by condensing 1,3-dicarbonyl compounds with aromatic aldehydes and aniline using a catalytic amount (10 mol%) of LaCl3·7H2O in methanol at room temperature. The main features of current protocol include easy work up, mild reaction conditions, good yields and high atom economy.Graphical Abstract

  在室温下，使用催化量（10 mol%）的 LaCl3·7H2O 在甲醇中将 1,3-二羰基化合物与芳香醛和苯胺缩合，进行三组分一锅法合成高度官能化的哌啶衍生物。当前方案的主要特点包括易于操作、反应条件温和、产率高和原子经济性高。图形摘要