methyl 2,6-bis(phenyl)-1-(4-fluorophenyl)-4-(4-fluorophenylamino)-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 2,6-bis(phenyl)-1-(4-fluorophenyl)-4-(4-fluorophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl (2S,6R)-4-(4-fluoroanilino)-1-(4-fluorophenyl)-2,6-diphenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₁H₂₆F₂N₂O₂
• 分子量: 496.556
• InChiKey: AHRBLFBAYDOJQR-MFMCTBQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  37
• 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：

  苯甲醛 、 乙酰乙酸甲酯 、 4-氟苯胺 在 碘化锑 作用下， 以 乙醇 为溶剂， 反应 5.83h， 以78%的产率得到methyl 2,6-bis(phenyl)-1-(4-fluorophenyl)-4-(4-fluorophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  引入三碘化锑（SbI 3）作为合成多官能哌啶的新型高效催化剂

  摘要：

  摘要本文 报道了在催化量存在下通过芳香醛，苯胺和 β- 酮酯的串联缩合反应合成高度多样化的哌啶的高效简便的单锅多组分反应方法 （15在50°C下在EtOH中的SbI 3（mol％）。该方案的优点是易于加工且廉价，催化剂和溶剂易于获得，并且产生了良好的产率。 图形概要

  DOI：

  10.1007/s11164-016-2582-z

文献信息

• Citric acid, a green catalyst for the one-pot, multi-component synthesis of highly substituted piperidines
  作者：Zahra Madanifar、Malek-Taher Maghsoodlou、Mehrnoosh Kangani、Nourallah Hazeri

  DOI：10.1007/s11164-015-1993-6

  日期：2015.12

  Citric acid has been used as a green and efficient catalyst for one-pot, multi-component synthesis of highly substituted piperidines by condensation of aromatic aldehydes, aromatic amines, and β-ketoesters in MeOH at ambient temperature. This method has several advantages including use of a nonhazardous and inexpensive catalyst, easy work-up, clean reaction conditions, and high yields.

  柠檬酸已被用作绿色高效的催化剂，用于在环境温度下通过在甲醇中的芳香醛，芳香胺和β-酮酸酯的缩合反应一锅多组分合成高度取代的哌啶。该方法具有几个优点，包括使用无害且廉价的催化剂，易于后处理，干净的反应条件和高收率。
• Cerium(IV) triflate-catalyzed domino annulation approaches to the synthesis of highly substituted piperidines
  作者：Samad Khaksar、Seyed Mohammad Vahdat、Mandana Alipour

  DOI：10.1016/j.crci.2013.03.011

  日期：2013.11

  Résumé A simple, diastereoselective, inexpensive, and efficient route for the synthesis of highly functionalized piperidines by the condensation of β-keto-esters, aromatic aldehydes and anilines using cerium(IV) triflate as a catalyst is described. In most cases, the piperidine precipitates out of the solution.

  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。
• H<sub>3</sub>PW<sub>12</sub>O<sub>40</sub>-Catalyzed Multicomponent Reaction for Efficient Synthesis of Highly Substituted Piperidines
  作者：Samad Khaksar、Seyed Baghbanian、Nastaran Barsan

  DOI：10.2174/1386207316666131229132950

  日期：2013.12.29

  A simple, diastereoselective, inexpensive, and efficient route for the synthesis of highly functionalized piperidines by the condensation of β-keto-esters, aromatic aldehydes and anilines using H3PW12O40 as a catalyst is described. The catalyst could be easily recovered after completion of the reaction and reused without a considerable change in its activity. Furthermore, in most cases the piperidine precipitates out of solution.

  以 H3PW12O40 为催化剂，通过 β 酮酯、芳香醛和苯胺的缩合合成高官能度哌啶的简单、非对映选择性、廉价和高效的路线被描述出来。反应完成后，催化剂可以很容易地回收并重复使用，而其活性不会发生很大变化。此外，在大多数情况下，哌啶会从溶液中析出。
• In vitro evaluation and in silico screening of synthetic acetylcholinesterase inhibitors bearing functionalized piperidine pharmacophores
  作者：Goutam Brahmachari、CheeYan Choo、Pravin Ambure、Kunal Roy

  DOI：10.1016/j.bmc.2015.06.005

  日期：2015.8

  A series of densely functionalized piperidine (FP) scaffolds was synthesized following a diastereoselective one-pot multicomponent protocol under eco-friendly conditions. The FPs were evaluated in vitro for their acetylcholinesterase (AChE) inhibitory activity, and in silico studies for all the target compounds were carried out using pharmacophore mapping, molecular docking and quantitative structure-activity relationship (QSAR) analysis in order to understand the structural features required for interaction with the AChE enzyme and the key active site residues involved in the intermolecular interactions. Halogenation, nitration or 3,4-methylenedixoxy-substitution at the phenyl ring attached to the 2- and 6-positions of 1,2,5,6-tetrahydropyridine nucleus in compounds 14-17, 19, 20, 24 and 26 greatly enhanced the AChE inhibitory activity. The docking analysis demonstrated that the inhibitors are well-fitted in the active sites. The in silico studies enlighten the future course of studies in modifying the scaffolds for better therapeutic efficacy against the deadly Alzheimer's disease. (C) 2015 Elsevier Ltd. All rights reserved.
• Introduction of antimony triiodide (SbI3) as a new and efficient catalyst for synthesis of polyfunctionalized piperidines
  作者：Farhad Omarzehi Chahkamali、Mohammad Reza Faghihi、Malek Taher Maghsoodlou

  DOI：10.1007/s11164-016-2582-z

  日期：2016.12

  Abstract In the present work, an efficient and convenient one-pot multi-component reaction is reported for the synthesis of highly diversified piperidines by tandem condensation reaction of aromatic aldehydes, anilines, and β -keto esters in the presence of a catalytic amount (15 mol%) of SbI3 in EtOH at 50 °C. The advantages of this protocol are that it is easy to work up and inexpensive, the catalyst

  摘要本文 报道了在催化量存在下通过芳香醛，苯胺和 β- 酮酯的串联缩合反应合成高度多样化的哌啶的高效简便的单锅多组分反应方法 （15在50°C下在EtOH中的SbI 3（mol％）。该方案的优点是易于加工且廉价，催化剂和溶剂易于获得，并且产生了良好的产率。 图形概要