ethyl 1-(4-fluorophenyl)-4-(4-fluorophenylamino)-1,2,5,6-tetrahydro-2,6-bis(4-methylphenyl)pyridine-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-fluorophenyl)-4-(4-fluorophenylamino)-1,2,5,6-tetrahydro-2,6-bis(4-methylphenyl)pyridine-3-carboxylate
• 英文别名: ethyl 4-(4-fluoroanilino)-1-(4-fluorophenyl)-2,6-bis(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₄H₃₂F₂N₂O₂
• 分子量: 538.637
• InChiKey: OPAVGDAWODKKEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 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：
  6

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 乙酰乙酸乙酯 、 4-氟苯胺 在 ethylenediammonium diformate 作用下， 以 乙醇 为溶剂， 反应 6.5h， 以87%的产率得到ethyl 1-(4-fluorophenyl)-4-(4-fluorophenylamino)-1,2,5,6-tetrahydro-2,6-bis(4-methylphenyl)pyridine-3-carboxylate
  参考文献：
  名称：

  使用二甲酸乙二铵（EDDF）作为可重复使用的催化剂，绿色简便地合成二氢吡咯-2-酮和高度取代的哌啶

  摘要：

  摘要 对于二氢吡咯-2-酮和高度取代的哌啶的合成，已经开发了极其简便和有效的方法。胺，乙炔二羧酸二烷基酯和甲醛在乙二酸二铵存在下于乙醇中在回流条件下进行一锅四组分反应，可提供高收率的N-芳基-3-氨基二氢吡咯-2-一-4-羧酸酯。发现相同的条件可用于通过胺，醛和β-酮酸酯的三（伪五）组分反应合成高度取代的哌啶。发现该催化剂是可重复使用的并且可以使用多达五次而不会显着降低其活性。 图形概要

  DOI：

  10.1007/s11164-016-2512-0

文献信息

• Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Adel Beigbabaei、Anthony C. Willis

  DOI：10.1007/s13738-013-0222-8

  日期：2013.10

  Extremely facile and efficient procedures have been developed for the synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles via one-pot multi-component reactions in the presence of Al(H2PO4)3 as a heterogeneous and eco-friendly catalyst under mild conditions. The multi-component reaction of aromatic aldehydes, aromatic amines, and β-keto esters catalyzed by Al(H2PO4)3 in EtOH at room

  在Al（H 2 PO 4）3作为非均相和生态友好型催化剂的存在下，通过单锅多组分反应合成高度官能化的哌啶和二氢-2-氧基吡咯的方法极为简便有效。温和的条件。Al（H 2 PO 4）3催化的芳香醛，芳香胺和β-酮酯的多组分反应在室温下，在乙醇中提供高官能度的哌啶，收率良好至极佳。这些功能化的哌啶的结构和相对立体化学通过单X射线晶体学分析证实。发现相同的催化剂可用于在环境温度下使用胺，乙炔二羧酸二烷基酯和甲醛在甲醇中的四组分反应来合成多官能化的二氢-2-氧基吡咯。发现该催化剂是可回收的，并且可以使用多达五次而不会显着降低其活性。
• 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。
• Fe(NO₃)₃·9H₂O as Efficient Catalyst for One-pot Synthesis of Highly Functionalized Piperidines
  作者：Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Jasem Aboonajmi、Seyed Sajad Sajadikhah

  DOI：10.1002/jccs.201200421

  日期：2013.4

  Fe(NO3)3·9H2O is used as an efficient and effective catalyst for the one‐pot three‐component synthesis of highly functionalized piperidines from aromatic aldehydes, anilines and b–ketoesters in ethanol at ambient temperature. This procedure includes some important aspects like the easy work‐up, no need to column chromatography, simple and readily available precursors, and good to high yields.

  Fe（NO 3）3 ·9H 2 O可作为一种有效的催化剂，用于在环境温度下由芳族醛，苯胺和b-酮酸酯在乙醇中一锅三组分合成高度官能化的哌啶。该程序包括一些重要方面，例如易于处理，无需柱色谱，简单易用的前体以及良好到高收率。
• TiCl₂·2H₂O catalyzed one-pot synthesis of highly functionalized tetrahydropiperidines and evaluation of their antimicrobial activities
  作者：Mohsen Abbasi、Seyed Mohammad Seyedi、Hamid Sadeghian、Maryam Akhbari、Mohammadreza Enayaty、Ali Shiri

  DOI：10.1515/hc-2015-0081

  日期：2016.6.1

  One-pot condensation reaction of ethyl acetoacetate, various substituted benzaldehydes and anilines in the presence of TiCl₂·2H₂O yields highly functionalized tetrahydropiperidines. Atom economy, efficiency, and short reaction times are the advantages of the method, which is carried out under mild conditions using easily accessible and inexpensive chemicals. The antimicrobial activity of the synthesized products was evaluated against three Gram-positive and three Gram-negative bacteria, a yeast and a fungus strain using disc diffusion and minimum inhibitory concentration methods.

  一锅法合成反应中，乙酰乙酸乙酯、各种取代苯甲醛和苯胺在TiCl2·2H2O存在下反应，生成高度官能化的四氢哌啶。该方法具有原子经济性、效率高和反应时间短的优点，采用易得且廉价的化学品在温和条件下进行。合成产物的抗菌活性通过盘扩散和最小抑制浓度方法评估，对三种革兰氏阳性细菌、三种革兰氏阴性细菌、一种酵母和一种真菌菌株进行了测试。
• Green and facile synthesis of dihydropyrrol-2-ones and highly substituted piperidines using ethylenediammonium diformate (EDDF) as a reusable catalyst
  作者：Mahboobeh Zarei、Seyed Sajad Sajadikhah

  DOI：10.1007/s11164-016-2512-0

  日期：2016.9

  Abstract Extremely facile and efficient procedures have been developed for the synthesis of dihydropyrrol-2-ones and highly substituted piperidines. One-pot four-component reaction of amines, dialkyl acetylenedicarboxylates, and formaldehyde in the presence of ethylenediammonium diformate in ethanol under reflux conditions provides N-aryl-3-amino dihydropyrrol-2-one-4-carboxylates in good to high yields

  摘要 对于二氢吡咯-2-酮和高度取代的哌啶的合成，已经开发了极其简便和有效的方法。胺，乙炔二羧酸二烷基酯和甲醛在乙二酸二铵存在下于乙醇中在回流条件下进行一锅四组分反应，可提供高收率的N-芳基-3-氨基二氢吡咯-2-一-4-羧酸酯。发现相同的条件可用于通过胺，醛和β-酮酸酯的三（伪五）组分反应合成高度取代的哌啶。发现该催化剂是可重复使用的并且可以使用多达五次而不会显着降低其活性。 图形概要