methyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate | 1242430-23-4

• 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-bromophenyl)-4-((4-bromophenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 4-(4-bromoanilino)-1-(4-bromophenyl)-2,6-bis(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1242430-23-4
• 化学式: C₃₃H₃₀Br₂N₂O₂
• 分子量: 646.421
• InChiKey: BKQAIFRKWCWTHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  对甲基苯甲醛 、 乙酰乙酸甲酯 、 4-溴苯胺 在 草酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以81%的产率得到methyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  以草酸二水合物为均相催化剂一锅五组分合成高官能度哌啶

  摘要：

  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。

  DOI：

  10.1016/j.cclet.2012.03.008

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。
• 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。
• Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines
  作者：Hong-Juan Wang、Li-Ping Mo、Zhan-Hui Zhang

  DOI：10.1021/co100055x

  日期：2011.3.14

  A highly atom-economic one-pot synthesis of functionalized tetrahydropyridines by a multicomponent condensation reaction of β-keto ester, two equivalents of aromatic aldehyde, and two equivalents of amine in the presence of a catalytic amount of cerium ammonium nitrate (CAN) is reported. In this way, a series of pharmacologically interesting substituted piperidine derivatives were obtained in moderate

  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。
• Synthesis of tetrahydropyridines by one-pot multicomponent reaction using nano-sphere silica sulfuric acid
  作者：Masoume Daraei、Mohammad Ali Zolfigol、Fateme Derakhshan-Panah、Morteza Shiri、Hendrik G. Kruger、Mohammad Mokhlesi

  DOI：10.1007/s13738-014-0548-x

  日期：2015.5

  A highly efficient protocol for the synthesis of 1,2,3,4-tetrahydropyridines in the presence of nano-sphere silica sulfuric acid (NS-SSA) was used for good yields by one-pot multicomponent reaction (MCRs). The reagent nano-sphere silica sulfuric acid (NS-SSA) has several advantages, such as easy workup, nontoxicity, convenience and high yields of products.

  通过一锅多组分反应（MCR），在纳米球二氧化硅硫酸（NS-SSA）存在下合成1,2,3,4-四氢吡啶的高效方法用于获得良好的收率。该试剂纳米球二氧化硅硫酸盐（NS-SSA）具有后处理容易，无毒，方便，收率高等优点。
• Kinetics and Mechanism Investigation of the Synthesized Highly Diasteroselective Substituted Tetrahydropyridines in the Presence of La(NO3)3.6H2O as a Catalyst
  作者：Maryam Dehdab、SayyedMostafa Habibi-Khorassani、Mehdi Shahraki

  DOI：10.1007/s10562-014-1338-x

  日期：2014.11

  For the first time, kinetics and mechanism of reaction between 4-methyl-benzaldehyde, 4-bromoaniline and methyl acetoacetate is spectrally investigated in the presence of La(NO3)(3).6H(2)O as a catalyst. Based on the experiment data, the overall order of the reaction is two. The second-order rate constant dependency on the temperature was in agreement with the Arrhenius and Eyring equations. The kinetic and thermodynamic parameters of the reaction have been calculated. Furthermore, useful information was obtained from studies of the effect of solvent and concentration of reactants on the reaction rate. The results showed that the second step of the reaction mechanism is a rate-determining step (RDS). The proposed mechanism was also confirmed according to the obtained results and the steady state approximation.