methyl 2,6-bis(4-methylphenyl)-1-benzyl-4-(benzylamino)-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(4-methylphenyl)-1-benzyl-4-(benzylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: 1-benzyl-4-benzylamino-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester；methyl 1-benzyl-4-(benzylamino)-1,2,5,6-tetrahydro-2,6-dip-tolylpyridine-3-carboxylate；methyl (2S,6R)-1-benzyl-4-(benzylamino)-2,6-bis(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₅H₃₆N₂O₂
• 分子量: 516.683
• InChiKey: NYXLWYXOLIXRCA-UZNNEEJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 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 、 苄胺 在 silica gel 作用下， 反应 4.0h， 以79%的产率得到methyl 2,6-bis(4-methylphenyl)-1-benzyl-4-(benzylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  无溶剂二氧化硅促进的多组分缩合：高度官能化的哌啶的合成

  摘要：

  摘要 硅胶是一种在室温下无溶剂条件下通过一锅三组分醛，胺和 β- 酮酸酯的缩合反应，以高产率高收率合成非对映特异性官能化哌啶的有效且可重复使用的介质。 。使用这种对环境无害，不易燃且无毒的反应介质，非色谱纯化，硅胶的可重复使用性和操作简便性是本方法的显着优势。该程序适用于哌啶衍生物的大规模合成，代表了绿色合成方案。 图形概要

  DOI：

  10.1007/s11164-014-1774-7

文献信息

• Efficient one-pot synthesis of functionalized piperidine scaffolds via ZrOCl2·8H2O catalyzed tandem reactions of aromatic aldehydes with amines and acetoacetic esters
  作者：Sarita Mishra、Rina Ghosh

  DOI：10.1016/j.tetlet.2011.03.116

  日期：2011.6

  A highly efficient diastereoselective one-pot synthesis of functionalized piperidines has been developed based on an aqua-compatible ZrOCl2·8H2O catalyst via tandem reactions of aromatic aldehydes, amines, and acetoacetic esters.

  通过与水相容的ZrOCl 2 ·8H 2 O催化剂，通过芳族醛，胺和乙酰乙酸酯的串联反应，开发了一种高效的非对映选择性一锅合成的官能化哌啶。
• Trityl chloride as an efficient organic catalyst for one-pot, five-component and diastereoselective synthesis of highly substituted piperidines
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Anthony C. Willis

  DOI：10.1007/s11164-012-0997-8

  日期：2014.2

  chloride is used as an efficient organic catalyst for the one-pot, five-component and diastereoselective synthesis of highly substituted piperidines by means of reaction between aromatic aldehydes, amines and β -ketoesters in methanol at 50 °C. The structure as well as relative stereochemistry of products was confirmed by single X-ray crystallographic analysis. This homogeneous catalyst procedure includes

  摘要 三苯甲基氯是一种有效的有机催化剂，可通过芳香醛，胺和 β- 酮酸酯在甲醇中于50°C下反应，一锅，五组分和非对映选择性地合成高度取代的哌啶 。通过单X射线晶体分析证实了产物的结构以及相对立体化学。该均相催化剂程序包括一些重要方面，例如易于后处理，非对映选择性，简单易用的前体，廉价的催化剂，相对短的反应时间以及良好的高收率。 图形概要
• Synthesis of highly functionalized piperidines by one-pot multicomponent reaction using tetrabutylammonium tribromide (TBATB)
  作者：Abu T. Khan、Mohan Lal、Md. Musawwer Khan

  DOI：10.1016/j.tetlet.2010.06.069

  日期：2010.8

  Tetrabutylammonium tribromide (TBATB) has been found to be an efficient catalyst for the one-pot synthesis of highly substituted piperidines through a combination of 1,3-dicarbonyl compounds, aromatic aldehydes, and various amines in ethanol at room temperature. Atom economy, good yields, environmentally benign, and mild reaction conditions are some of the important features of this protocol.

  已发现三溴化四丁基铵（TBATB）是在室温下通过乙醇中1,3-二羰基化合物，芳族醛和各种胺的组合，一锅法合成高度取代的哌啶的有效催化剂。原子经济，产率高，环境友好，反应条件温和是该协议的一些重要特征。
• Iodine catalyzed one-pot five-component reactions for direct synthesis of densely functionalized piperidines
  作者：Abu T. Khan、Md. Musawwer Khan、Kranthi K.R. Bannuru

  DOI：10.1016/j.tet.2010.07.075

  日期：2010.9

  convenient one-pot multicomponent reaction (MCR) has been developed for the synthesis of highly functionalized piperidines catalyzed by molecular iodine. This strategy demonstrated five-component reactions of 1,3-dicarbonyl compounds, amines and aromatic aldehydes in methanol using 10 mol % of iodine at room temperature. This methodology provides an alternative approach for easy access of highly and fully

  已经开发了一种简单方便的一锅多组分反应（MCR），用于合成由分子碘催化的高度官能化的哌啶。该策略证明了在室温下使用10 mol％的碘在甲醇中进行1,3-二羰基化合物，胺和芳香醛的五组分反应。该方法学提供了另一种方法，可以使用三种容易获得的起始原料，以中等到良好的收率轻松获得高度和完全取代的哌啶。值得注意的是，与现有方法相比，该方法温和，便宜，简单，适用于多种基材并且对环境友好。此处介绍了综合和机理研究。
• Effects of Substituents in the β-Position of 1,3-Dicarbonyl Compounds in Bromodimethylsulfonium Bromide-Catalyzed Multicomponent Reactions: A Facile Access to Functionalized Piperidines
  作者：Abu T. Khan、Tasneem Parvin、Lokman H. Choudhury

  DOI：10.1021/jo8014962

  日期：2008.11.7

  w1,3-Dicarbonyl compounds can be converted to Mannich-type products A or highly functionalized piperidines B in the presence of a catalytic amount of bromodimethylsulfonium bromide (BDMS). The combination of aromatic aldehyde, amine, and 1,3-dicarbonyl compounds in the presence of a catalytic amount of BDMS leads to the formation of Mannich-type product A when R is a non-enolizable carbon or an alkoxy group, whereas in cases when R = CH3, the same combination yielded highly functionalized piperidines B. A synthetic study and mechanistic proposal are presented.