tert-butyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-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: tert-butyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: 1-phenyl-4-phenylamino-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid tert-butyl ester；tert-butyl (2S,6R)-4-anilino-2,6-bis(4-methylphenyl)-1-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₆H₃₈N₂O₂
• 分子量: 530.71
• InChiKey: XPETVBAIFYEKCN-UZNNEEJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  乙酰乙酸叔丁酯 、 对甲基苯甲醛 、 苯胺 在 碘 作用下， 以 甲醇 为溶剂， 反应 10.33h， 以68%的产率得到tert-butyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  碘催化一锅五组分反应，直接合成高密度官能化哌啶

  摘要：

  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。

  DOI：

  10.1016/j.tet.2010.07.075

文献信息

• 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。
• Solvent-free silica-promoted multicomponent condensation: synthesis of highly functionalized piperidines
  作者：Sudarshan Das、Avik Kumar Bagdi、Sougata Santra、Adinath Majee、Alakananda Hajra

  DOI：10.1007/s11164-014-1774-7

  日期：2015.9

  Abstract Silica gel has been found to be an efficient and reusable medium for the synthesis of diastereospecific functionalized piperidines in good to high yields by a one-pot three-component condensation of aldehyde, amine and β -ketoester under solvent-free conditions at room temperature. Using this environmentally benign, non-inflammable and non-toxic reaction medium, the non-chromatographic purification

  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
• α-Fe2O3 immobilized benzimidazolium tribromide as novel magnetically retrievable catalyst for one-pot synthesis of highly functionalized piperidines
  作者：Bappi Paul、Sethumathavan Vadivel、Siddhartha Sankar Dhar

  DOI：10.1016/j.cclet.2016.07.005

  日期：2016.11

  was functionalized via covalent grafting of benzimidazole to produce 3-(1-benzimidazole)Pr-Si@Fe2O3. This was further reacted with bromine to afford α-Fe2O3 immobilized benzimidazolium tribromide (α-Fe2O3-BIM tribromide). This ionic liquid (IL) α-Fe2O3 BIM tribromide was characterized by FT-IR, XRD, TEM, SEM, TGA, VSM, EDX and BET analysis. The as-synthesized IL tribromide was used as catalyst for

  沉淀法接着煅烧法制备了纳米结构的α-Fe2O3。十六烷基三甲基溴化铵（CTAB）用作表面活性剂。然后通过在室温下混合α- 和CPTES，将纳米α- 与（3-氯丙基）-三乙氧基硅烷（CPTES）进行硅烷化，以制备硅烷包覆的α- （ClPr-Si @ ）。合成的ClPr-Si @ 通过苯并咪唑的共价接枝功能化，生成3-（1-苯并咪唑）Pr-Si @ 。使其进一步与溴反应，得到固定有α- 的苯并咪唑三溴化物（α- -BIM三溴化物）。通过FT-IR，XRD，TEM，SEM，TGA，VSM，EDX和BET分析对这种离子液体（IL）α- BIM三溴化物进行了表征。合成后的IL三溴化物用作一锅合成高取代哌啶的催化剂。
• Synthesis of functionalized dihydro-2-oxypyrroles and tetrahydropyridines using 2,6-pyridinedicarboxylic acid as an efficient and mild organocatalyst
  作者：Md. Musawwer Khan、Sarfaraz Khan、Safia Iqbal、Saigal Saigal、Raveed Yousuf

  DOI：10.1039/c6nj01170e

  日期：——

  developed for the synthesis of diversely functionalized dihydro-2-oxypyrroles and tetrahydropyridines. One-pot four-component reaction of dialkyl acetylenedicarboxylates, amines and formaldehyde in the presence of 2,6-pyridinedicarboxylic acid in methanol at room temperature provides dihydro-2-oxypyrroles. The combination of β-ketoesters, aromatic aldehydes and amines yielded tetrahydropyridine derivatives

  已经开发了简单有效的方案，用于合成功能多样的二氢-2-氧基吡咯和四氢吡啶。乙炔基二羧酸二烷基酯，胺和甲醛在2,6-吡啶二羧酸存在下于室温下在甲醇中进行一锅四组分反应可得到二氢-2-氧基吡咯。在相同的反应条件下，β-酮酸酯，芳族醛和胺的组合产生四氢吡啶衍生物。这些方法的显着特征是温和的反应条件，缩短的反应时间，中等至高收率，适用于广泛的底物并且无需繁琐的柱色谱分离。
• 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.