tert-butyl 1,2,6-triphenyl-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 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: tert-butyl (2S,6R)-4-anilino-1,2,6-triphenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₄H₃₄N₂O₂
• 分子量: 502.656
• InChiKey: NYVFGIAVIORZTJ-XDFJSJKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  38
• 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：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸叔丁酯 、 苯甲醛 、 苯胺 在 α-Fe₂O₃ immobilized benzimidazolium tribromide 作用下， 以 乙醇 为溶剂， 反应 10.33h， 以62%的产率得到tert-butyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  α-Fe2O3固定化的三溴化苯并咪唑作为新型可磁性回收的催化剂，用于一锅合成高官能化的哌啶

  摘要：

  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-Fe2O3和CPTES，将纳米α-Fe2O3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-Fe2O3（ClPr-Si @ Fe2O3）。合成的ClPr-Si @ Fe2O3通过苯并咪唑的共价接枝功能化，生成3-（1-苯并咪唑）Pr-Si @ Fe2O3。使其进一步与溴反应，得到固定有α-Fe2O3的苯并咪唑三溴化物（α-Fe2O3-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-Fe2O3BIM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。

  DOI：

  10.1016/j.cclet.2016.07.005

文献信息

• Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature
  作者：Goutam Brahmachari、Suvankar Das

  DOI：10.1016/j.tetlet.2012.01.042

  日期：2012.3

  diastereoselective multicomponent one-pot synthesis of a series of pharmaceutically interesting functionalized piperidine derivatives has been developed based on a low-cost and environmentally benign Bi(NO3)3·5H2O catalyst via tandem reactions of 1,3-dicarbonyl compounds, aromatic aldehydes, and various amines in ethanol at room temperature. High atom-economy, good yields, eco-friendliness, and mild reaction conditions

  基于低成本和环境友好的Bi（NO 3）3 ·5H 2 O催化剂，通过串联反应进行了简单，直接和高效的非对映选择性多组分一锅合成一系列可药用的功能化哌啶衍生物。室温下在乙醇中的1,3-二羰基化合物，芳族醛和各种胺。高原子经济性，良好的产率，生态友好性和温和的反应条件是该方案的一些重要特征。
• ‘On-Water’ Multicomponent Reaction for the Diastereoselective Synthesis of Functionalized Tetrahydropyridines and Mechanistic Insight
  作者：Asit Chakraborti、Naisargee Parikh、Sudipta Roy、Kapileswar Seth、Asim Kumar

  DOI：10.1055/s-0035-1561296

  日期：——

  An ecofriendly approach for the synthesis of highly substituted tetrahydropyridines by an on-water' multicomponent reaction has been demonstrated. The use of water as the reaction medium is essential under the catalytic influence of a surfactant. The use of a variety of anionic, cationic, and non-ionic surfactants in water was examined and the reaction was successfully catalyzed by anionic surfactants sodium dioctyl sulfosuccinate (SDOSS) and sodium dodecyl sulfate (SDS), with the former being superior. The use of an organic solvent together with a catalytic amount of sodium dioctyl sulfosuccinate to form homogeneous conditions afforded inferior yields and highlighted the specific role of water through the creation of microreactors at the water surfactant interface. A mechanistic insight for the five-component reaction leading to the formation of tetrahydropyridines is provided invoking a tandem inter- and intramolecular Mannich reaction pathway.
• 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.
• 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.