methyl 2,6-bis(4-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-53-7

• 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-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: Methyl 2,6-bis(4-bromophenyl)-1-phenyl-4-(phenyl amino)-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 4-anilino-2,6-bis(4-bromophenyl)-1-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-53-7
• 化学式: C₃₁H₂₆Br₂N₂O₂
• 分子量: 618.368
• InChiKey: RALRZKGOMJQNEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  乙酰乙酸甲酯 、 对溴苯甲醛 、 苯胺 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以84%的产率得到methyl 2,6-bis(4-bromophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  硝酸铈铵催化的多组分反应有效合成功能化四氢吡啶

  摘要：

  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。

  DOI：

  10.1021/co100055x

文献信息

• Alum as an efficient catalyst for the multicomponent synthesis of functionalized piperidines
  作者：Ramneet Kaur、Annah Gupta、Kamal K. Kapoor

  DOI：10.1007/s11164-017-2979-3

  日期：2017.11

  An effective approach to the synthesis of functionalized piperidines via a one-pot multicomponent reaction of aniline, β-ketoester and aldehyde in the presence of alum as an efficient catalyst has been reported. The present procedure offers advantages such as simple workup, short reaction time and offers rapid access to a variety of functionalized piperidines.

  已经报道了在明矾作为有效催化剂的存在下通过苯胺，β-酮酸酯和醛的一锅多组分反应合成官能化哌啶的有效方法。本方法提供了诸如后处理简单，反应时间短的优点，并且提供了快速获得各种官能化哌啶的优点。
• LaCl3·7H2O as an Efficient Catalyst for One-Pot Synthesis of Highly Functionalized Piperidines via Multi-component Organic Reactions
  作者：Balijapalli Umamahesh、Venkatesan Sathesh、Gunasekar Ramachandran、Munusamy Sathishkumar、Kulatu Sathiyanarayanan

  DOI：10.1007/s10562-012-0829-x

  日期：2012.7

  The three-component one-pot synthesis of highly functionalized piperidine derivatives was carried out by condensing 1,3-dicarbonyl compounds with aromatic aldehydes and aniline using a catalytic amount (10 mol%) of LaCl3·7H2O in methanol at room temperature. The main features of current protocol include easy work up, mild reaction conditions, good yields and high atom economy.Graphical Abstract

  在室温下，使用催化量（10 mol%）的 LaCl3·7H2O 在甲醇中将 1,3-二羰基化合物与芳香醛和苯胺缩合，进行三组分一锅法合成高度官能化的哌啶衍生物。当前方案的主要特点包括易于操作、反应条件温和、产率高和原子经济性高。图形摘要
• Catalytic Asymmetric Five-Component Tandem Reaction: Diastereo- and Enantioselective Synthesis of Densely Functionalized Tetrahydropyridines with Biological Importance
  作者：Feng Shi、Wei Tan、Ren-Yi Zhu、Gui-Juan Xing、Shu-Jiang Tu

  DOI：10.1002/adsc.201300001

  日期：2013.5.17

  aldehydes and anilines have been established in the presence of a chiral phosphoric acid, affording densely functionalized tetrahydropyridines with concomitant generation of five σ bonds and two stereogenic centers in high diastereo‐ and enantioselectivities (up to >99:1 dr, 95:5 er). In addition, the first isolation and preparation of a diene species as the key intermediate of the reaction has been

  在手性磷酸存在下建立了第一个β-酮酸酯，芳香族醛和苯胺的催化不对称五组分串联反应，提供了高官能度的四氢吡啶并伴随生成五个σ键和两个立体异构中心。和对映选择性（高达> 99：1 dr，95：5 er）。另外，已经成功地实现了作为反应的关键中间体的二烯物种的首次分离和制备，从而导致了通过与原位的进一步缩合而形成所需的四氢吡啶。生成的亚胺，在一定程度上支持了串联的[4 + 2]反应路径。该方案不仅代表了这种五组分串联反应的第一个对映体选择性实例，而且还提供了前所未有的途径来获得对映体富集的具有结构多样性的四氢吡啶，这在药物化学中具有巨大的潜力。
• Organocatalyzed highly atom economic one pot synthesis of tetrahydropyridines as antimalarials
  作者：Mridul Misra、Swaroop Kumar Pandey、Vivek Parashar Pandey、Jyoti Pandey、Renu Tripathi、Rama Pati Tripathi

  DOI：10.1016/j.bmc.2008.11.062

  日期：2009.1

  A highly atom economic one pot synthesis of tetrahydropyridines was achieved by L-proline/TFA catalysed multicomponent reaction of beta-keto-esters, aromatic aldehydes and anilines. The synthesized compounds were screened against Plasmodium falciparum in vitro and one of them showed antimalarial activity with MIC as low as 0.09 mu g/mL. (C) 2008 Elsevier Ltd. All rights reserved.
• 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。