methyl-2,6-bis(4-methylphenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1242430-22-3

• 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-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate；Methyl1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di-p-tolyl-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 4-(4-methoxyanilino)-1-(4-methoxyphenyl)-2,6-bis(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1242430-22-3
• 化学式: C₃₅H₃₆N₂O₄
• 分子量: 548.682
• InChiKey: UNNOJENDCNIITC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  41
• 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：
  60
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 甲氧苯胺 、 乙酰乙酸甲酯 在 苯硼酸 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以89%的产率得到methyl-2,6-bis(4-methylphenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  高度官能化哌啶的高效一锅多组分合成

  摘要：

  摘要 以苯基硼酸为催化剂，通过取代苯胺、1,3-二羰基化合物和芳香醛的三组分反应，以优异的收率实现了简单、廉价、高效的哌啶衍生物一锅法合成。

  DOI：

  10.1515/hc-2012-0105

文献信息

• 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。
• 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。
• One-pot multicomponent synthesis of highly substituted piperidines using p-toluenesulfonic acid monohydrate as catalyst
  作者：Seyed Sajad Sajadikhah、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani、Sayyed Jalal Shams-Najafi

  DOI：10.1007/s00706-011-0671-7

  日期：2012.6

  p-Toluenesulfonic acid monohydrate (p-TsOH center dot H2O) is a highly effective and efficient catalyst for the one-pot multicomponent coupling of aldehydes, amines, and beta-ketoesters in EtOH at ambient temperature to give highly functionalized piperidines in high yields. This one-pot reaction has some important advantages such as the easy workup procedure, simple and readily available precursors, nontoxic and inexpensive catalyst, and good to high yields.