methyl 2,6-bis(3-chlorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-56-0

• 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(3-chlorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 4-(4-methoxyphenylamino)-2,6-bis(3-chlorophenyl)-1,2,5,6-tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate；methyl 2,6-bis(3-chlorophenyl)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-56-0
• 化学式: C₃₃H₃₀Cl₂N₂O₄
• 分子量: 589.518
• InChiKey: IFXZTXQNDDDPLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  甲氧苯胺 、 乙酰乙酸甲酯 、 3-氯苯甲醛 在 aluminum dihydrogen phosphate 作用下， 以 乙醇 为溶剂， 反应 14.5h， 以74%的产率得到methyl 2,6-bis(3-chlorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Al（H 2 PO 4）3作为高效且可重复使用的催化剂，用于高度官能化的哌啶和二氢-2-氧基吡咯的多组分合成

  摘要：

  在Al（H 2 PO 4）3作为非均相和生态友好型催化剂的存在下，通过单锅多组分反应合成高度官能化的哌啶和二氢-2-氧基吡咯的方法极为简便有效。温和的条件。Al（H 2 PO 4）3催化的芳香醛，芳香胺和β-酮酯的多组分反应在室温下，在乙醇中提供高官能度的哌啶，收率良好至极佳。这些功能化的哌啶的结构和相对立体化学通过单X射线晶体学分析证实。发现相同的催化剂可用于在环境温度下使用胺，乙炔二羧酸二烷基酯和甲醛在甲醇中的四组分反应来合成多官能化的二氢-2-氧基吡咯。发现该催化剂是可回收的，并且可以使用多达五次而不会显着降低其活性。

  DOI：

  10.1007/s13738-013-0222-8

文献信息

• 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。
• SULFAMIC ACID CATALYZED FIVE COMPONENT REACTION FOR EFFICIENT AND ONE-POT SYNTHESIS OF DENSELY FUNCTIONALIZED TETRAHYDROPYRIDINE SCAFFOLD
  作者：ANIKETP SARKATE、JAIPRAKASH N SANGSHETTI、NANASAHEB B DHARBALE、AJINKYA P SARKATE、DEVANAND B SHINDE

  DOI：10.4067/s0717-97072015000100012

  日期：——

  acid in One-pot assembling of aromatic aldehydes, aromatic amines and β-keto esters to afford densely functionalized tetrahydropyridines in 70-89% yield has been presented. The advantage of sulfamic acid against other catalysts in terms of yield has been studied. The effect of different solvents on reaction time and yield has also been studied. Easy work up and mild reaction condition are the advantages

  已经提出了氨基磺酸在芳族醛，芳族胺和β-酮酯的一锅组装中以70-89％的产率提供致密官能化的四氢吡啶的用途。研究了氨基磺酸相对于其他催化剂在产率方面的优势。还研究了不同溶剂对反应时间和产率的影响。该方法的优点是易于后处理，反应条件温和。
• 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.
• 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.