methyl 2,6-bis(4-fluorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-49-1

• 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-fluorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl-4-(4-methoxyphenylamino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate；methyl 2,6-bis(4-fluorophenyl)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-49-1
• 化学式: C₃₃H₃₀F₂N₂O₄
• 分子量: 556.609
• InChiKey: RHCXXCDKSISLDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 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：
  8

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 甲氧苯胺 、 乙酰乙酸甲酯 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以82%的产率得到methyl 2,6-bis(4-fluorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-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

• 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。
• 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。
• 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.
• 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.