ethyl 4-(4-methoxyphenylamino)-2,6-bis(4-chlorophenyl)-1,2,5,6-tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate | 1415425-07-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 4-(4-methoxyphenylamino)-2,6-bis(4-chlorophenyl)-1,2,5,6-tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate
• 英文别名: ethyl 2,6-bis(4-chlorophenyl)-1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 2,6-bis(4-chlorophenyl)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate；Ethyl 2,6-bis(4-chlorophenyl)-4-(4-methoxy-anilino)-1-(4-methoxyphenyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylate；ethyl 2,6-bis(4-chlorophenyl)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1415425-07-8
• 化学式: C₃₄H₃₂Cl₂N₂O₄
• 分子量: 603.545
• InChiKey: WTCHAYFUDFDXST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  乙酰乙酸乙酯 、 4-氯苯甲醛 、 甲氧苯胺 在 三聚氯氰 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以89%的产率得到ethyl 4-(4-methoxyphenylamino)-2,6-bis(4-chlorophenyl)-1,2,5,6-tetrahydro-1-(4-methoxyphenyl)pyridine-3-carboxylate
  参考文献：
  名称：

  氰尿酰氯催化的无金属温和规程，用于合成高度官能化的四氢吡啶

  摘要：

  环境友好，容易和优雅的合成方法进行了一系列不同的2,6-二芳基四氢吡啶-3-羧酸盐的方便访问经由一釜，乙酰乙酸乙酯，苯胺和在温和的芳香醛的伪五组分缩合已经描述了反应条件。这种多米诺骨牌策略允许在10摩尔％的氰尿酰氯作为盐酸源的情况下快速环化，从而以优异的收率提供所需的目标骨架。本协议提供了以下优点：操作步骤简单，无金属的有机催化剂，实用且坚固的基材范围。

  DOI：

  10.1016/j.tetlet.2017.08.074

文献信息

• NO2-Fe(III)PcCl@C -catalyzed one-pot synthesis of tetrahydropyridine derivatives
  作者：Jiao-dan Wang、Qiao-li Lin、Jun Qiu、Xiao-feng Gou、Cheng-wen Hua、Jun-long Zhao、Bang Chen

  DOI：10.1134/s1070363217040259

  日期：2017.4

  efficient, one-pot synthesis of functionalized tetrahydropyridines by multicomponent condensation of ethyl acetoacetate, two equivalents of aromatic aldehyde, and aromatic amine in the presence of a catalytic amount of NO2-Fe(III)PcCl@C is reported. In this way, a series of pharmacologically interesting substituted pyridine derivatives were obtained in moderate to good yields.

  据报道，在催化量的NO 2 -Fe（III）PcCl @ C存在下，通过乙酰乙酸乙酯，两当量的芳族醛和芳族胺的多组分缩合，高效，一锅法合成官能化的四氢吡啶。以这种方式，以中等至良好的产率获得了一系列药理学上有趣的取代吡啶衍生物。
• Design, preparation and characterization of a new ionic liquid, 1,3-disulfonic acid benzimidazolium chloride, as an efficient and recyclable catalyst for the synthesis of tetrahydropyridine under solvent-free conditions
  作者：Mohsen Abbasi

  DOI：10.1039/c5ra10699k

  日期：——

  acid benzimidazolium chloride as a new ionic liquid, is synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR as well as mass spectra. This ionic liquid is used as an efficient, homogeneous and recyclable catalyst for synthesis of highly functionalized tetrahydropyridine via one-pot multi-component condensation of aromatic aldehydes, ethyl acetoacetate, and anilines under solvent-free

  在目前的工作中，合成了作为新型离子液体的1,3-二磺酸苯并咪唑鎓盐，并对其FT-IR，1 H NMR，13 C NMR以及质谱进行了表征。该离子液体用作高效，均质和可回收的催化剂，可通过以下途径合成高度官能化的四氢吡啶在无溶剂条件下，单锅多组分缩合芳族醛，乙酰乙酸乙酯和苯胺。当前的合成路线是一种绿色方案，具有几个优点，例如产品收率高，反应时间短，反应条件温和，化学废物最少，后处理程序容易。此外，该催化剂可以重复使用和回收至少四次而没有明显的活性损失。
• Synthesis, characterization and first application of keggin-type heteropoly acids supported on silica coated NiFe₂O₄as novel magnetically catalysts for the synthesis of tetrahydropyridines
  作者：Hossein Eshghi、Amir Khojastehnezhad、Farid Moeinpour、Mehdi Bakavoli、Seyed Mohammad Seyedi、Mohsen Abbasi

  DOI：10.1039/c4ra05133e

  日期：——

  In this study, two heteroploly acids with Keggin structures (phosphotungestic acid (PWA) and phosphomolybdic acid (PMA)) have been supported on silica coated nickel ferrite nanoparticles (NiFe2O4@SiO2). The synthesized catalysts were characterized by several methods (FT-IR, SEM, TEM, VSM, XRD, BET and ICP-AES), and the catalytic activities of these new and magnetic catalysts in synthesis of tetrahydropyridine derivatives have been investigated. These new catalysts showed that they can carry out reactions at room temperature in a short time and under solvent-free conditions. Moreover, the obtained results indicated that PWA supported NiFe2O4@SiO2 is a stronger acid than PMA to run these reactions. More importantly, the catalysts were easily isolated from the reaction mixture by a magnetic bar and reused at least five times without significant degradation in their activities.

  在这项研究中，采用Keggin结构的两种异源多酸（磷钨酸（PWA）和磷钼酸（PMA））被负载在涂有二氧化硅的镍铁氧体纳米颗粒（NiFe2O4@SiO2）上。合成的催化剂采用多种方法进行表征（FT-IR、SEM、TEM、VSM、XRD、BET和ICP-AES），并研究了这些新型磁性催化剂在合成四氢吡啶衍生物中的催化活性。这些新催化剂表明，它们能够在室温下、短时间内及无溶剂条件下进行反应。此外，获得的结果表明，负载PWA的NiFe2O4@SiO2在进行这些反应时比PMA具有更强的酸性。更重要的是，催化剂可以通过磁棒轻松从反应混合物中分离出来，并在未显著降低活性的情况下重复使用至少五次。
• Mohammadi, Seddigheh; Ghazanfari, Dadkhoda; Karimi-Jaberi, Zahed, Revue Roumaine de Chimie, 2017, vol. 62, # 11, p. 825 - 829
  作者：Mohammadi, Seddigheh、Ghazanfari, Dadkhoda、Karimi-Jaberi, Zahed

  DOI：——

  日期：——
• The first example of glucose-containing carbene Brønsted acid synthesis and catalysis: efficient synthesis of five substituted tetrahydropyridines
  作者：Qiu-ju Zhou、Yu Wan、Xiao-xiao Zhang、Li-zhuo Zhang、Huan Zou、Hao Cui、Sheng-liang Zhou、Hai-ying Wang、Hui Wu

  DOI：10.1016/j.tet.2015.06.062

  日期：2015.9

  beta-1-Imidazole-2,3,4,6-tetrasulfonic-D-glucopyranosyl bisulfate ([Bmim-G(SO3H)(4)](+)[HSO4](-), I) was synthesized for the first time and used as an efficient catalyst to prepare five-substituted tetrahydropyridines via the three-component condensation of aromatic aldehyde, aromatic aniline and ethyl acetoacetate in ethanol at 40 degrees C. Six bonds were cleaved while five new bonds and one new ring were formed in one-pot with water as the only one by-product in this highly atom-economic reaction. The work opens up a new and efficient synthesis and application of sugar-containing carbene Bronsted acid. (C) 2015 Published by Elsevier Ltd.