ethyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1229848-15-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: Ethyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；ethyl 4-anilino-2,6-bis(4-methylphenyl)-1-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1229848-15-0
• 化学式: C₃₄H₃₄N₂O₂
• 分子量: 502.656
• InChiKey: NBVXLYNBQKTYAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  对甲基苯甲醛 、 乙酰乙酸乙酯 、 苯胺 在 MgFe₂O₄/cellulose/SO₃H nanocomposite 作用下， 以 neat (no solvent) 为溶剂， 反应 0.42h， 以95%的产率得到ethyl 2,6-bis(4-methylphenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  MgFe2O4/cellulose/SO3H nanocomposite: a new biopolymer-based nanocatalyst for one-pot multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones

  摘要：

  制备了一种新型生物聚合物纤维素基磁性异相催化剂--MgFe2O4/纤维素/SO3H 纳米复合材料。利用傅立叶变换红外光谱、X 射线衍射、能量色散 X 射线、场发射扫描电子显微镜、热分析（TG、DTG 和 DSC）、动态光散射和振动样品磁力计测量来表征该催化剂。然后，在无溶剂条件下，将其作为一种廉价的绿色催化剂有效地应用于两种多组分合成多取代四氢吡啶和二氢嘧啶酮的过程中。该纳米催化剂可多次回收和重复使用，而不会明显丧失催化活性。

  DOI：

  10.1007/s13738-017-1120-2

文献信息

• Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahydropyridines using a nanostructured silica-based catalyst under mild conditions
  作者：Navid Irannejad-Gheshlaghchaei、Seyed Sajad Sajadikhah

  DOI：10.2174/1386207323666200914092345

  日期：2020.9.14

  Mass spectroscopy. Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano-[DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes

  目的和目的：Nano-2-[N',N'-dimethyl-N'-(silica-n-丙基)ethanaminium chloride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4])用作一种高效的非均相二氧化硅基纳米结构催化剂，用于合成 1-硫代氨基烷基-2-萘酚和取代的四氢吡啶。 材料与方法：预期产品在温和条件下制备。在这项工作中，合成了三种新型 1-硫代酰胺烷基-2-萘酚和两种新型四氢吡啶衍生物，并通过 IR、1 H 和13 C NMR 和质谱进行了表征。 结果：纳米-[DSPECDA][HSO 4 ] 催化2-萘酚与芳醛和硫代乙酰胺在绿色、温和、无溶剂条件下的一锅多组分缩合反应得到高收率的1-硫代氨基烷基-2-萘酚。该纳米催化剂还用于在无溶剂和温和条件下通过苯胺、芳基醛和乙酰乙酸乙酯的一锅多组分反应制备官能化四氢吡啶。 结论：
• Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Adel Beigbabaei、Anthony C. Willis

  DOI：10.1007/s13738-013-0222-8

  日期：2013.10

  Extremely facile and efficient procedures have been developed for the synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles via one-pot multi-component reactions in the presence of Al(H2PO4)3 as a heterogeneous and eco-friendly catalyst under mild conditions. The multi-component reaction of aromatic aldehydes, aromatic amines, and β-keto esters catalyzed by Al(H2PO4)3 in EtOH at room

  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。
• One-pot five-component synthesis of highly functionalized piperidines using oxalic acid dihydrate as a homogenous catalyst
  作者：Seyed Sajad Sajadikhah、Malek Taher Maghsoodlou、Nourallah Hazeri、Sayyed Mostafa Habibi-Khorassani、Anthony C. Willis

  DOI：10.1016/j.cclet.2012.03.008

  日期：2012.5

  An efficient green protocol is described for the preparation of highly functionalized piperidines via a one-pot five-component reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of oxalic acid dihydrate as catalyst in ethanol at ambient temperature. The structure as well as the relative stereochemistry of these compounds was confirmed by single X-ray crystallographic analysis

  描述了一种有效的绿色方案，用于在乙二酸二水合物作为催化剂在乙醇中，环境温度下，通过芳族醛，苯胺和β-酮酸酯之间的一锅五组分反应制备高官能化的哌啶。这些化合物的结构和相对立体化学通过单X射线晶体学分析证实。
• Diastereoselective Synthesis of Symmetrical and Unsymmetrical Tetrahydropyridines Catalyzed by Bi(III) Immobilized on Triazine Dendrimer Stabilized Magnetic Nanoparticles
  作者：Beheshteh Asadi、Amir Landarani-Isfahani、Iraj Mohammadpoor-Baltork、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani、Hadi Amiri Rudbari

  DOI：10.1021/acscombsci.6b00180

  日期：2017.6.12

  the first time from a five-component Fe3O4@TDSN-Bi(III)-catalyzed reaction of aryl aldehydes, aryl amines, and ethyl acetoacetate. This magnetically separable catalyst enabled the selective incorporation of two different aryl amines or two different aryl aldehydes into the product, and provided excellent yields, short reaction times, mild reaction conditions, satisfactory catalyst recyclability, and

  首次从五组分Fe 3 O 4 TDSN-Bi（III）催化的芳基醛，芳基胺和乙酰乙酸乙酯的反应中获得不对称的1,2,5,6-四氢吡啶-3-羧酸酯。该磁性可分离的催化剂能够将两种不同的芳基胺或两种不同的芳基醛选择性地掺入产物中，并提供优异的收率，较短的反应时间，温和的反应条件，令人满意的催化剂可回收性和较低的催化剂负载量。
• 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。