ethyl 1-(4-fluorophenyl)-4-((4-fluorophenyl)amino)-2,6-diphenyl-1,2,5,6 tetrahydropyridine-3-carboxylate | 1463927-14-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 1-(4-fluorophenyl)-4-((4-fluorophenyl)amino)-2,6-diphenyl-1,2,5,6 tetrahydropyridine-3-carboxylate
• 英文别名: ethyl 4-(4-fluoroanilino)-1-(4-fluorophenyl)-2,6-diphenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1463927-14-1
• 化学式: C₃₂H₂₈F₂N₂O₂
• 分子量: 510.583
• InChiKey: SPAMZEYQTMKKQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  41.6
• 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 、 苯甲醛 、 4-氟苯胺 在 silica sulfuric acid 作用下， 以 乙醇 为溶剂， 反应 9.0h， 以74%的产率得到ethyl 1-(4-fluorophenyl)-4-((4-fluorophenyl)amino)-2,6-diphenyl-1,2,5,6 tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  二氧化硅硫酸催化的五取代四氢吡啶的五组分高效合成

  摘要：

  据报道，一种高原子经济的一锅法合成方法是通过二当量的芳族醛，两当量的芳族苯胺和一当量的二氧化硅硫酸催化的五组分缩合反应来合成五取代的四氢吡啶。在该反应中，在一个锅中最多只有五个副产物形成了五个新的键和一个新的环。

  DOI：

  10.1002/jhet.1744

文献信息

• Alum as an efficient catalyst for the multicomponent synthesis of functionalized piperidines
  作者：Ramneet Kaur、Annah Gupta、Kamal K. Kapoor

  DOI：10.1007/s11164-017-2979-3

  日期：2017.11

  An effective approach to the synthesis of functionalized piperidines via a one-pot multicomponent reaction of aniline, β-ketoester and aldehyde in the presence of alum as an efficient catalyst has been reported. The present procedure offers advantages such as simple workup, short reaction time and offers rapid access to a variety of functionalized piperidines.

  已经报道了在明矾作为有效催化剂的存在下通过苯胺，β-酮酸酯和醛的一锅多组分反应合成官能化哌啶的有效方法。本方法提供了诸如后处理简单，反应时间短的优点，并且提供了快速获得各种官能化哌啶的优点。
• Cyanuric chloride catalyzed metal-free mild protocol for the synthesis of highly functionalized tetrahydropyridines
  作者：Rathinam Ramesh、Subramani Maheswari、Mani Arivazhagan、Jan Grzegorz Malecki、Appaswami Lalitha

  DOI：10.1016/j.tetlet.2017.08.074

  日期：2017.10

  condensation of ethyl acetoacetate, anilines and aromatic aldehydes under mild reaction conditions has been described. This domino strategy allows rapid cyclization in the presence of 10 mol% of cyanuric chloride as a source of hydrochloric acid to afford the desired target skeletons in excellent yields. The present protocol offers prominent advantages of simple operational procedure, metal-free organocatalyst

  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。
• Aluminized polyborate: a novel catalyst for the multicomponent solvent-free synthesis of alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxylates
  作者：Anil S. Mali、Chinmay S. Potnis、Ganesh U. Chaturbhuj

  DOI：10.1007/s13738-018-1340-0

  日期：2018.6

  An efficient and simple method for the one-pot three-component synthesis of alkyl 1,2,6-trisubstituted-4-[(hetero)arylamino]-1,2,5,6-tetrahydropyridine-3-carboxylates was developed using aromatic aldehyde, amine and β-ketoesters catalyzed by aluminized polyborate, an efficient reusable catalyst under solvent-free condition. Aluminized polyborate has advantageous of cost, ecologically benefits, accessible preparation and recyclability up to five cycles along with high product yield and simplicity.

  在无溶剂条件下，利用可重复使用的高效催化剂聚硼酸铝催化芳香醛、胺和β-酮酯，开发了一种高效、简单的单锅三组分合成 1,2,6-三取代-4-[（杂）芳基氨基]-1,2,5,6-四氢吡啶-3-羧酸烷基酯的方法。铝化聚硼酸盐具有成本低、生态效益好、易于制备、可循环使用五次、产品收率高和操作简单等优点。
• Polyphosphoric acid–zirconia pillared clay composite catalytic system for efficient multicomponent one pot synthesis of tetrahydropyridines under environmentally benign conditions
  作者：Purabi Kar、B.G. Mishra、S.R. Pradhan

  DOI：10.1016/j.molcata.2014.02.024

  日期：2014.6

  A series of zirconia pillared clay-polyphosphoric acid (PPA) composites are synthesized by adopting different preparative strategies. Initially, PPA is intercalated to the clay matrix with and without the use of structure expanding agent (CTAB). Subsequently, the PPA-clay composite is pillared with Zrpolycation to form the composite materials. In an alternate approach, Zr-pillared clay is synthesized by insertion of Zr-polycation, which is then used for dispersion of PPA moiety in the pillared clay matrix. The synthesized composites are characterized by XRD, FTIR, UV-vis, TGA, EDX, FE-SEM and sorptometric techniques. XRD study indicated an expansion in the clay structure after intercalation of PPA as well as the Zr-polycations. The FTIR spectra exhibit characteristic vibrational features of the clay sheet as well as PPA moiety indicating the structural stability of the composite materials. The phosphorous content in the composite samples is analyzed using EDX study. FE-SEM study indicated morphological changes upon intercalation of PPA and Zr-polycations to the clay matrix. The catalytic activity of the composite catalysts has been examined for the synthesis of tetrahydropyridines under environmental benign conditions by one pot multicomponent condensation of beta-dicarbonyl compounds, substituted anilines and substituted benzaldehydes. The PPA intercalated clay pillared with Zr polycations (PPA-ZrP) is found to be highly efficient for the synthesis of structurally diverse substituted tetrahydropyridines under mild conditions. (C) 2014 Elsevier B.V. All rights reserved.