ethyl 4-(4-tolylamino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydro-1-(4-tolyl)pyridine-3-carboxylate | 1413946-21-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 4-(4-tolylamino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydro-1-(4-tolyl)pyridine-3-carboxylate
• 英文别名: 3-Pyridinecarboxylic acid, 2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydro-1-(4-methylphenyl)-4-[(4-methylphenyl)amino]-, ethyl ester；ethyl 2,6-bis(4-fluorophenyl)-4-(4-methylanilino)-1-(4-methylphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1413946-21-0
• 化学式: C₃₄H₃₂F₂N₂O₂
• 分子量: 538.637
• InChiKey: MUHVQXBZPMPNAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  40
• 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：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对氟苯甲醛 、 乙烷,三氯氟- 在 silica sulfuric acid 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以64%的产率得到ethyl 4-(4-tolylamino)-2,6-bis(4-fluorophenyl)-1,2,5,6-tetrahydro-1-(4-tolyl)pyridine-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

• 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.
• Highly functionalized tetrahydropyridines are cytotoxic and selective inhibitors of human puromycin sensitive aminopeptidase
  作者：Raghunath Aeluri、Roopa Jones Ganji、Anil Kumar Marapaka、Vijaykumar Pillalamarri、Manjula Alla、Anthony Addlagatta

  DOI：10.1016/j.ejmech.2015.10.026

  日期：2015.12

  Efficient one-pot five-component synthetic protocols for highly functionalized tetrahydropyridines (THPs) and their biological evaluation have been illustrated. Synthesis of novel functionalized tetrahydropyridines containing differential substitutions at 2,6-positions has been achieved via a modified MCR. Cytotoxic studies of 23 synthesized compounds have been carried out against three different cell lines, namely A-549, HeLa and HepG2, wherein some compounds have displayed appreciable cytotoxicity. Further, investigation of enzyme inhibition by the synthesized THPs has been carried out against four members of M1 family aminopeptidases. Several compounds have selectively inhibited only one member of this enzyme family i.e., human puromycin sensitive aminopeptidase (hPSA). Among the compounds; 4h, 9b, 9e and 10a demonstrated best inhibition against hPSA. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Silica Sulfuric Acid-Catalyzed Five-component Efficient Synthesis of Five-Substituted Tetrahydropyridines
  作者：Xiao-xiao Zhang、Yu Wan、Li-ling Pang、Hai-ying Wang、Ling-ling Zhao、Chao Wang、Shu Ying Hang、Gui Xiang Liu、Liang-Feng Chen、Hui Wu

  DOI：10.1002/jhet.1744

  日期：2014.3

  A highly atom‐economic one‐pot synthesis of five‐substituted tetrahydropyridines via a five‐component condensation of two equivalents of aromatic aldehyde, two equivalents of aromatic aniline, and one equivalent of β‐keto ester catalyzed by silica sulfuric acid is reported. In this reaction, up to five new bonds and one new ring were formed in one pot with water as the only one by‐product.

  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。