ethyl 2,6-bis(3-chlorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-80-0

• 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(3-chlorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: ethyl 2,6-bis(3-chlorophenyl)-4-(4-methoxyanilino)-1-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-80-0
• 化学式: C₃₄H₃₂Cl₂N₂O₄
• 分子量: 603.545
• InChiKey: GQVGSIVEBRSFBK-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 、 甲氧苯胺 、 3-氯苯甲醛 在 tin(II) chloride dihydrate 作用下， 以 乙醇 为溶剂， 反应 4.33h， 以90%的产率得到ethyl 2,6-bis(3-chlorophenyl)-1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  TiCl₂·2H₂O catalyzed one-pot synthesis of highly functionalized tetrahydropiperidines and evaluation of their antimicrobial activities

  摘要：

  一锅法合成反应中，乙酰乙酸乙酯、各种取代苯甲醛和苯胺在TiCl2·2H2O存在下反应，生成高度官能化的四氢哌啶。该方法具有原子经济性、效率高和反应时间短的优点，采用易得且廉价的化学品在温和条件下进行。合成产物的抗菌活性通过盘扩散和最小抑制浓度方法评估，对三种革兰氏阳性细菌、三种革兰氏阴性细菌、一种酵母和一种真菌菌株进行了测试。

  DOI：

  10.1515/hc-2015-0081

文献信息

• An efficient one-pot multi-component synthesis of highly functionalized piperidines
  作者：Santosh V. Goswami、Prashant B. Thorat、Sudhakar R. Bhusare

  DOI：10.1515/hc-2012-0105

  日期：2012.12.1

  Abstract A simple, inexpensive and efficient one-pot synthesis of piperidine derivatives was achieved in excellent yield via the three-component reaction of substituted aniline, 1,3-dicarbonyl compound and aromatic aldehyde using phenylboronic acid as catalyst.

  摘要 以苯基硼酸为催化剂，通过取代苯胺、1,3-二羰基化合物和芳香醛的三组分反应，以优异的收率实现了简单、廉价、高效的哌啶衍生物一锅法合成。
• Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines
  作者：Hong-Juan Wang、Li-Ping Mo、Zhan-Hui Zhang

  DOI：10.1021/co100055x

  日期：2011.3.14

  A highly atom-economic one-pot synthesis of functionalized tetrahydropyridines by a multicomponent condensation reaction of β-keto ester, two equivalents of aromatic aldehyde, and two equivalents of amine in the presence of a catalytic amount of cerium ammonium nitrate (CAN) is reported. In this way, a series of pharmacologically interesting substituted piperidine derivatives were obtained in moderate

  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。
• 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.
• TiCl₂·2H₂O catalyzed one-pot synthesis of highly functionalized tetrahydropiperidines and evaluation of their antimicrobial activities
  作者：Mohsen Abbasi、Seyed Mohammad Seyedi、Hamid Sadeghian、Maryam Akhbari、Mohammadreza Enayaty、Ali Shiri

  DOI：10.1515/hc-2015-0081

  日期：2016.6.1

  One-pot condensation reaction of ethyl acetoacetate, various substituted benzaldehydes and anilines in the presence of TiCl₂·2H₂O yields highly functionalized tetrahydropiperidines. Atom economy, efficiency, and short reaction times are the advantages of the method, which is carried out under mild conditions using easily accessible and inexpensive chemicals. The antimicrobial activity of the synthesized products was evaluated against three Gram-positive and three Gram-negative bacteria, a yeast and a fungus strain using disc diffusion and minimum inhibitory concentration methods.

  一锅法合成反应中，乙酰乙酸乙酯、各种取代苯甲醛和苯胺在TiCl2·2H2O存在下反应，生成高度官能化的四氢哌啶。该方法具有原子经济性、效率高和反应时间短的优点，采用易得且廉价的化学品在温和条件下进行。合成产物的抗菌活性通过盘扩散和最小抑制浓度方法评估，对三种革兰氏阳性细菌、三种革兰氏阴性细菌、一种酵母和一种真菌菌株进行了测试。