ethyl 2,6-bis(3-chlorophenyl)-1-(4-chlorophenyl)-4-(4-chlorophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-90-2

• 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-chlorophenyl)-4-(4-chlorophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• CAS: 1130969-90-2
• 化学式: C₃₂H₂₆Cl₄N₂O₂
• 分子量: 612.383
• InChiKey: KHKGNGUVXCJCJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.92
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对氯苯胺 、 3-氯苯甲醛 在 Iron(III) nitrate nonahydrate 作用下， 以 乙醇 为溶剂， 反应 6.5h， 以84%的产率得到ethyl 2,6-bis(3-chlorophenyl)-1-(4-chlorophenyl)-4-(4-chlorophenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Fe（NO3）3·9H2O单锅合成高官能化哌啶的高效催化剂

  摘要：

  Fe（NO 3）3 ·9H 2 O可作为一种有效的催化剂，用于在环境温度下由芳族醛，苯胺和b-酮酸酯在乙醇中一锅三组分合成高度官能化的哌啶。该程序包括一些重要方面，例如易于处理，无需柱色谱，简单易用的前体以及良好到高收率。

  DOI：

  10.1002/jccs.201200421

文献信息

• 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。
• 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。
• One-Pot Three-Component Synthesis of Highly Substituted Piperidines Using 1-Methyl-2-Oxopyrrolidinium Hydrogen Sulfate
  作者：Seyed Sajad Sajadikhah、Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Adel Beigbabaei、Mojtaba Lashkari

  DOI：10.3184/174751912x13395258340271

  日期：2012.8

  1-Methyl-2-oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO4]) is used as an ionic liquid catalyst for the one-pot three-component synthesis of highly substituted piperidines from aromatic aldehydes, anilines and β–ketoesters in refluxing ethanol. This homogeneous catalyst procedure has the advantages of easy work-up, no need for column chromatography, simple and readily available precursors, and good

  1-甲基-2-氧代吡咯烷硫酸氢盐 ([Hpyro][HSO4]) 用作离子液体催化剂，用于在回流乙醇中由芳香醛、苯胺和 β-酮酯一锅三组分合成高度取代的哌啶。这种均相催化剂程序具有后处理简单、无需柱色谱、前体简单易得、收率高的优点。
• Patil, Dayanand; Chandam, Dattatray; Mulik, Abhijeet, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 4, p. 545 - 550
  作者：Patil, Dayanand、Chandam, Dattatray、Mulik, Abhijeet、Patil, Prasad、Jagdale, Suryabala、Deshmukh, Madhukar

  DOI：——

  日期：——
• 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.