methyl 2,6-bis(3-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130970-09-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl 2,6-bis(3-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: Methyl2,6-bis(3-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 4-anilino-2,6-bis(3-nitrophenyl)-1-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130970-09-0
• 化学式: C₃₁H₂₆N₄O₆
• 分子量: 550.571
• InChiKey: JZTQQEFDYZBWAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  127.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 乙酰乙酸甲酯 、 苯胺 在 1-甲基吡咯烷-2-酮硫酸盐 作用下， 以 乙醇 为溶剂， 反应 14.5h， 以33%的产率得到methyl 2,6-bis(3-nitrophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  使用 1-甲基-2-氧代吡咯烷硫酸氢盐一锅三组分合成高度取代的哌啶

  摘要：

  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。

  DOI：

  10.3184/174751912x13395258340271

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。
• LaCl3·7H2O as an Efficient Catalyst for One-Pot Synthesis of Highly Functionalized Piperidines via Multi-component Organic Reactions
  作者：Balijapalli Umamahesh、Venkatesan Sathesh、Gunasekar Ramachandran、Munusamy Sathishkumar、Kulatu Sathiyanarayanan

  DOI：10.1007/s10562-012-0829-x

  日期：2012.7

  The three-component one-pot synthesis of highly functionalized piperidine derivatives was carried out by condensing 1,3-dicarbonyl compounds with aromatic aldehydes and aniline using a catalytic amount (10 mol%) of LaCl3·7H2O in methanol at room temperature. The main features of current protocol include easy work up, mild reaction conditions, good yields and high atom economy.Graphical Abstract

  在室温下，使用催化量（10 mol%）的 LaCl3·7H2O 在甲醇中将 1,3-二羰基化合物与芳香醛和苯胺缩合，进行三组分一锅法合成高度官能化的哌啶衍生物。当前方案的主要特点包括易于操作、反应条件温和、产率高和原子经济性高。图形摘要
• SULFAMIC ACID CATALYZED FIVE COMPONENT REACTION FOR EFFICIENT AND ONE-POT SYNTHESIS OF DENSELY FUNCTIONALIZED TETRAHYDROPYRIDINE SCAFFOLD
  作者：ANIKETP SARKATE、JAIPRAKASH N SANGSHETTI、NANASAHEB B DHARBALE、AJINKYA P SARKATE、DEVANAND B SHINDE

  DOI：10.4067/s0717-97072015000100012

  日期：——

  acid in One-pot assembling of aromatic aldehydes, aromatic amines and β-keto esters to afford densely functionalized tetrahydropyridines in 70-89% yield has been presented. The advantage of sulfamic acid against other catalysts in terms of yield has been studied. The effect of different solvents on reaction time and yield has also been studied. Easy work up and mild reaction condition are the advantages

  已经提出了氨基磺酸在芳族醛，芳族胺和β-酮酯的一锅组装中以70-89％的产率提供致密官能化的四氢吡啶的用途。研究了氨基磺酸相对于其他催化剂在产率方面的优势。还研究了不同溶剂对反应时间和产率的影响。该方法的优点是易于后处理，反应条件温和。
• Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes and anilines with β-ketoesters: facile and atom-economical access to chiral tetrahydropyridines
  作者：Xuejian Li、Yanyan Zhao、Haijun Qu、Zhenjun Mao、Xufeng Lin

  DOI：10.1039/c2cc38349g

  日期：——

  The first catalytic asymmetric pseudo five-component (AB(2)C(2) type) reaction is reported. A spirocyclic chiral phosphoric acid catalyzed one-pot multicomponent reaction of aromatic aldehydes, anilines and beta-ketoesters and afforded highly functionalized enantioenriched tetrahydropyridines with high levels of stereocontrol.

  报告了第一个催化不对称拟五组分（AB（2）C（2）型）反应。螺环手性磷酸催化芳族醛，苯胺和β-酮酸酯的一锅多组分反应，并提供高度官能化的对映体富集的四氢吡啶，具有高水平的立体控制。