2,6-bis-(4-cyanophenyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 2,6-bis-(4-cyanophenyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester
• 英文别名: methyl 2,6-bis(4-cyanophenyl)-1,2,5,6-tetrahydro-1-phenyl-4-(phenylamino)pyridine-3-carboxylate；methyl (2S,6R)-4-anilino-2,6-bis(4-cyanophenyl)-1-phenyl-3,6-dihydro-2H-pyridine-5-carboxylate
• 化学式: C₃₃H₂₆N₄O₂
• 分子量: 510.595
• InChiKey: KBSMQIKDDUMBTP-XDFJSJKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 、 苯胺 、 4-氰基苯甲醛 在 溶剂黄146 作用下， 反应 0.66h， 以94%的产率得到2,6-bis-(4-cyanophenyl)-1-phenyl-4-phenylamino-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  室温下以乙酸为溶剂和催化剂的无金属、一锅法快速合成四氢吡啶

  摘要：

  摘要 在无金属催化剂的条件下，通过串联反应开发了乙酸促进的四氢吡啶一锅法合成。该协议的一些重要特点是原子经济性高、收率好、程序简单、无需昂贵的柱层析、反应时间更短、无金属和反应条件温和。目前的方法不仅为高度取代的四氢吡啶 (THP) 和完全取代的四氢吡啶 (FTHP) 提供了一种替代方法，收率中等至良好。来自乙酸的 H+ 离子极大地促进了 THP 形成的合理机制。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版本，获取以下免费补充资源：

  DOI：

  10.1080/00397911.2013.838266

文献信息

• Metal-Free, One-Pot, Rapid Synthesis of Tetrahydropyridines Using Acetic Acid as Solvent and Catalyst at Room Temperature
  作者：Umamahesh Balijapalli、Sathishkumar Munusamy、Karthikeyan Natesan Sundaramoorthy、Sathiyanarayanan Kulathu Iyer

  DOI：10.1080/00397911.2013.838266

  日期：2014.4.3

  alternative approach for not only highly substituted tetrahydropyridines (THPs) but also fully substituted tetrahydropyridines (FTHPs) in moderate to good yields. The plausible mechanism for the formation of THPs was greatly promoted by the H+ ion coming from acetic acid. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following

  摘要 在无金属催化剂的条件下，通过串联反应开发了乙酸促进的四氢吡啶一锅法合成。该协议的一些重要特点是原子经济性高、收率好、程序简单、无需昂贵的柱层析、反应时间更短、无金属和反应条件温和。目前的方法不仅为高度取代的四氢吡啶 (THP) 和完全取代的四氢吡啶 (FTHP) 提供了一种替代方法，收率中等至良好。来自乙酸的 H+ 离子极大地促进了 THP 形成的合理机制。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版本，获取以下免费补充资源：
• 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。
• First report of syn isomers in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid: factors influencing the syn–anti ratios
  作者：Chhanda Mukhopadhyay、Sunil Rana、Ray J. Butcher、Ann Marie Schmiedekamp

  DOI：10.1016/j.tetlet.2011.08.140

  日期：2011.11

  This is the first report of the formation of a syn-diastereoisomer in the diastereoselective synthesis of highly functionalized piperidines catalysed by wet picric acid via a one-pot, step-economic condensation of aromatic aldehydes, 1,3-dicarbonyl compounds and aromatic amines. DFT calculation shows that anti isomers are more stable compared to the syn. The syn-anti ratio of the products depends on the temperature and the nature of substitution on both the aromatic aldehydes and aromatic amines. Conditions for getting pure anti and pure syn compounds have been studied. (C) 2011 Elsevier Ltd. All rights reserved.
• B(C6F5)3 as versatile catalyst: an efficient and mild protocol for the one-pot synthesis of functionalized piperidines and 2-substituted benzimidazole derivatives
  作者：Santosh Kumar Prajapti、Atulya Nagarsenkar、Sravanthi Devi Guggilapu、Bathini Nagendra Babu

  DOI：10.1016/j.tetlet.2015.10.074

  日期：2015.12

  An efficient, mild and environmentally benign protocol has been developed for the diastereoselective one-pot synthesis of functionalized piperidines via tandem reactions of aromatic aldehydes, amines and acetoacetic esters in the presence of a catalytic amount of tris(pentafluorophenyl)borane. Furthermore, B(C6F5)3 was successfully used to catalyze the synthesis of benzimidazole and its derivatives

  在催化量的三（五氟苯基）硼烷的存在下，通过芳族醛，胺和乙酰乙酸酯的串联反应，已经开发了一种高效，温和且对环境有益的方案，用于非对映选择性一锅合成官能化哌啶。此外，B（C 6 F 5）3已成功用于催化苯并咪唑及其衍生物从各种醛和邻苯二胺的合成。另外，本方案的适用性扩展到苯并恶唑和苯并噻唑的合成。