methyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate | 1130969-86-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: methyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: methyl 1-(4-methoxyphenyl)-4-(4-methoxyphenylamino)-2,6-bis(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate；methyl 4-(4-methoxyanilino)-1-(4-methoxyphenyl)-2,6-dithiophen-2-yl-3,6-dihydro-2H-pyridine-5-carboxylate
• CAS: 1130969-86-6
• 化学式: C₂₉H₂₈N₂O₄S₂
• 分子量: 532.684
• InChiKey: LSSFVZDTEHZUEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 甲氧苯胺 、 乙酰乙酸甲酯 在 bis(1,3-dimethyl-2-imidazolidinone)hydrotribromide 作用下， 以 乙醇 为溶剂， 反应 24.5h， 以43%的产率得到methyl 1-(4-methoxyphenyl)-4-((4-methoxyphenyl)amino)-2,6-di(thiophen-2-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Bis(1,3-dimethylimidazolidinone) Hydrotribromide (DITB) Promoted Multicomponent Reaction for the Synthesis of Highly Functionalized Piperidines

  摘要：

  A convenient and efficient method has been developed for the synthesis of highly functionalized piperidines via three-component, one-pot domino reaction of beta-ketoesters, aromatic aldehydes, and anilines in the presence of catalytic amount of bis(1,3-dimethylimidazolidinone) hydrotribromide (DITB) in ethanol at room temperature.

  DOI：

  10.3987/com-20-14201

文献信息

• Catalytic Asymmetric Five-Component Tandem Reaction: Diastereo- and Enantioselective Synthesis of Densely Functionalized Tetrahydropyridines with Biological Importance
  作者：Feng Shi、Wei Tan、Ren-Yi Zhu、Gui-Juan Xing、Shu-Jiang Tu

  DOI：10.1002/adsc.201300001

  日期：2013.5.17

  aldehydes and anilines have been established in the presence of a chiral phosphoric acid, affording densely functionalized tetrahydropyridines with concomitant generation of five σ bonds and two stereogenic centers in high diastereo‐ and enantioselectivities (up to >99:1 dr, 95:5 er). In addition, the first isolation and preparation of a diene species as the key intermediate of the reaction has been

  在手性磷酸存在下建立了第一个β-酮酸酯，芳香族醛和苯胺的催化不对称五组分串联反应，提供了高官能度的四氢吡啶并伴随生成五个σ键和两个立体异构中心。和对映选择性（高达> 99：1 dr，95：5 er）。另外，已经成功地实现了作为反应的关键中间体的二烯物种的首次分离和制备，从而导致了通过与原位的进一步缩合而形成所需的四氢吡啶。生成的亚胺，在一定程度上支持了串联的[4 + 2]反应路径。该方案不仅代表了这种五组分串联反应的第一个对映体选择性实例，而且还提供了前所未有的途径来获得对映体富集的具有结构多样性的四氢吡啶，这在药物化学中具有巨大的潜力。
• 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.
• Bis(1,3-dimethylimidazolidinone) Hydrotribromide (DITB) Promoted Multicomponent Reaction for the Synthesis of Highly Functionalized Piperidines
  作者：Wei Zhang、Zhiqiang Hu、Shiqiang Yan、Shuwang He、Shuying Li

  DOI：10.3987/com-20-14201

  日期：——

  A convenient and efficient method has been developed for the synthesis of highly functionalized piperidines via three-component, one-pot domino reaction of beta-ketoesters, aromatic aldehydes, and anilines in the presence of catalytic amount of bis(1,3-dimethylimidazolidinone) hydrotribromide (DITB) in ethanol at room temperature.