1-(1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridin-3-yl)ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridin-3-yl)ethanone
• 英文别名: 1-(1-benzyl-2-methyl-4-phenyl-4H-pyridin-3-yl)ethanone
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: FQGZKEQMYKFAMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(4-Nitrophenyl)methylideneamino]chromen-2-one 、 1-(1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridin-3-yl)ethanone 在 ytterbium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以0.454 g的产率得到3-acetyl-1-benzyl-2-methyl-5-(4-nitrophenyl)-4-phenyl-1,4,4a,5,6,12c-hexahydro-7H-chromeno[3,4-h][1,6]naphthyridin-7-one
  参考文献：
  名称：

  Exploration of C5–C6-Unsubstituted 1,4-Dihydropyridines for the Construction of exo-Hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylates Using a Stereoselective Povarov Reaction

  摘要：

  A wide variety of substituted exo-hexahydro-1H-chromeno[3,4-h][1,6]naphthyridine-3-carboxylate derivatives have been synthesized from 3-aminocoumarins, aldehydes, and 5,6-unsubstituted 1,4-dihydropyridine derivatives in the presence of 10 mol% of ytterbium(III) triflate in acetonitrile at room temperature using a one-pot Povarov reaction. Some of the salient features of this protocol are: good yields and no need for an aqueous workup procedure or chromatographic separation.

  DOI：

  10.1055/s-0034-1380431
• 作为产物：
  描述：

  反式肉桂醛 、 (Z)-4-(benzylamino)-3-penten-2-one 在 magnesium(II) perchlorate 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 70.0h， 以32%的产率得到1-(1-benzyl-2-methyl-4-phenyl-1,4-dihydropyridin-3-yl)ethanone
  参考文献：
  名称：

  Magnesium Perchlorate as Efficient Lewis Acid: A Simple and Convenient Route to 1,4-Dihydropyridines

  摘要：

  本文提出了一种新的合成多种1,2,3,4-四取代-1,4-二氢吡啶的协议，该协议基于Mg(ClO4)2的促进作用，用于从烯胺或羰基衍生物进行合成。

  DOI：

  10.1055/s-2007-990839

文献信息

• Lewis Acid-Catalyzed Sequential Transformations: Straightforward Preparation of Functional Dihydropyridines
  作者：Ramandeep Kaur Vohra、Christian Bruneau、Jean-Luc Renaud

  DOI：10.1002/adsc.200600343

  日期：2006.12

  Lewis acids catalyze the addition of β-enaminoacrylates or β-enaminones to α,β-unsaturated aldehydes leading to substituted dihydropyridines in high yields under mild reaction conditions.

  路易斯酸催化在温和的反应条件下，以高收率将β-烯胺丙烯酸酯或β-烯胺酮添加到α，β-不饱和醛中，从而生成取代的二氢吡啶。
• Convenient Synthesis of <i>N</i>-Benzyl-1,4-dihydropyridines, Cyclohexenones, and Bicyclo[3.3.1]nonan-3-one Derivatives from 1-Aza-1,3-butadienes
  作者：Jon K. F. Geirsson、Jonina F. Johannesdottir

  DOI：10.1021/jo960942f

  日期：1996.1.1

  Readily available 1-aza-1,3-butadienes (enimines) react with methyl acetoacetate and acetylacetone in the presence of catalytic amounts of lithium iodide to form in high yields unsymmetrically substituted 1,4-dihydropyridines or cyclohexenones. The reaction pathway depends on the structure of the enimine used. This divergence was not observed when the enimines were reacted with dimethyl 1,3-acetonedicarboxylate

  在催化量的碘化锂存在下，易于获得的1-氮杂-1,3-丁二烯（亚胺）与乙酰乙酸甲酯和乙酰丙酮反应，以高收率形成不对称取代的1,4-二氢吡啶或环己酮。反应途径取决于所用亚胺的结构。当亚胺与1，3-丙酮二羧酸二甲酯反应以明显的立体选择性反应以优异的产率提供双环[3.3.1]壬烷-3-酮衍生物时，未观察到这种差异。
• The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition
  作者：Xiu-Yu Chen、Hui Zheng、Ying Han、Jing Sun、Chao-Guo Yan

  DOI：10.3762/bjoc.19.73

  日期：——

  4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines in good yields and with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition reaction of dialkyl acetylenedicarboxylates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products and 1,3a

  摘要 异喹啉、乙炔二甲酸二烷基酯和 5,6-未取代的 1,4-二氢吡啶在乙腈中于室温下进行三组分反应，以良好的收率和高非对映选择性提供了官能化的异喹啉代[1,2- f ][1,6]萘啶。更重要的是，乙炔二甲酸二烷基酯和5,6-未取代的1,4-二氢吡啶在回流乙腈中发生正式的[2 + 2]环加成反应，得到了独特的2-氮杂双环[4.2.0]辛-3,7-二烯作为主要产物， 1,3a,4,6a-四氢环戊[ b ]吡咯通过进一步重排作为次要产物。 贝尔斯坦 J. 组织。化学。 2023, 19, 982–990。doi:10.3762/bjoc.19.73
• Reactions of 1-Aza-1,3-butadienes. An Expedient Synthesis of Unsymmetrically Substituted N-Benzyl-1,4-dihydropyridines and N-Benzyl-1,4-dihydronicotinamides.
  作者：Jon K. F. Giersson、Jonina F. Johannesdóttir、Johannes Reynisson、Juhani Huuskonen、Kari Rissanen、Wenjun Shi、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0348

  日期：——
• Hydrated ferric sulfate catalyzed synthesis of 5,6-unsubstituted 1,4-dihydropyridines using three-component reaction
  作者：Kobirul Islam、Deb K. Das、Abu T. Khan

  DOI：10.1016/j.tetlet.2014.08.067

  日期：2014.10

  A wide variety of 5,6-unsubstituted 1,4-dihydropyridines derivatives (4a-q) were synthesized through a one-pot three-component reaction from alpha,beta-unsaturated aldehydes, amines, and 1,3-diketones at room temperature using hydrated ferric sulfate as a Lewis acid catalyst. The key features of the present protocol are mild and simple reaction procedure, good to excellent yields, and use of inexpensive, recyclable, and environmentally benign catalyst. (C) 2014 Elsevier Ltd. All rights reserved.