triethyl 2,6-dimethyl-1-(p-tolyl)-1,4-dihydropyridine-3,4,5-tricarboxylate | 1190383-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: triethyl 2,6-dimethyl-1-(p-tolyl)-1,4-dihydropyridine-3,4,5-tricarboxylate
• 英文别名: triethyl 1,4-dihydro-2,6-dimethyl-1-p-tolylpyridine-3,4,5-tricarboxylate；triethyl 2,6-dimethyl-1-p-tolyl-1,4-dihydropyridine-3,4,5-tricarboxylate；triethyl 2,6-dimethyl-1-(4-methylphenyl)-4H-pyridine-3,4,5-tricarboxylate
• CAS: 1190383-75-5
• 化学式: C₂₃H₂₉NO₆
• 分子量: 415.486
• InChiKey: SPCBTOVPCWORLD-UHFFFAOYSA-N

物化性质

• 沸点：
  511.2±50.0 °C(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(4-甲基苯基)氨基]乙酸乙酯 、 乙酰乙酸乙酯 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以70%的产率得到triethyl 2,6-dimethyl-1-(p-tolyl)-1,4-dihydropyridine-3,4,5-tricarboxylate
  参考文献：
  名称：

  铜催化好氧级联氧化偶联/环化反应制备1，4-二氢吡啶衍生物

  摘要：

  已经描述了一种有效的铜催化的级联环化反应，该反应使用分子氧作为末端氧化剂在N-芳基甘氨酸酯和1,3-二羰基化合物之间制备多取代的1,4-二氢吡啶。各种N-芳基甘氨酸酯1和1，3-二羰基化合物2能够顺利地进行级联反应，以令人满意的产率得到所需的产物3。级联反应具有良好的官能团耐受性和温和的反应条件的优点。在控制实验的基础上，还提出了一种可能的机制。

  DOI：

  10.1021/acs.joc.6b01736

文献信息

• Catalytic Oxidation of C(<i>sp</i>³)H Bonds Induced by a Radical Cation Salt: Construction of 1,4-Dihydropyridines Using a Fragment-Reassembly Strategy
  作者：Xiaodong Jia、Yaxin Wang、Fangfang Peng、Congde Huo、Liangling Yu、Jing Liu、Xicun Wang

  DOI：10.1002/adsc.201300810

  日期：2014.4.14

  A fragment‐reassembly strategy was applied to the construction of 1,4‐dihydropyridines and phosphorus‐substituted 1,4‐dihydropyridines under catalytic radical cation salt‐induced C(sp)3H functionalization of glycine derivatives. Mechanistic studies show that domino C(sp)3H bond oxidation and CN bond cleavage reactions are involved.

  甲片段重组的策略应用到的1,4-二氢吡啶和施工磷取代的下催化自由基阳离子盐诱导C（1,4-二氢吡啶SP）3  ħ甘氨酸衍生物的官能化。机理研究表明，多米诺C（SP）3  H键的氧化和C  N键裂解反应都参与。
• Copper-Catalyzed Aerobic Cascade Oxidative Coupling/Cyclization for the Construction of 1,4-Dihydropyridine Derivatives
  作者：Zhi-Qiang Zhu、Zong-Bo Xie、Zhang-Gao Le

  DOI：10.1021/acs.joc.6b01736

  日期：2016.10.7

  An efficient copper-catalyzed cascade cyclization reaction for the preparation of polysubstituted 1,4-dihydropyridines between N-arylglycine esters and 1,3-dicarbonyl compounds using molecular oxygen as the terminal oxidant has been described. Various N-arylglycine esters 1 and 1,3-dicarbonyl compounds 2 were able to undergo the cascade reaction smoothly to afford the desired products 3 in satisfactory

  已经描述了一种有效的铜催化的级联环化反应，该反应使用分子氧作为末端氧化剂在N-芳基甘氨酸酯和1,3-二羰基化合物之间制备多取代的1,4-二氢吡啶。各种N-芳基甘氨酸酯1和1，3-二羰基化合物2能够顺利地进行级联反应，以令人满意的产率得到所需的产物3。级联反应具有良好的官能团耐受性和温和的反应条件的优点。在控制实验的基础上，还提出了一种可能的机制。
• Synthesis of New 1, 4-Dihydropyridines by Addition-Rearrangement Process with Imine Derivatives and &amp;#946;-Ketoester as Starting Materials in Solvent-Free Conditions (SUPPORTING INFORMATION)
  作者：Xueming Chen、Xiaoguang Huang、Yunyun Chen、Feng He、Xingshu Li

  DOI：10.2174/157017809787893082

  日期：2009.4.1

  N-substituted 1,4-dihydropyridines bearing a carboxyl group at the 4-position were synthesized in solvent-free conditions with Cu2+ as the catalyst, imine and β-ketoester as starting materials. The possible mechanism which consists of addition-rearrangement process was proposed and examined by the reaction of isolated product of first addition to β- ketoester.

  以Cu2+为催化剂，亚胺和β-酮酯为原料，在无溶剂条件下合成了4位带有羧基的N-取代1,4-二氢吡啶。通过首次加成到β-酮酯的分离产物的反应，提出并检验了由加成-重排过程组成的可能机制。
• Multicomponent reactions leading to symmetric and asymmetric multi-substituted 1,4-dihydropyridines on montmorillonite
  作者：Yu-peng Liu、Jin-ming Liu、Xin Wang、Tie-ming Cheng、Run-tao Li

  DOI：10.1016/j.tet.2013.04.006

  日期：2013.6

  Highly functionalized multi-substituted symmetric and asymmetric 1,4-dihydropyridines were concisely synthesized in moderate to good yields via one-pot multicomponent reactions (MCRs) of beta-dicarbonyl compounds, aldehydes and amines at room temperature on montmorillonite. The merits of this method include the environmentally friendly reaction conditions, simple operation, broad substrate, satisfied yields and the reuse of the montmorillonite. (C) 2013 Elsevier Ltd. All rights reserved.
• Cascade cyclization of glycine derivatives with β-ketoesters for polysubstituted 1,4-dihydropyridines by visible light photoredox catalysis
  作者：Xiao Zhu、Zhi-Qiang Zhu、Dong Guo、Shan Liu、Jiu-Jian Ji、Juan Tang、En Yuan、Zong-Bo Xie、Zhang-Gao Le

  DOI：10.1016/j.tet.2020.131353

  日期：2020.8

  Visible light photocatalytic cascade cyclization reaction between glycine derivatives and β-ketoesters using Ir (ppy)3 as a catalyst and dicumyl peroxide (DCP) as an oxidant was described. A series of N-aryl glycine esters proceeded the cyclization smoothly with β-ketoesters at room temperature, affording the desired 1,4-dihydropyridines (1,4-DHPs) in satisfactory yields. A possible mechanism for the

  描述了使用Ir（ppy）3作为催化剂和过氧化二枯基（DCP）作为氧化剂的甘氨酸衍生物与β-酮酸酯之间的可见光光催化级联环化反应。一系列N-芳基甘氨酸酯与β-酮酸酯在室温下顺利进行环化反应，以令人满意的产率提供所需的1,4-二氢吡啶（1,4-DHPs）。还提出了可见光氧化还原催化级联环化反应的可能机理。该协议不仅为合成各种1,4-二氢吡啶提供了一种高效便捷的方法，而且还具有潜在的实用性来构建生物活性分子。