ethyl 6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate | 313970-38-6

• 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: ethyl 6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
• 英文别名: 5-carboethoxy-6-methyl-4-phenyl-3,4-dihydropyridin-2-one；2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester；2-Methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydro-pyridin-3-carbonsaeure-aethylester；Ethyl 2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylate；ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 313970-38-6
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: APYIVQOKMPJKFX-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• 沸点：
  447.3±45.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate 在 N,N-二甲基甲酰胺 、 三氯氧磷 、 水 、 sodium acetate 作用下， 反应 0.58h， 以62%的产率得到ethyl 6-chloro-4-phenyl-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Eco-Friendly Methodology to Prepare N-Heterocycles Related to Dihydropyridines: Microwave-Assisted Synthesis of Alkyl 4-Arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4-Arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H,3H)-dione

  摘要：

  本文描述了通过微波加速反应，高效合成烷基4-芳基取代-6-氯-5-甲酰基-2-甲基-1,4-二氢吡啶-3-羧酸酯和4-芳基取代-4,7-二氢-呋喃[3,4-b]吡啶-2,5(1H,3H)-二酮的方法。该环保合成途径不涉及传统加热中的苛刻或高度污染条件，减少了溶剂使用和回收，简化了后处理步骤，易于规模放大，能耗低，并且产率适中至较高。

  DOI：

  10.3390/molecules16119620
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium acetate 、 乙酸酐 作用下， 生成 ethyl 6-methyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
  参考文献：
  名称：

  Gohdes, Journal fur praktische Chemie (Leipzig 1954), 1929, vol. <2> 123, p. 172,177, 178, 180

  摘要：

  DOI：

文献信息

• Efficient sonochemical synthesis of alkyl 4-aryl-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate derivatives
  作者：Enrique Ruiz、Hortensia Rodríguez、Julieta Coro、Vladimir Niebla、Alfredo Rodríguez、Roberto Martínez-Alvarez、Hector Novoa de Armas、Margarita Suárez、Nazario Martín

  DOI：10.1016/j.ultsonch.2011.07.003

  日期：2012.3

  facile, efficient and environment-friendly protocol for the synthesis of 6-chloro-5-formyl-1,4-dihydropyridine derivatives has been developed by the convenient ultrasound-mediated reaction of 2(1H)pyridone derivatives with the Vilsmeier-Haack reagent. This method provides several advantages over current reaction methodologies including a simpler work-up procedure, shorter reaction times and higher yields

  通过2（1H）吡啶酮衍生物与Vilsmeier-Haack试剂的便捷超声介导反应，已开发出一种简便，高效且环境友好的合成6-氯-5-甲酰基-1,4-二氢吡啶衍生物的方案。 。与当前的反应方法相比，该方法具有多个优点，包括更简单的后处理步骤，更短的反应时间和更高的产率。
• Electron-transfer induced oxidation of 2-oxo-1,2,3,4-tetrahydropyridines using TiO2 anatase-nanoparticles: steric and electronic substitution effects
  作者：Hamid Reza Memarian、Mahdieh Kalantari

  DOI：10.1007/s13738-018-1407-y

  日期：2018.9

  The steric and electronic effects of 4-substitution in various 4-aryl substituted 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyridines were investigated by exposing them to the UV-light in the presence or absence of the TiO2 anatase-nanoparticles. The results clearly indicate the effective presence of the photo-catalyst and also the electron-donating effect of 4-aryl substitution on drastic decreasing of

  通过在存在或不存在TiO的情况下将其暴露于紫外光下，研究了4-取代在各种4-芳基取代的5-碳乙氧基-2-氧-1,2,3,4-四氢吡啶中的空间和电子效应2种锐钛矿型纳米粒子。结果清楚地表明光催化剂的有效存在，以及4-芳基取代的电子给体作用对辐照时间的急剧减少。DFT计算研究和循环伏安法测量结果支持了有关4取代基电子性质的实验结果。
• High-throughput preparation of alkyl 4-aryl substituted-2-methyl-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylates under microwave irradiation
  作者：Hortensia Rodríguez、Julieta Coro、Anabel Lam、Esperanza Salfrán、Javier Rodríguez-Salarichs、Margarita Suárez、Fernando Albericio、Nazario Martin

  DOI：10.3998/ark.5550190.0012.909

  日期：——

  An efficient high-throughput synthesis of 4-aryl substituted 1,4,5,6-tetrahydro-2-methyl-6thioxopyridine-3-carboxylates 5a-p was developed by using Lawesson’s reagent, a very effective thionating reagent for carbonyl compounds, under conventional conditions and microwave irradiation. In order to gain a better understanding of the structure of the heterocycles obtained, theoretical calculations at the

  4-芳基取代的 1,4,5,6-四氢-2-甲基-6thioxopyridine-3-carboxylates 5a-p 的高效高通量合成是通过使用 Lawesson 试剂开发的，劳森试剂是一种非常有效的羰基化合物硫代试剂，在常规条件和微波辐射。为了更好地理解所得杂环的结构，进行了从头算水平的理论计算。
• Steric and electronic substitution effects on the thermal oxidation of 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyridines
  作者：Hamid Reza Memarian、Mahdieh Kalantari

  DOI：10.1007/s13738-016-0966-z

  日期：2017.1

  by the hydroxyl radical formed in situ is occurred in the rate determining step, which is influenced by the steric and electronic effects of the substituted aryl group attached to this atom and also the stability of the radical intermediate involved in the oxidation reaction. The experimental results were supported by the computational studies.

  在乙腈水溶液中，过氧化二硫酸钾将各种4-芳基取代的5-羰基乙氧基-2-氧-1,2,3,4-四氢吡啶氧化为相应的4-芳基-5-羰基乙氧基-2-氧-1,2-二氢吡啶在热条件下。获得的产物具有良好至优异的产率。基于所提出的机理，在速率确定步骤中发生了通过原位形成的羟基从杂环的C 4原子中除去氢的过程，该过程受取代芳基的空间和电子效应的影响与该原子相连的基团，以及与氧化反应有关的自由基中间体的稳定性。实验结果得到了计算研究的支持。
• Synthesis of 6-styryldihydropyrimidinones and 6-styryldihydropyridinones via the respective 6-alkylphosphonates
  作者：Rufus Smits、Sergey Belyakov、Marina Petrova、Vladislav Kozhich、Ruslan Muhamadejev

  DOI：10.1007/s10593-023-03145-7

  日期：2022.12

  with 6-bromomethyl-3,4-dihydropyrimidin-2(1H)-one or analogous 6-bromomethyl-3,4-dihydropyridin-2(1H)-one provided the respective 6-alkylphosphonates in excellent yields. The heterocyclic alkylphosphonates are useful synthons in the Horner–Wadsworth–Emmons reaction for introducing a styryl moiety. Bromination of 6-methyl-4-phenyl-3,4-dihydropyridin-2(1H)-one with NBS in methanol resulted in an unexpected

  Arbuzov 反应中的亚磷酸三甲酯或三乙酯与 6-溴甲基-3,4-二氢嘧啶-2(1 H )-一或类似的 6-溴甲基-3,4-二氢吡啶-2(1 H )-一提供相应的 6-烷基膦酸盐以优异的收率。杂环烷基膦酸酯是 Horner-Wadsworth-Emmons 反应中用于引入苯乙烯基部分的有用合成子。在甲醇中用 NBS溴化 6-methyl-4-phenyl-3,4-dihydropyridin-2(1 H )-one 得到意想不到的化合物，而在氯仿中用溴溴化得到预期的 6-bromomethyl-3,4- dihydropyridin-2(1 H )-one，容易进行亲核取代。中间体和产物通过单晶X射线衍射验证。