ethyl 6-methyl-2-oxo-4-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 123629-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 6-methyl-2-oxo-4-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl (E)-6-methyl-2-oxo-4-styryl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate；(E)-ethyl 6-methyl-2-oxo-4-styryl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-ethoxycarbonyl-4-[(E)-2-phenylethenyl]-6-methyl-3,4-dihydropyrimidin-2-one；ethyl (E)-6-methyl-2-oxo-4-styryl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-styrylpyrimidine-5-carboxylate；(E) 4-styryl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-(1H)-one；ethyl 6-methyl-2-oxo-4-[(E)-2-phenylethenyl]-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 123629-39-0
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: MFTFMXXRCSLQAZ-MDZDMXLPSA-N

物化性质

• 熔点：
  232-235 °C
• 沸点：
  418.6±45.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-2-oxo-4-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 copper barium chromium oxide catalyst 作用下， 150.0 ℃ 、19.61 MPa 条件下， 生成 5‑ethoxycarbonyl‑4‑(2‑phenylethyl)‑6‑methyl‑3,4‑dihydropyrimidin‑2(1H)‑one
  参考文献：
  名称：

  Hydrogenation of Cyclic Ureides under Elevated Temperatures and Pressures. I.¹ 2-Keto-1,2,3,4-tetrahydropyrimidines

  摘要：

  DOI：

  10.1021/ja01320a058
• 作为产物：
  描述：

  肉桂醛 生成 ethyl 6-methyl-2-oxo-4-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Biginelli, Chemische Berichte, 1891, vol. 24, p. 2965

  摘要：

  DOI：

文献信息

• One-pot synthesis of 3,4-dihydropyrimidin-2(1<i>H</i>)-ones, thiones and 2-selenoxo DHPMs using 1-butyl-3-methylimidazolium hydrogen sulfate as non-halogenated ionic liquid
  作者：Behzad Mohammadi、Farahnaz K. Behbahani、Gholam B. Marandi、Behrouz Mirza

  DOI：10.1080/10426507.2020.1800702

  日期：2021.1.2

  1-Butyl-3-methylimidazolium hydrogen sulfate ([BMIM][HSO4]) as a non-halogenated ionic liquid (IL) was used for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones or 2-selenoxo DHPMs in a Biginelli type multi-component reaction. By using this ionic liquid, the reaction time was significantly reduced and the products were obtained in good to high yields. Also, in this method, the synthesis of novel 2-selenoxo

  摘要 1-丁基-3-甲基咪唑硫酸氢盐 ([BMIM][HSO4]) 作为非卤化离子液体 (IL) 用于合成 3,4-二氢嘧啶-2(1H)-酮和硫酮或 2 - 在 Biginelli 型多组分反应中的 selenoxo DHPM。通过使用该离子液体，反应时间显着缩短，并且以良好至高产率获得产物。此外，在该方法中，在这种离子液体的存在下引入了新型 2-硒代 DHPM 的合成，并通过 1H 和 13C NMR、FT-IR 和元素分析确定了它们的结构。图形概要
• NbCl₅-catalyzed Rapid and Efficient Synthesis of 3,4-Dihydropyrimidinones Under Ambient Conditions
  作者：J. S. Yadav、B. V. S. Reddy、Jaishri J. Naidu、K. Sadashiv

  DOI：10.1246/cl.2004.926

  日期：2004.7

  Three-component condensation of an aldehyde, 1,3-dicarbonyl compound and urea or thiourea proceeds smoothly at room temperature in the presence of 5 mol % of NbCl5 under extremely mild conditions to afford the corresponding 3,4-dihydropyrimidines in high to quantitative yields. This method is very useful for the synthesis of a wide range of dipyrimidinones at room temperature from aromatic, heterocyclic, and aliphatic aldehydes.

  在极温和的条件下，5摩尔％NbCl5的存在下，醛、1,3-二羰基化合物和脲或硫脲的三组分缩合在室温下顺利进行，获得相应的3,4-二氢嘧啶，在高至定量的产率下。这种方法非常适用于从芳香、杂环和脂肪醛室温合成广泛范围的双嘧啶酮。
• Silica-supported ZnCl₂ — A highly active and reusable heterogeneous catalyst for the one-pot synthesis of dihydropyrimidinones–thiones
  作者：Raman Gupta、Monika Gupta、Satya Paul、Rajive Gupta

  DOI：10.1139/v07-018

  日期：2007.3.1

  chloride catalyst was prepared and investigated for the Biginelli reaction. The key features of the catalyst include rapid reaction with 100% conversion of aldehyde, good catalyst recyclability, and high stability under the reaction conditions (passes hot filtration test successfully). A low catalyst loading (12 mol% of ZnCl2) was required to achieve a quantitative reaction. Other catalysts such as

  制备了一种新型二氧化硅负载的氯化锌催化剂并研究了 Biginelli 反应。该催化剂的主要特点是反应速度快，醛转化率100%，催化剂可回收性好，反应条件下稳定性高（成功通过热过滤试验）。实现定量反应需要低催化剂负载量（12 mol% 的 ZnCl2）。还制备了其他催化剂，如 SiO2-AlCl2、SiO2-AlCl2-ZnCl2，并与 SiO2-ZnCl2 的 Biginelli 反应活性进行了比较。关键词：硅胶，氯化锌，Biginelli 化合物，多相催化，可重复使用。
• Nickel Chloride Hexahydrate Catalyzed Multicomponent Biginelli's Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-Ones and Thiones
  作者：Şirin Gülten

  DOI：10.1002/jhet.2700

  日期：2017.3

  An efficient protocol is reported for the one‐pot three‐component Bignelli synthesis of a series of 3,4‐dihydropyrimidine‐2(1H)‐ones and thiones in good yields (66–90%) from the aldehydes (4‐benzyloxybenzaldehyde, 5‐bromovanilin, 4‐formyl‐1‐cyclohexene, and trans‐cinnamaldehyde), β‐keto esters (ethyl acetoacetate, allyl acetoacetate, and t‐butyl acetoacetate), and urea/thiourea in ethanol, using nickel

  据报道，从醛类（4-苄氧基苯甲醛）可以以良好的收率（66-90％）生成一系列3,4-二氢嘧啶-2（1 H）-酮和硫酮的单锅三组分Bignelli合成有效方法，使用六水合氯化镍作为乙醇，将乙醇中的5-溴movanilin，4-甲酰基-1-环己烯和反式肉桂醛，β-酮酸酯（乙酰乙酸乙酯，乙酰乙酸烯丙酯和叔丁基乙酰乙酸酯）和脲/硫脲催化剂。
• LiClO4-Catalyzed One-Pot Synthesis of Dihydropyrimidinones: An Improved Protocol for Biginelli Reaction
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、R. Srinivas、C. Venugopal、T. Ramalingam

  DOI：10.1055/s-2001-15229

  日期：——

  perchlorate efficiently catalyzes the three-component condensation reaction of aldehyde, β-keto ester and urea in refluxing acetonitrile to afford the corresponding dihydropyrimidinones in high yields under neutral conditions. LiOTf is also found to be an efficient catalyst for the synthesis of dihydropyrimidinones from aldehyde, β-keto ester and urea.

  高氯酸锂在中性条件下高效催化醛、β-酮酯和脲在回流乙腈中的三组分缩合反应，以高收率得到相应的二氢嘧啶酮。LiOTf 还被发现是从醛、β-酮酯和尿素合成二氢嘧啶酮的有效催化剂。