ethyl 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 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 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4‐(2,4‐dichlorophenyl)‐6‐methyl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate；ethyl 4-(2,4-dichlorophenyl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate；4-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-(ethoxycarbonyl)-4-(2,4-dichlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；3,4-dihydro-5-ethoxycarbonyl-4-(2,4-dichlorophenyl)-6-methylpyrimidine-2(1H)-one；4-(2,4-dichlorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；ethyl 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₄H₁₄Cl₂N₂O₃
• 分子量: 329.183
• InChiKey: TZGBGBGJHQURTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 溴-1,4-二氧六环复合物 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  General and Green Synthesis of C-6 Sulfonylmethyl 4-Aryl-3,4-dihydropyrimidinones in Water

  摘要：

  A simple, inexpensive, and green reaction permitting the synthesis of new C-6 arylsulfonylmethyl 4-aryl-3,4-dihydropyrimidinones in water by S-alkylation of 6-bromomethyl 3,4-dihydropyrimidinones 2 with benzenesulfinic acid anions 3 is reported. The required 6-bromomethyldihydropyrimidone precursors 2 were readily prepared using an organic solid brominating reagent.

  DOI：

  10.1080/00397910802654682
• 作为产物：
  描述：

  1,1'-[(2,4-dichlorophenyl)methylene]diurea 、 乙酰乙酸乙酯 在 甘露醇 、 citric acid 、 尿素 作用下， 以 melt 为溶剂， 反应 15.0h， 生成 ethyl 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  10.33224/rrch.2019.64.7.05

  摘要：

  DOI：

  10.33224/rrch.2019.64.7.05

文献信息

• A New Biginelli Reaction Procedure Using Potassium Hydrogen Sulfate as the Promoter for an Efficient Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-one
  作者：Shujiang Tu、Fang Fang、Songlei Zhu、Tuanjie Li、Xiaojing Zhang、Qiya Zhuang

  DOI：10.1055/s-2004-815419

  日期：——

  conditions have been found to carry out the Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives. This synthesis was performed using potassium hydrogen sulfate as the promoter in glycol solution. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yields (85-99%) and short reaction time (0.5-2 h).

  已经发现简单和改进的条件可以进行 Biginelli 反应以合成 3,4-二氢嘧啶-2(1H)-one 衍生物。该合成是在乙二醇溶液中使用硫酸氢钾作为促进剂进行的。与经典的 Biginelli 反应条件相比，这种新方法具有收率高（85-99%）和反应时间短（0.5-2 h）的优点。
• A One-Pot Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones from Primary Alcohols Promoted by Bi(NO3)3·5H2O in Two Different Media: Organic Solvent and Ionic Liquid
  作者：Ahmad Reza Khosropour、Ahmad R. Khosropour、Mohammd M. Khodaei、Mojtaba Beygzadeh、Mahbubeh Jokar

  DOI：10.3987/com-04-10257

  日期：——

  A new, simple and efficient procedure for the one-pot conversion of alcohols instead of aldehydes to the corresponding 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with Bi(NO 3 ) 3 .5H 2 O as a commercially available, inexpensive, stable and non-toxic reagent in two media, acetonitrile (as an organic solvent) and tetrabutylammonium bromide (as an ionic liquid) is described. This one-pot oxidation-cyclocondensation

  一种新的、简单且有效的方法，用于将醇而不是醛一锅转化为相应的 3,4-二氢嘧啶-2(1H)-酮 (DHPM)，其中 Bi(NO 3 ) 3 .5H 2 O 作为商业应用描述了在乙腈（作为有机溶剂）和四丁基溴化铵（作为离子液体）这两种介质中可获得、廉价、稳定和无毒的试剂。这种一锅氧化-环缩合反应无需分离任何中间体（醛）即可进行，从而缩短了时间，节省了能源和原材料。另一方面，用这种新的一锅法处理伯醇产生的脱氢嘧啶酮的产率高于传统方法中的产率。
• Synthesis of tetrahydropyrimidino[4,3-a]isoquinolines via regiospecific N-alkylation-annulation of 4-aryldihydropyrimidinones
  作者：Jagjeet Singh、Nitu Mahajan、Rattan L. Sharma、Tej K. Razdan

  DOI：10.1002/jhet.768

  日期：2011.11

  4‐Aryldihydropyrimidinones were obtained in excellent yields via solid‐phase Biginelli reaction of arylaldehydes, β‐ketoester and urea, using bismuth nitrate, immobilized on Al2O3 as catalyst. Subsequently, the products were converted into corresponding tetrahydropyrimidino[4,3‐a]isoquinolines (69–73% yield) by one‐pot regiospecific N‐alkylation‐annulation reaction using sodium hydride and dimethylaminopyridine

  使用固定在Al 2 O 3上的硝酸铋，通过芳基醛，β-酮酸酯和尿素的固相Biginelli反应，以极高的收率获得了4-芳基二氢嘧啶酮。随后，通过氢化钠和二甲基氨基吡啶的一锅区域特异性N-烷基化环化反应，将产物转化为相应的四氢嘧啶并[4,3-α]异喹啉（69-73％产率）。J.杂环化​​学。（2011）。
• Highly convenient one-pot conversion of aryl acylals or aryl aldehyde bisulfites into dihydropyrimidones using BI(NO3)3⋅5H2O
  作者：Ahmad R. Khosropour、Mohammad M. Khodaei、Mojtaba Beygzadeh

  DOI：10.1002/hc.20352

  日期：2007.8

  A new, facile, and efficient one-pot deprotection–cyclocondensation method is presented for the Biginelli reaction from aryl acylals or aryl aldehyde bisulfites in the presence of catalytic amounts of Bi(NO3)3 ⋅ 5H2O under solvent-free conditions. In addition, high levels of chemoselectivity for this synthesis have been achieved. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:684–687, 2007; Published

  在无溶剂条件下，在催化量的 Bi(NO3)3 ⋅ 5H2O 存在下，芳酰基或芳醛亚硫酸氢盐的 Biginelli 反应，提出了一种新的、简便且有效的单锅脱保护-环缩聚方法。此外，该合成还实现了高水平的化学选择性。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:684–687, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20352
• EFFICIENT AND GREEN CATALYTIC SYNTHESIS OF DIHYDROPYRIMIDINONE (THIONE) DERIVATIVES USING COBALT NITRATE IN SOLVENT-FREE CONDITIONS
  作者：MASOUD NASR-ESFAHANI、MORTEZA MONTAZEROZOHORI、MARYAM AGHEL-MIRREZAEE、HASSAN KASHI

  DOI：10.4067/s0717-97072014000100015

  日期：——

  environmentally friendly reaction conditions. Keywords: Dihydropyrimidinone, Dihydropyrimidinthione, Cobalt(II)Nitrate, Solvent-free, One-pot synthesis INTRODUCTION Synthesis of 3,4-dihydropyrimidine-2(1H)-Ones (DHPMs) through one-pot reaction of aromatic aldehyde, urea and ethyl acetoacetate in acid ethanol solution was initiated by Biginelli in 1893 1 . These compounds occupied an important place in medicinal

  摘要在无溶剂条件下，使用Co（NO 3）2 .6H 2 O合成了一系列3,4-二氢嘧啶-2（1H）-一（硫酮）衍生物。在导致经济途径的化学反应过程中避免有机溶剂是有效的。该反应的特征在于高效，短反应时间，高收率，简单的实验程序，催化剂的可获得性和环境友好的反应条件。关键词：二氢嘧啶酮，二氢嘧啶硫酮，硝酸钴（II），无溶剂，一锅法合成引言通过芳族醛，尿素和乙基的一锅法反应合成3,4-二氢嘧啶-2（1H）-一（DHPM） Biginelli于1893年发起了在酸性乙醇溶液中的乙酰乙酸酯1。这些化合物在药物和合成有机化学中占有重要地位，主要是因为它们具有广泛的生物活性2。值得注意的是，monastrol（1）是唯一可阻止哺乳动物细胞中正常双极纺锤体组装的细胞可渗透分子，从而导致细胞周期停滞