2-oxo-4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester | 340-71-6

• 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: 2-oxo-4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
• 英文别名: ethyl 2-oxo-4-phenyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 2-oxo-4-phenyl-6-(trifluoromethyl)-1,2,3,4-tetrahydro-5-pyrimidine carboxylate；2-Oxo-4-phenyl-6-trifluormethyl-1,2,3,4-tetrahydro-pyrimidin-5-carbonsaeure-aethylester；2-Oxo-4-phenyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester；ethyl 2-oxo-4-phenyl-6-(trifluoromethyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 340-71-6
• 化学式: C₁₄H₁₃F₃N₂O₃
• 分子量: 314.264
• InChiKey: IUHUHWDXBQXVKV-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C
• 沸点：
  347.6±42.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 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：
  6

反应信息

• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 在 polyphosphate ester 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.0h， 生成 2-oxo-4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Polyphosphate Ester-Mediated Synthesis of Dihydropyrimidines. Improved Conditions for the Biginelli Reaction

  摘要：

  二氢嘧啶7通过醛、乙酰乙酸酯和脲在一锅法中使用聚磷酸酯介导的环缩合反应，以高产率制备。与传统的Biginelli反应条件相比，产率显著提高。

  DOI：

  10.1055/s-1998-1764

文献信息

• Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives
  作者：Anil Valeru、Zhi-Bin Luo、Imran Khan、Bin Liu、Bhavanarushi Sngepu、Narender Reddy Godumagadda、Yin Xu、Jimin Xie

  DOI：10.1080/00397911.2018.1490769

  日期：2018.9.2

  Abstract A series of novel 6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives were obtained in good yields from ethyl 4,4,4-trifluoro-3-oxobutanoate, urea, and aryl aldehyde via Biginelli multicomponent reaction. All the corresponding products 4a–4p were examined against four human cancer cell lines (A549, HepG2, COLO205 and DU145) and compounds 4e, 4i, and 4 m which showed

  摘要 以 4,4,4-三氟-3-氧代丁酸乙酯、脲和芳基醛为原料，以良好的收率获得了一系列新型 6-(三氟甲基)-1,2,3,4-四氢嘧啶-5-羧酸酯衍生物。 Biginelli 多组分反应。针对四种人类癌细胞系（A549、HepG2、COLO205 和 DU145）对所有相应的产物 4a-4p 进行了检查，并已鉴定出具有良好抗癌活性的化合物 4e、4i 和 4m。图形概要
• Revisit to the Biginelli reaction: a novel and recyclable bioglycerol-based sulfonic acid functionalized carbon catalyst for one-pot synthesis of substituted 3,4-dihydropyrimidin-2-(1H)-ones
  作者：Karnakar Konkala、Narayana Murthy Sabbavarapu、Ramesh Katla、Nageswar Yadavalli Venkata Durga、Vijai Kumar Reddy T、Prabhavathi Devi Bethala L.A.、Prasad Rachapudi B.N.

  DOI：10.1016/j.tetlet.2012.02.018

  日期：2012.4

  synthetic protocol has been developed for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones by using a novel bioglycerol-based sulfonic acid functionalized carbon catalyst, devoid of moisture sensitive metal catalysts and corrosive acidic reagents. The developed method has the advantages of good to excellent yields, short reaction times, operational simplicity, and a recyclable catalyst. The catalyst can be

  通过使用新型的基于生物甘油的磺酸官能化的碳催化剂，开发了一种简单高效的合成方案，用于合成3,4-二氢嘧啶-2-（1 H）-一，该方法缺少对水分敏感的金属催化剂和腐蚀性酸性试剂。所开发的方法具有良好至优异的产率，短的反应时间，操作简单和可回收的催化剂的优点。该催化剂可以通过简单的方法由廉价且容易获得的甘油制备，并且已显示出可回收和可重复使用多达四个循环而没有任何活性损失。
• One-step solvent-free synthesis of fluoroalkyl-substituted 4-hydroxy-2-oxo(thioxo)hexahydropyrimidines in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate
  作者：E. S. Putilova、N. A. Troitskii、S. G. Zlotin、O. G. Khudina、Ya. V. Burgart、V. I. Saloutin、O. N. Chupakhin

  DOI：10.1134/s1070428006090259

  日期：2006.9

  A convenient procedure has been developed for the synthesis of fluoroalkyl-substituted 6-aryl-4-hydroxy-2-oxo-(thioxo)hexahydropyrimidine derivatives by three-component condensation of fluorinated beta-dicarbonyl compounds with aromatic aldehydes and urea or thiourea in the absence of a solvent using 6 mol% of 1-butyl-3-methylimidazolium tetrafluoroborate as catalyst.
• Vijay; Ganapaty; Rao, A. Srinivas, Asian Journal of Chemistry, 2010, vol. 22, # 4, p. 2518 - 2528
  作者：Vijay、Ganapaty、Rao, A. Srinivas

  DOI：——

  日期：——
• One-pot synthesis of difluoromethyl-containing dihydropyrimidinones catalyzed by Yb(PFO)3 under solvent and dehydrating agent free conditions
  作者：Mingxi Wu、Jinlong Yu、Wenwen Zhao、Jingjing Wu、Song Cao

  DOI：10.1016/j.jfluchem.2010.12.010

  日期：2011.3

  The difluoromethyl-containing Biginelli dihydropyrimidinone derivatives were synthesized by a one-pot cyclocondensation of ethyl 4,4-difluoroacetoacetate, urea, and a variety of aldehydes in the presence of 5 mol% ytterbium perfluorooctanoate [Yb(PFO)(3)] under solvent and dehydrating agent free conditions. The comparison of reaction conditions and products was made among the different 1,3-dicarbonyl substrates (ethyl acetoacetate, ethyl 4,4-difluoroacetoacetate and ethyl 4,4,4-trifluoroacetoacetate) for the Biginelli reaction. (C) 2010 Elsevier B.V. All rights reserved.