2-oxo-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester | 34906-28-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-oxo-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: ethyl 2-oxo-4,6-diphenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 2-oxo-4,6-diphenyl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 34906-28-0
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: YEDJESIABWTDMM-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C
• 沸点：
  486.8±45.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  2-oxo-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 劳森试剂 、 三氟化硼乙醚 、 甲烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙腈 、 苯 为溶剂， 反应 4.0h， 生成 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-diphenylpyrimidin-2-thione
  参考文献：
  名称：

  Synthesis of novel nucleosides and stereoselectivity of N-glycosidation

  摘要：

  An efficient synthetic route for novel nucleosides has been realized. We report the formation of alpha-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity observed. We also found that non-silylated pyrimidin-2(1H)-ones and pyrimidin-2(1H)-thiones having aromatic structures reacted with 1-fluororibose in the presence of a Lewis acid to give the corresponding nucleosides in good to high yield. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.017
• 作为产物：
  描述：

  phenyl [(phenyl)(tosyl)methyl]carbamate 在 ammonium hydroxide 、 sodium hydride 、 对甲苯磺酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 17.34h， 生成 2-oxo-4,6-diphenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  A new approach to the synthesis of Biginelli compounds

  摘要：

  A new synthesis of 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid esters is based on the reactions of alpha-tosyl-substituted phenyl carbamates with the enolates of beta-oxoesters followed by treatment with ammonia and dehydration of the resulting 4-hydroxyhexahydropyrimidin-2-ones.

  DOI：

  10.1070/mc2005v015n02abeh002022

文献信息

• First application of hexaaquaaluminium(III) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst in organic synthesis: a simple and efficient protocol for the multigram scale synthesis of 3,4-dihydropyrimidinones by Biginelli reaction
  作者：Mladen Litvić、Ivana Večenaj、Zrinka Mikuldaš Ladišić、Marija Lovrić、Vladimir Vinković、Mirela Filipan-Litvić

  DOI：10.1016/j.tet.2010.03.024

  日期：2010.5

  used as a mild acid catalyst in organic synthesis. A simple method of its preparation based on the reaction of aluminium triisopropoxide and tetrafluoroboric acid in isopropanol afforded catalyst of high purity and activity. The three-component Biginelli condensation of acetoacetate esters, urea and aldehydes catalyzed by 10 mol % of [Al(H2O)6](BF4)3 in refluxing acetonitrile afforded 3,4-dihydropyrimidonones

  首次将四氟硼酸六铝铝（III）用作有机合成中的弱酸催化剂。基于三异丙醇铝和四氟硼酸在异丙醇中反应的简单制备方法提供了高纯度和活性的催化剂。10 mol％的[Al（H 2 O）6 ]（BF 4）3催化的乙酰乙酸酯，脲和醛的三组分Biginelli缩合反应在回流的乙腈中，以克数为单位，以高至高收率得到3，4-二氢嘧啶酮。对酸敏感性反应物（例如噻吩基和呋喃基甲醛）的耐受性，对位阻β-酮酸酯的适用性以及在不损失催化活性的情况下简单的可回收性，使得该催化剂成为文献方法的良好替代品。该反应的机理包括形成所谓的“脲基-巴豆酸酯”而不是布朗斯台德型催化剂中发现的相应的酰基亚胺基中间体。
• Silica sulfuric acid: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Peyman Salehi、Minoo Dabiri、Mohammad Ali Zolfigol、Mohammad Ali Bodaghi Fard

  DOI：10.1016/s0040-4039(03)00436-2

  日期：2003.3

  Silica sulfuric acid efficiently catalyzes the three-component Biginelli reaction between an aldehyde, a β-dicarbonyl compound and urea or thiourea in refluxing ethanol to afford the corresponding dihydropyrimidinones in high yields. The catalyst is reusable and can be applied several times without any decrease in the yield of the reactions.

  二氧化硅硫酸在回流的乙醇中有效催化醛，β-二羰基化合物与脲或硫脲之间的三组分Biginelli反应，以高收率提供相应的二氢嘧啶酮。该催化剂是可重复使用的，并且可以多次使用而不会降低反应的产率。
• Synthesis of 3,4-dihydropyrimidin-2-ones (DHPMs) using mesoporous aluminosilicate (AlKIT-5) catalyst with cage type pore structure
  作者：D. Shobha、M.A. Chari、A. Mano、S.T. Selvan、K. Mukkanti、A. Vinu

  DOI：10.1016/j.tet.2009.10.074

  日期：2009.12

  Here we demonstrate on the synthesis of 3,4-dihydropyrimidin-2-ones (DHPMs) and their derivatives through a three-component condensation reactions of aldehyde, β-ketoester and urea or thiourea using mesoporous aluminosilicate (AlKIT-5) nanocage as catalyst and acetonitrile as solvent under reflux conditions. The catalyst was found to be highly active and selective, affording a high yield of DHPMs.

  在这里，我们证明了通过使用介孔铝硅酸盐（AlKIT-5）纳米笼作为催化剂，通过醛，β-酮酸酯与尿素或硫脲的三组分缩合反应，合成3,4-二氢嘧啶-2-酮（DHPM）及其衍生物在回流条件下用乙腈作为溶剂。发现该催化剂是高活性和选择性的，提供了高产率的DHPM。与经典的Biginelli反应条件相比，这种新方法始终具有高收率（80–96％）和较短的反应时间3.0–4.0 h的优势。研究了酸度和催化剂浓度对上述过程的影响。我们还演示了使用高活性AlKIT-5催化剂合成各种多功能Biginelli化合物的方法。
• A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF
  作者：Franca Bigi、Silvia Carloni、Bettina Frullanti、Raimondo Maggi、Giovanni Sartori

  DOI：10.1016/s0040-4039(99)00424-4

  日期：1999.4

  The reaction of aldehydes, β-dicarbonyl compounds and urea (Biginelli reaction) has been performed over solid acid catalysis, under solventless conditions or in water affording dihydropyrimidines in good yield and selectivity.

  醛，β-二羰基化合物与尿素的反应（Biginelli反应）已在固体酸催化下，无溶剂条件下或在水中进行，以良好的收率和选择性提供了二氢嘧啶。
• Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones over Silica Sulfuric Acid as a Reusable Catalyst under Solvent-free Conditions
  作者：Peyman Salehi、Minoo Dabiri、Mohammad Ali Zolfigol、Mohammad Ali Bodaghi Fard

  DOI：10.3987/com-03-9837

  日期：——

  3,4-Dihydropyrimidin-2(1H)-ones and their sulfur analogues are efficiently synthesized by the three-component condensation of β-dicarbonyl compounds, aromatic and aliphatic aldehydes, and urea or thiourea in the presence of catalytic amounts of silica sulfuric acid under solvent-free conditions in high yields. The catalyst is recyclable and can be used several times without any decrease in the products

  3,4-Dihydropyrimidin-2(1H)-ones 及其硫类似物是在催化量的二氧化硅硫酸存在下，通过 β-二羰基化合物、芳香醛和脂肪醛以及脲或硫脲的三组分缩合有效合成的在无溶剂条件下以高产率。该催化剂可循环使用，可多次使用，不会降低产品收率。