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

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 6-methyl-2-oxo-4-(3-phenoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: Ethyl 6-methyl-2-oxo-4-(3-phenoxyphenyl)-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 6-methyl-2-oxo-4-(3-phenoxyphenyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: SNLWXGOTOPMEIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 间苯氧基苯甲醛 、 尿素 在 氯化锆(IV) 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以96%的产率得到ethyl 6-methyl-2-oxo-4-(3-phenoxyphenyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  氯化锆催化一锅合成3,4-二氢嘧啶-2（1 H）-ones

  摘要：

  四氯化锆可有效地催化芳族醛，β-酮酸酯和尿素在回流的乙醇中的三组分缩合反应，从而以高收率提供相应的二氢嘧啶酮。

  DOI：

  10.1016/s0040-4039(02)00280-0

文献信息

• New environmentally friendly solvent free synthesis of dihydropyrimidinones catalysed by N-butyl-N,N-dimethyl-α-phenylethylammonium bromide
  作者：K. Rosi Reddy、Ch. Venkateshwar Reddy、M. Mahesh、P.V.K. Raju、V.V. Narayana Reddy

  DOI：10.1016/j.tetlet.2003.09.030

  日期：2003.10

  N-Butyl-N,N-dimethyl-α-phenylethylammonium bromide catalyzes efficiently the three component condensation reaction of an aromatic aldehyde, a β-keto ester and urea/thiourea under solvent free conditions at 100°C to afford the corresponding dihydropyrimidinone in high yield.

  N-丁基-N，N-二甲基-α-苯基乙基溴化铵可在无溶剂条件下于100°C下有效催化芳族醛，β-酮酸酯和脲/硫脲的三组分缩合反应，从而得到相应的二氢嘧啶酮屈服。
• One-Pot Synthesis of Dihydropyrimidinones Using Polyaniline-Bismoclite Complex. A Facile and Reusable Catalyst for the Biginelli Reaction
  作者：Srinivasan Palaniappan、Banda Gangadasu、Vaidya Jayathirtha Rao

  DOI：10.1055/s-2004-822925

  日期：——

  Polyaniline-bismoclite complex was used as an efficient catalyst for the three-component condensation reaction of an aldehyde, β-ketoester, and urea in ethanol to afford the dihydropyrimidinones in excellent yields. Furthermore, after completion of reaction the catalyst could be easily recovered and reused without affecting its activity.

  聚苯胺-铋矿物复合物被用作高效催化剂，在乙醇中催化醛、β-酮酯和尿素的三组分缩合反应，良好地生成了二氢嘧啶酮。此外，反应完成后，催化剂可以轻松回收并重复使用，而不影响其活性。
• 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。
• Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Ch.Venkateshwar Reddy、M Mahesh、P.V.K Raju、T.Ramesh Babu、V.V.Narayana Reddy

  DOI：10.1016/s0040-4039(02)00280-0

  日期：2002.4

  Zirconium tetrachloride catalyzes efficiently the three component condensation reaction of an aromatic aldehyde, a β-ketoester and urea in refluxing ethanol to afford the corresponding dihydropyrimidinone in high yield.

  四氯化锆可有效地催化芳族醛，β-酮酸酯和尿素在回流的乙醇中的三组分缩合反应，从而以高收率提供相应的二氢嘧啶酮。
• 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。