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

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-2-oxo-4-(3-hydroxy-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimidin-5-carboxylate；Ethyl 2-hydroxy-4-(3-hydroxy-4-methoxyphenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate；ethyl 4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₅H₁₈N₂O₅
• 分子量: 306.318
• InChiKey: KVBDYPHGAPGRSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异香兰素 、 乙酰乙酸乙酯 、 尿素 在 nickel nanoparticles (Ni NPs) 作用下， 反应 0.08h， 以87%的产率得到ethyl 4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction

  摘要：

  镍纳米颗粒（Ni NPs）在微波辐射下，能够在一锅法环缩合反应中表现出催化活性，用于从芳香族/杂芳香族/脂肪族醛、尿素/硫脲和乙基乙酰乙酸酯制备3,4-二氢嘧啶-2(1H)-酮，通过比吉内利反应已被描述。紫外吸收光谱显示出金属镍的特征，并且粒径通过透射电子显微镜（TEM）确定。反应结束后，Ni NPs可以重新回收并重复使用，且没有明显的活性损失。

  DOI：

  10.5012/bkcs.2010.31.02.351

文献信息

• Cu(OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones
  作者：A.S. Paraskar、G.K. Dewkar、A. Sudalai

  DOI：10.1016/s0040-4039(03)00619-1

  日期：2003.4

  Copper(II) triflate catalyzes efficiently the three-component condensation reaction of an aldehyde, β-ketoester and urea in acetonitrile to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones in high yields. The catalyst exhibited remarkable reusable activity.

  三氟甲磺酸铜（II）有效催化醛，β-酮酸酯和尿素在乙腈中的三组分缩合反应，从而以高收率提供相应的3,4-二氢嘧啶-2（1 H）-酮。该催化剂表现出显着的可重复使用的活性。
• Dihydropyrimidinones: efficient one-pot green synthesis using Montmorillonite-KSF and evaluation of their cytotoxic activity
  作者：Saleem Farooq、Fahad A. Alharthi、Ali Alsalme、Aashiq Hussain、Bashir A. Dar、Abid Hamid、S. Koul

  DOI：10.1039/d0ra09072g

  日期：——

  A simple, efficient, cost-effective, recyclable and green approach has been developed for the synthesis of new dihydropyrimidinone analogs via the Biginelli reaction. The methodology involves a multicomponent reaction catalyzed by “HPA-Montmorillonite-KSF” as a reusable and heterogeneous catalyst. This method gives an efficient and much improved modification of the original Biginelli reaction, in terms

  已经开发了一种简单、高效、经济、可回收和绿色的方法，用于通过Biginelli 反应合成新的二氢嘧啶酮类似物。该方法涉及由“HPA-蒙脱石-KSF”作为可重复使用的非均相催化剂催化的多组分反应。该方法在无溶剂条件下的产率和反应时间短方面对原始 Biginelli 反应进行了有效且大大改进的改进。所有衍生物都针对一组四种不同的人类癌细胞系进行细胞毒性筛选，即. 结肠 (Colo-205)、前列腺 (PC-3)、白血病 (THP-1) 和肺 (A549) 以检查它们对百分比增长的影响。MTT [3-(4,5-二甲基噻唑-基)-二苯基溴化四唑]细胞毒性试验用于检查IC 50值。在合成的类似物中，16a对肺 (A549)、白血病 (THP-1)、前列腺 (PC-3)和结肠（Colo-205）癌症系，分别。16a _通过克隆形成（集落形成）和划痕运动（伤口愈合）测定进一步检查了类似物对癌细胞特性的影响，从而发现它减少了肺癌细胞系
• Magnesium Chloride Hexahydrate Catalyzed One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2‐(1<i>H</i>)ones Under Solvent‐Free Conditions
  作者：Guo‐Lin Zhang、Xiao‐Hua Cai

  DOI：10.1081/scc-200050956

  日期：2005.3

  Abstract 3,4‐Dihydropyrimidin‐2‐(1H)‐one were prepared by Biginelli condensation of aldehyde, 1,3‐dicarbonyl compound and urea under solvent‐free condition at 80°C with magnesium chloride hexahydrate as catalyst.

  摘要 3,4-二氢嘧啶-2-(1H)-酮是由醛、1,3-二羰基化合物和尿素在80°C、无溶剂条件下以六水氯化镁为催化剂进行Biginelli缩合反应制备的。
• New Procedure for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1<i>H</i>)‐ones by Biginelli Reaction
  作者：Feng Xu、Jian‐Jun Wang、You‐Ping Tian

  DOI：10.1080/00397910701873524

  日期：2008.3.28

  Abstract A practical green chemistry procedure for synthesis of 3,4‐dihydropyrimidin‐2(1H);‐ones in good yields was successfully carried out in micellar systems according to the Biginelli reaction using β‐ketoester, urea and appropriate aromatic aldehyde in the presence of CuCl2 · H2O as catalyst. The advantages of this method involved the broader application scope of substrates, the more environmental

  摘要 根据 Biginelli 反应，在胶束体系中使用 β-酮酯、尿素和适当的芳香醛在胶束体系中成功地合成了 3,4-二氢嘧啶-2(1H);-ones 的实用绿色化学程序。 CuCl2·H2O作为催化剂。该方法的优点包括底物适用范围更广、工艺更环保、路易斯酸催化剂成本低。
• COMPARATIVE STUDIES OF LEWIS ACIDITY OF ALKYL-TIN CHLORIDES IN MULTICOMPONENT BIGINELLI CONDENSATION USING GRINDSTONE CHEMISTRY TECHNIQUE
  作者：HARSHITA SACHDEVA、REKHA SAROJ、SARITA KHATURIA、HAR LAL SINGH

  DOI：10.4067/s0717-97072012000100013

  日期：——

  A simple and efficient procedure for the one pot Biginelli Condensation Reaction of aldehydes, (beta-ketoester and urea employing SnCl4 center dot 5H(2)O /mono/di/tri-butyl-tin chloride as a novel catalyst is described. Compared to classical Biginelli reaction conditions, the present method has the advantages of good yields, short reaction times and experimental simplicity. Further, comparative efficiency of alkyl- tin chlorides in multicomponent Biginelli Condensation Reaction is also studied under solvent free conditions.