5-aceto-6-methyl-4-ethyl-3,4-dihydropyrimidin-2-(1H)-One | 98841-37-3

• 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: 5-aceto-6-methyl-4-ethyl-3,4-dihydropyrimidin-2-(1H)-One
• 英文别名: 5-acetyl-4-ethyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-acetyl-4-ethyl-6-methyl-3,4-dihydro-1H-pyrimidin-2-one；5-Acetyl-4-aethyl-6-methyl-3,4-dihydro-1H-pyrimidin-2-on；2-Oxo-4-aethyl-5-acetyl-6-methyl-1.2.3.4-tetrahydro-pyrimidin；5-acetyl-4-ethyl-6-methyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 98841-37-3
• 化学式: C₉H₁₄N₂O₂
• 分子量: 182.222
• InChiKey: ZUQBXLPXZRXHEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-aceto-6-methyl-4-ethyl-3,4-dihydropyrimidin-2-(1H)-One 、 O-乙基羟胺 以 乙醇 为溶剂， 反应 24.0h， 以77.7%的产率得到5-(1-(ethoxyimino)ethyl)-4-ethyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Evaluation of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives as tyrosinase inhibitors

  摘要：

  A series of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 15 bearing a hydroxyethoxyl group at position-4 of phenyl ring exhibited most potent tyrosinase inhibitory activity with IC50 value of 0.56 mM. The inhibition mechanism analysis of compound 15 demonstrated that the inhibitory effect of the compound on the tyrosinase was irreversible. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.076
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以0.744 g的产率得到5-aceto-6-methyl-4-ethyl-3,4-dihydropyrimidin-2-(1H)-One
  参考文献：
  名称：

  A General Approach to 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) via α-(thio)ureidoalkylation of 1,3-diketones or β-oxoesters

  摘要：

  我们开发出了一种新的通用方法，可用于制备迄今为止难以获得的大量 4-未取代和 4-烷基取代的 5-酰基-1,2,3,4-四氢嘧啶-2-亚硫酰（一）。该方法基于各种 1,3-二酮或β-氧代酯的烯醇化物与容易获得的 N-[烷基（甲苯基）甲基]硫脲、N-（叠氮甲基）硫脲和 N-[烷基（甲苯基）甲基]脲反应，然后在 TsOH 催化下对中间体 4-羟基六氢嘧啶-2-硫酮（一）进行脱水，而不分离或分离后者。

  DOI：

  10.1007/s10593-023-03146-6

文献信息

• A Simple and Efficient One-pot Synthesis of 4-alkyl-3,4-dihydropyrimidin-2(1<i>H</i>)-ones
  作者：Maksim A. Kolosov、Olesia G. Kulyk、Dmitriy A. Beloborodov、Valeriy D. Orlov

  DOI：10.3184/174751913x13573126386313

  日期：2013.2

  4-Alkyl-3,4-dihydropyrimidin-2(1 H)-ones possess a number of important properties in comparison with their 4-aryl analogues. We show that these compounds can be synthesised by a simple one-pot reaction of urea or thiourea, different aliphatic aldehydes (from acetaldehyde to valeraldehyde) and various dicarbonyl compounds (ethyl acetoac-etate, pentane-2,4-dione, N-(4-chlorophenyl)-3-oxobutanamide, acetoacetaldehyde dimethylacetal) in refluxing DMF or HOAc without use of any catalyst. The methylation of 4-alkyl-5-C(O)R-3,4-dihydropyrimidin-2(1 H)-ones leads to 1-methyl derivatives.

  与 4-芳基类似物相比，4-烷基-3,4-二氢嘧啶-2(1 H)-酮具有许多重要特性。我们的研究表明，这些化合物可以通过尿素或硫脲、不同的脂肪族醛（从乙醛到戊醛）和各种二羰基化合物（乙酰乙酸乙酯、戊烷-2,4-二酮、N-(4-氯苯基)-3-氧代丁酰胺、乙酰乙醛二甲基乙醛）在回流的 DMF 或 HOAc 中进行简单的单锅反应合成，无需使用任何催化剂。4- 烷基-5-C(O)-R-3,4-二氢嘧啶-2(1H)-酮的甲基化反应会产生 1-甲基衍生物。
• One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Acidic Ionic Liquids Under Solvent-Free Conditions
  作者：Jianzhou Gui、Dan Liu、Chan Wang、Feng Lu、Jingzhao Lian、Heng Jiang、Zhaolin Sun

  DOI：10.1080/00397910902774042

  日期：2009.9.8

  Abstract The acidic ionic liquids were new catalysts for the one-pot Biginelli reaction coupling of aldehyde, 1,3-dicarbonyl compound, and urea to afford the corresponding dihydropyrimidinones in good yields under solvent-free conditions. The catalysts could be recycled and reused five times without a noticeable decrease in catalytic activity.

  摘要 酸性离子液体是一种新型催化剂，可用于醛、1,3-二羰基化合物和尿素的一锅Biginelli反应偶联，在无溶剂条件下以良好的收率得到相应的二氢嘧啶酮。催化剂可以循环使用五次，催化活性没有明显下降。
• Wang, Min; Jiang, Heng; Wang, Zhichang, Journal of Chemical Research, 2005, # 11, p. 691 - 693
  作者：Wang, Min、Jiang, Heng、Wang, Zhichang

  DOI：——

  日期：——
• Chi; Ling, Scientia Sinica (English Edition), 1957, vol. 6, p. 247,250
  作者：Chi、Ling

  DOI：——

  日期：——
• Evaluation of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives as tyrosinase inhibitors
  作者：Jinbing Liu、Fengyan Wu、Lingjuan Chen、Jianming Hu、Liangzhong Zhao、Changhong Chen、Liwang Peng

  DOI：10.1016/j.bmcl.2011.02.076

  日期：2011.4

  A series of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 15 bearing a hydroxyethoxyl group at position-4 of phenyl ring exhibited most potent tyrosinase inhibitory activity with IC50 value of 0.56 mM. The inhibition mechanism analysis of compound 15 demonstrated that the inhibitory effect of the compound on the tyrosinase was irreversible. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.