5-acetyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidine-2(1H)-thione

• 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: 5-acetyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidine-2(1H)-thione
• 英文别名: 5-acetyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-thione；1-[6-methyl-4-(4-nitrophenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone
• 化学式: C₁₃H₁₃N₃O₃S
• 分子量: 291.331
• InChiKey: XLBZKYKEQZOEIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-5-氯甲基吡啶 、 5-acetyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidine-2(1H)-thione 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以65%的产率得到1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-methylthio)-4-methyl-6-(4-nitrophenyl)-1,6-dihydropyrimidin-5-yl]ethanone
  参考文献：
  名称：

  Convenient synthesis and biological activities of pyridine derivatives of 3,4-dihydropyrimidin-2(1H)-ones

  摘要：

  Abstract2‐Chloro‐5‐(chloromethyl)‐pyridine reacted with 3,4‐dihydropyrimidin‐2(1H)‐ones 1 to afford 1‐[6‐aryl‐1‐(6‐chloropyridin‐3‐yl‐methyl)‐2‐(6‐chloropyridin‐3‐yl‐methylthio)‐4‐methyl‐1,6‐dihydropyrimidin‐5‐yl] carboxylates or ethanones 2 in good yields. The structure of the target compounds 2 was confirmed by IR, 1H NMR, EI‐MS, and elemental analyses, and compound 2a was further characterized by single crystal X‐ray diffraction. The preliminary bioassay indicated that some of the title compounds possess moderate insecticidal and fungicidal activities. J. Heterocyclic Chem., (2011).

  DOI：

  10.1002/jhet.390
• 作为产物：
  描述：

  对硝基苯甲醛 、 硫脲 、 乙酰丙酮 在 Al₂O₃-SO₃H 作用下， 反应 0.03h， 以81%的产率得到5-acetyl-6-methyl-4-(4-nitrophenyl)-3,4-dihydropyrimidine-2(1H)-thione
  参考文献：
  名称：

  用氧化铝硫酸在无溶剂微波照射下有效合成多取代的 3,4-二氢嘧啶-2(1H)-酮/硫酮

  摘要：

  在无溶剂微波辐射条件下，在硫酸铝 (Al2O3-SO3H) 作为环境友好的多相可回收催化剂存在下，开发了一种新的高效合成多取代二氢嘧啶酮衍生物或其硫类似物的方法。产率高，反应时间短。

  DOI：

  10.1080/10426500802083182

文献信息

• Efficient and Green Microwave-Assisted Multicomponent Biginelli Reaction for the Synthesis of Dihydropyrimidinones Catalyzed by Heteropolyanion-Based Ionic Liquids Under Solvent-Free Conditions
  作者：Renzhong Fu、Yang Yang、Wenchen Lai、Yongfeng Ma、Zhikai Chen、Jian Zhou、Wen Chai、Quan Wang、Rongxin Yuan

  DOI：10.1080/00397911.2014.976346

  日期：2015.2.16

  Abstract An efficient and green route for the synthesis of dihydropyrimidinones via microwave-assisted Biginelli reaction catalyzed by 3 mol% of heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical reaction was found to be compatible with different structurally diverse substrates. Good to excellent yields, short reaction times, and operational simplicity

  摘要 报道了一种在无溶剂条件下，由 3 mol% 杂多阴离子基离子液体催化的微波辅助 Biginelli 反应合成二氢嘧啶酮的高效绿色路线。发现实际反应与不同结构不同的底物相容。从良好到出色的产量、较短的反应时间和操作简单性是该协议的主要亮点。此外，基于杂多阴离子的离子液体很容易在 Biginelli 反应中重复使用。图形概要
• Boehmite nanoparticle catalyst for the one-pot multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones under solvent-free conditions
  作者：Ali Keivanloo、Mahdi Mirzaee、Mohammad Bakherad、Atena Soozani

  DOI：10.1016/s1872-2067(12)60759-1

  日期：2014.3

  Abstract A simple, green, and efficient synthesis protocol for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones using boehmite nanoparticles as catalyst was developed. It did not use any toxic metal catalysts or corrosive acidic reagents. The method gave good to excellent yields and has short reaction time, operational simplicity, and a recyclable catalyst.

  摘要 开发了一种以勃姆石纳米粒子为催化剂合成 3,4-dihydropyrimidin-2-(1H)-one 的简单、绿色、高效的合成方案。它没有使用任何有毒金属催化剂或腐蚀性酸性试剂。该方法收率高，反应时间短，操作简单，催化剂可回收利用。
• Synthesis and Biological Activities of Novel Thiazole Derivatives of DHPMs via the N, S-dialkylation
  作者：Xiao-Fei Zhu、De-Qing Shi

  DOI：10.1080/10426500701841680

  日期：2008.7.4

  A series of novel 1-[6-aryl-1-(2-chlorothiazol-5-yl-methyl)-2-(2-chlorothiazol-5-yl -methylsulfanyl)-4-methyl-1,6-dihydropyrimidin-5-yl]carboxylates or ethanones 2 were synthesized via the N,S-dialkylation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) 1 using 2-chloro-5-(chloromethyl)thiazole as the alkylation reagent in one-pot reaction. The structures of the target compounds were confirmed by IR, 1H

  一系列新型1-[6-芳基-1-(2-氯噻唑-5-基-甲基)-2-(2-氯噻唑-5-基-甲基硫烷基)-4-甲基-1,6-二氢嘧啶-5 -yl]羧酸酯或乙酮 2 是通过 3,4-二氢嘧啶-2(1H)-酮 (DHPM) 1 的 N,S-二烷基化合成的，使用 2-氯-5-(氯甲基)噻唑作为烷基化试剂。 - 锅反应。目标化合物的结构通过 IR、1H NMR、EI-MS 和元素分析确认，在 2c 的情况下，通过单晶 X 射线衍射确认。初步生物测定表明标题化合物2具有中至弱的杀真菌和杀虫活性。
• An Efficient Synthesis of Multi-Substituted 3,4-Dihydropyrimidin-2(1H)-ones/thiones Under Solvent-Free Microwave Irradiation Using Alumina Sulfuric Acid
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1080/10426500802083182

  日期：2008.12.23

  A new and efficient method for the synthesis of multi-substituted dihydropyrimidinone derivatives or their sulfur analogs has been developed under solvent-free microwave irradiation conditions in the presence of alumina sulfuric acid (Al2O3-SO3H) as an environmentally friendly heterogeneous recyclable catalyst, in high yields and short reaction time.

  在无溶剂微波辐射条件下，在硫酸铝 (Al2O3-SO3H) 作为环境友好的多相可回收催化剂存在下，开发了一种新的高效合成多取代二氢嘧啶酮衍生物或其硫类似物的方法。产率高，反应时间短。
• Three Component Reaction: An Efficient Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones and Thiones Using Heterogeneous Catalyst
  作者：Vinod Tribhuvannathji Kamble、Dnyanoba Baburao Muley、Sandeep Tukaram Atkore、Sharad Digambarrao Dakore

  DOI：10.1002/cjoc.201090084

  日期：2010.1

  supported on silica gel (HBF4‐SiO2) catalyzes efficiently the three component condensation of an aldehyde, a 1,3‐dicarbonyl compound and urea or thiourea to afford the corresponding 3,4‐dihydropyrimidin‐ 2(1H)‐ones and thiones in high yields. The ambient conditions, fast reaction rates, and excellent product yields are the important characteristics of this reaction.

  负载在硅胶上的氟硼酸（HBF 4 -SiO 2）有效催化醛，1,3-二羰基化合物与尿素或硫脲的三组分缩合，从而提供相应的3,4-二氢嘧啶-2（1 H）-和高产的硫酮。环境条件，快速的反应速率和优异的产物收率是该反应的重要特征。