1-(2,4-dimethoxybenzyl)urea | 296277-76-4

• 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: 1-(2,4-dimethoxybenzyl)urea
• 英文别名: 2,4-dimethoxybenzylurea；(2,4-dimethoxyphenyl)methylurea
• CAS: 296277-76-4
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: HNAHGDZAQREPAU-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  360.5±42.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxybenzyl)urea 在 四丁基溴化铵 、 sodium ethanolate 、 caesium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 乙酸酐 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.75h， 生成 6-amino-3-butyl-1-[2,4-dimethoxybenzyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
  参考文献：
  名称：

  Development of Covalent, Clickable Probes for Adenosine A₁ and A₃ Receptors

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c02169
• 作为产物：
  描述：

  potassium cyanate 、 2,4-二甲氧基苯甲胺 在 硫酸 作用下， 以 水 为溶剂， 反应 1.5h， 以96%的产率得到1-(2,4-dimethoxybenzyl)urea
  参考文献：
  名称：

  Development of Covalent, Clickable Probes for Adenosine A₁ and A₃ Receptors

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c02169

文献信息

• Enantioselective synthesis of hydantoins by chiral acid-catalysed condensation of glyoxals and ureas
  作者：Sushant Aryal、Christopher A. Hone、Matthew I. J. Polson、Daniel J. Foley

  DOI：10.1039/d3sc01656k

  日期：——

  Hydantoins are important scaffolds in natural products and pharmaceuticals, with only a few synthetic strategies available for their asymmetric preparation. We herein describe a single-step enantioselective synthesis of 5-monosubstituted hydantoins via condensation of glyoxals and ureas in the presence of a chiral phosphoric acid at room temperature. Products were formed in up to 99% yield and 98 : 2

  乙内酰脲是天然产物和药物中的重要支架，但只有少数合成策略可用于其不对称制备。我们在此描述了在手性磷酸存在下在室温下通过乙二醛和脲的缩合来一步对映选择性合成5-单取代乙内酰脲。产物的产率高达 99%，比率为 98:2。通过机械和动力学研究，包括时程1 H NMR 监测，我们发现该反应可能是通过烯醇型中间体的面选择性质子化进行的。
• [EN] ANTI VIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2010046780A3

  公开（公告）日：2011-01-13
• Synthesis of Unsymmetrical Diarylureas via Pd-Catalyzed C–N Cross-Coupling Reactions
  作者：Simon Breitler、Nathan J. Oldenhuis、Brett P. Fors、Stephen L. Buchwald

  DOI：10.1021/ol201210t

  日期：2011.6.17

  A facile synthesis of unsymmetrical N,N'-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.
• Discovery of 3,4-dihydropyrimidin-2(1H)-ones with inhibitory activity against HIV-1 replication
  作者：Junwon Kim、Changmin Park、Taedong Ok、Wonyoung So、Mina Jo、Minjung Seo、Youngmi Kim、Jeong-Hun Sohn、Youngsam Park、Moon Kyeong Ju、Junghwan Kim、Sung-Jun Han、Tae-Hee Kim、Jonathan Cechetto、Jiyoun Nam、Peter Sommer、Zaesung No

  DOI：10.1016/j.bmcl.2011.12.090

  日期：2012.3

  3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) were selected and derivatized through a HIV-1 replication assay based on GFP reporter cells. Compounds 14, 25, 31, and 36 exhibited significant inhibition of HIV-1 replication with a good safety profile. Chiral separation of each enantiomer by fractional crystallization showed that only the S enantiomer retained anti-HIV activity. Compound (S)-40, a novel and potent DHPM analog, could serve as an advanced lead for further development and the determination of the mechanism of action. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of the Main Metabolite in Human Blood of the A₁ Adenosine Receptor Ligand [¹⁸F]CPFPX
  作者：Marcus H. Holschbach、Dirk Bier、Walter Wutz、Sabine Willbold、Ray A. Olsson

  DOI：10.1021/ol900169f

  日期：2009.10.1

  In human blood, the PET radiotracer [F-18]CPFPX (1) is metabolized to numerous metabolites, one (M1) being the most prominent in plasma 30 min p.i. Because the mass of injected tracer is <= 5 nmol, concentrations in plasma are too low to analyze. Human liver microsomes generate main metabolites having HPLC retention times identical to those in plasma. HPLC-MS tentatively identified M1 as 2. Synthesis of 2 and identical HPLC-MS spectra of 2 and M1 confirmed that assignment.