5-(benzylideneamino)pyrimidine-2,4(1H,3H)-dione | 42485-25-6

• 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-(benzylideneamino)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-(benzylideneamino)-1H-pyrimidine-2,4-dione
• CAS: 42485-25-6
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: RUUVMJULUAAHOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(benzylideneamino)pyrimidine-2,4(1H,3H)-dione 在 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1,3-bis(4-methoxybenzyl)-5-[3-(4-chlorophenyl)-5-phenyl-1,2,4-oxadiazol-4(5H)-yl]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Aldimines of 5-aminouracil as reagents in 1,3-dipolar cycloaddition reaction

  摘要：

  The condensation of 5-aminouracil with aromatic aldehydes gave the appropriate C-arylimines, which were used in [2+3] cycloaddition with nitrile oxides derived from 4-substituted benzaldoximes. As a result of the dipolar cycloaddition reaction several hitherto unknown 5-(3,5-diphenyl-1,2,4-oxadiazol-4(5H)-yl)pyrimidine-2,4(1H,3H)-diones have been obtained in satisfactory yields.

  DOI：

  10.1007/s00706-011-0616-1
• 作为产物：
  描述：

  5-氨基尿嘧啶 、 苯甲醛 以 乙醇 为溶剂， 生成 5-(benzylideneamino)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Pyrimidine based highly sensitive fluorescent receptor for Al3+ showing dual signalling mechanism

  摘要：

  一种新的荧光探针（5-[(4-二乙基氨基-2-羟基-苄亚基)-氨基]-1H-嘧啶-2,4-二酮）（受体1）是通过5-氨基尿嘧啶与4-(二乙基氨基)水杨醛的席夫碱缩合反应合成的。受体1在二甲基亚砜（DMSO）和水中对Al3+具有高度选择性，即使在存在生物相关阳离子（如Na+、K+、Ca2+、Mg2+、Pb2+和几种过渡金属离子）的情况下也是如此。受体1的最低检测限为1.62×10-10M，在DMSO中浓度范围为1.75×10-9至3.3×10-8M时对Al3+呈线性响应。受体1是有史以来第一个能够以组合方式显示亚胺（CN

  DOI：

  10.1039/c0ob00171f

文献信息

• Screening for Potential Antimicrobial Activities of Some Cationic Uracil Biocides Against Wide-Spreading Bacterial Strains
  作者：Nabel A. Negm、Ismail A. Aiad、Salah M. Tawfik

  DOI：10.1007/s11743-010-1229-0

  日期：2010.10

  Schiff bases and their cationic derivatives were evaluated as novel biocides against different bacteria and fungi strains. The results showed that the biocidal activity of the synthesized Schiff bases was considerably increased by quaternization. The influence of the cationic surfactants as biocides was increased by increasing the hydrophobic chain length and the presence of the methoxy groups. The biocidal

  合成并使用元素分析，FTIR，1 H-NMR和13分析了八种含有Schiff碱物种的新型基于尿嘧啶的阳离子表面活性剂核磁共振波谱 基于界面张力测量值和水/辛醇系统中的分配系数值，确定了合成的席夫碱及其阳离子衍生物的表面活性。合成的席夫碱及其阳离子衍生物被评估为针对不同细菌和真菌菌株的新型杀菌剂。结果表明，通过季铵化作用，合成的席夫碱的杀生物活性大大提高。阳离子表面活性剂作为杀菌剂的影响通过增加疏水链的长度和甲氧基的存在而增加。通过增加水/辛醇系统中的分配系数，还提高了杀菌活性。讨论了不同化合物的结构和表面活性/杀菌活性。
• Pyrimidine based highly sensitive fluorescent receptor for Al3+ showing dual signalling mechanism
  作者：K. K. Upadhyay、Ajit Kumar

  DOI：10.1039/c0ob00171f

  日期：——

  A new fluorescent probe (5-[(4-diethylamino-2-hydroxy-benzylidene)-amino]-1H-pyrimidine-2, 4-dione) (Receptor1) has been synthesized by the Schiff base condensation of 5-aminouracil with 4-(diethylamino)salicylaldehyde. The receptor 1 exhibits high selectively for Al3+ in DMSO as well as in aqueous solution even in the presence of biologically relevant cations such as Na+, K+, Ca2+, Mg2+, Pb2+ and several transition metal ions. The lowest detection limit for the receptor 1 was found to be 1.62 × 10−10 M with its linear response towards Al3+ in the concentration range of 1.75 × 10−9 to 3.3 × 10−8 M in DMSO. Receptor 1 is the first ever example where a single molecular probe is able to show imine (CN) isomerization inhibition along with twisted intramolecular charge transfer (TICT) in combinatorial fashion.

  一种新的荧光探针（5-[(4-二乙基氨基-2-羟基-苄亚基)-氨基]-1H-嘧啶-2,4-二酮）（受体1）是通过5-氨基尿嘧啶与4-(二乙基氨基)水杨醛的席夫碱缩合反应合成的。受体1在二甲基亚砜（DMSO）和水中对Al3+具有高度选择性，即使在存在生物相关阳离子（如Na+、K+、Ca2+、Mg2+、Pb2+和几种过渡金属离子）的情况下也是如此。受体1的最低检测限为1.62×10-10M，在DMSO中浓度范围为1.75×10-9至3.3×10-8M时对Al3+呈线性响应。受体1是有史以来第一个能够以组合方式显示亚胺（CN
• Synthesis of phosphorylated carbamoyluracils
  作者：I. L. Kuz'menko、E. V. Vel'chinskaya、T. V. Zvolinskaya、L. S. Kulik

  DOI：10.1007/bf01170748

  日期：1995.7
• 5-Arylideneaminouracils: I. Synthesis and relations between physicochemical parameters and biological activity
  作者：V. I. Krutikov、A. V. Erkin

  DOI：10.1134/s107036320905020x

  日期：2009.5

  A number of 5-arylideneaminouracils were synthesized by condensation of 5-aminouracil with substituted aromatic aldehydes. Correlation analysis according to Hantzsch revealed strong effects of the lipophilicity parameter and hydration energy of these compounds on their biological activity.
• Aldimines of 5-aminouracil as reagents in 1,3-dipolar cycloaddition reaction
  作者：Dominika Jakubiec、Krzysztof Z. Walczak

  DOI：10.1007/s00706-011-0616-1

  日期：2011.11

  The condensation of 5-aminouracil with aromatic aldehydes gave the appropriate C-arylimines, which were used in [2+3] cycloaddition with nitrile oxides derived from 4-substituted benzaldoximes. As a result of the dipolar cycloaddition reaction several hitherto unknown 5-(3,5-diphenyl-1,2,4-oxadiazol-4(5H)-yl)pyrimidine-2,4(1H,3H)-diones have been obtained in satisfactory yields.