5-(4-chlorobenzylideneamino)pyrimidine-2,4(1H,3H)-dione | 42485-29-0

• 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-(4-chlorobenzylideneamino)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-[(4-chlorophenyl)methylideneamino]-1H-pyrimidine-2,4-dione
• CAS: 42485-29-0
• 化学式: C₁₁H₈ClN₃O₂
• 分子量: 249.656
• InChiKey: XBHOUNODMZZTMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 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-(4-chlorobenzylideneamino)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 14.5h， 生成 5-[3,5-bis(4-chlorophenyl)-1,2,4-oxadiazol-4(5H)-yl]-1,3-bis(4-methoxybenzyl)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 、 4-氯苯甲醛 在 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以93%的产率得到5-(4-chlorobenzylideneamino)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

文献信息

• 5-Aminouracil as a Building Block in Heterocyclic Synthesis, Part II. One-pot Synthesis of Pyrido[3,2-d:6,5-dʹ]dipyrimidines under Microwave Irradiation without Catalyst
  作者：Raafat M. Shaker、Mohamed A. Ameen、Afaf M. Abdel Hameed、Mohamed Abd Elrady

  DOI：10.1515/znb-2009-1013

  日期：2009.10.1

  An efficient and direct procedure for the synthesis of pyrido[3,2-d:6,5-dʹ]dipyrimidine derivatives under microwave-assisted conditions is been described. The structures of the products were characterized by elemental analyses, and their IR, 1H NMR, 13C NMR, and MS spectra. Graphical Abstract 5-Aminouracil as a Building Block in Heterocyclic Synthesis, Part II. One-pot Synthesis of Pyrido[3,2-d:6,5-dʹ]dipyrimidines

  描述了一种在微波辅助条件下合成吡啶并[3,2-d:6,5-d']二嘧啶衍生物的有效且直接的方法。产物的结构通过元素分析、IR、1H NMR、13C NMR和MS谱表征。图形摘要 5-氨基尿嘧啶作为杂环合成中的构建单元，第二部分。无催化剂微波辐照下吡啶并[3,2-d:6,5-dʹ]双嘧啶一锅法合成
• 5-Arylideneaminouracyls: IV. Phosphorylated derivatives and their biological activity
  作者：V. I. Krutikov、A. V. Erkin

  DOI：10.1134/s1070363209080106

  日期：2009.8

  It extension of the studies on the search for the new biologically active 5-aminouracyl derivatives, we synthesized by the reaction of dialkylphosphites with arylideneuracils respective aminomethylphosphonates. The high level of the antiviral and anti-mycobacterial activity of the target compounds correlates well with the physicochemical parameters characterizing their structure.
• 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.