5,5-diethyl-4-iminobarbituric acid | 58042-95-8

• 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: 5,5-diethyl-4-iminobarbituric acid
• 英文别名: acide 5,5-diethyl-4-iminobarbiturique；6-amino-5,5-diethyl-5H-pyrimidine-2,4-dione；5,5-diethyl-6-amino-5H-pyrimidine-2,4-dione；5,5-Diaethyl-6-amino-5H-pyrimidin-2,4-dion；5,5-Diethyl-6-imino-1,3-diazinane-2,4-dione；5,5-diethyl-6-imino-1,3-diazinane-2,4-dione
• CAS: 58042-95-8
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: SSNMPSGFZBQHKA-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.04 M

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：
  0.62
• 拓扑面积：
  84.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-diethyl-4-iminobarbituric acid 在 乙醚 、 aluminium amalgam 、 水 作用下， 生成 5,5-diethyl-6-amino-dihydro-pyrimidine-2,4-dione
  参考文献：
  名称：

  DE609026

  摘要：

  公开号：
• 作为产物：
  描述：

  (2-ethyl-2-cyano-butyryl)-urea 在 sodium ethanolate 作用下， 生成 5,5-diethyl-4-iminobarbituric acid
  参考文献：
  名称：

  Conrad; Zart, Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 339

  摘要：

  DOI：
• 作为试剂：
  描述：

  聚合甲醛 、 2,4-二氯苯胺 在 5,5-diethyl-4-iminobarbituric acid 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以13%的产率得到9,9-diethyl-6,8-dioxo-3-(2,4-dichlorophenyl)-2,3,4,5,6,7,8,9-octahydropyrimido<3,4-a>-s-triazine
  参考文献：
  名称：

  Synthèse et étude de l'activité antimicrobienne de dérivés diversement chlorés du squelette 3-phényloctahydropyrimido[3,4-a]-s-triazine

  摘要：

  These compounds were synthesised, via a double Mannich reaction between 5,5-diethyl-4-iminobarbituric acid, formaldehyde and primary chlorophenylamines. The by-products of the reaction, 1,3,5-triarylhexahydro-s-triazines and monoamino-methylpyrimidinediones, were identified and their formation discussed. It was shown that the extracyclic nitrogen atom underwent the first aminomethylation and that the substitution of the intracyclic nitrogen atom, inducing ring closure, took place in a second step. All the compounds exhibited antimicrobial activities against bacteria and/or fungi and the derivative presenting a chlorine atom in the 3-position on the nucleus was as active as miconazole nitrate against T rubrum and E floccosum.

  DOI：

  10.1016/0223-5234(91)90215-9

文献信息

• 4-Iminobarbiturates: Tautomerism and electrochemical behavior in relation to N(3) substitution.
  作者：CHRISTOPHE GIRAUD、CLAIRE GUEUTIN、OLIVIER LAFONT、MICHEL GUERNET、MARCEL MIOCQUE

  DOI：10.1248/cpb.36.563

  日期：——

  Tautomerism of 4-iminobarbiturates depends upon the presence of a substituent on the N(3)atom. The ultraviolet, infrared, proton nuclear magnetic resonance, 13C-nuclear magnetic resonance and mass spectrum data show that 3-alkylated compounds present an imido system while 3-unalkylated ones are characterized by an amidinoketone system.The electrochemical bahavior of these two groups was studied by polarography, cyclic voltammetry and controlled potential electrolysis in dipolar aprotic solvents (dimethyl sulfoxide and hexamethyl phosphoric triamide), and was found to be related to the structure : the reduction of 3-substituted compounds is more difficult (about 0.2 V) than the reduction of 3-unalkylated products. The monoelectronic mechanism of this reduction was determied and confirmed by the electrochemically induced formation of an anion which can be alkylated using methyl iodide.

  4-iminobarbiturates 的同分异构体取决于 N(3)原子上是否存在取代基。紫外线、红外线、质子核磁共振、13C 核磁共振和质谱数据显示，3-烷基化化合物呈现亚氨基体系，而 3-非烷基化化合物则以脒基酮体系为特征。通过极谱法、循环伏安法和在双极性非丙烷溶剂（二甲亚砜和六甲基磷酰三酰胺）中的受控电位电解法研究了这两个基团的电化学行为，发现它们与结构有关：3-取代型化合物的还原比 3-非烷基化产物的还原更困难（约 0.2 V）。电化学诱导形成的阴离子可使用甲基碘进行烷基化，从而确定并证实了这种还原的单电子机制。
• Boothe; Wilson, Journal of the American Chemical Society, 1946, vol. 68, p. 449
  作者：Boothe、Wilson

  DOI：——

  日期：——
• Menager; Loire; Petrakian, Annales Pharmaceutiques Francaises, 1995, vol. 53, # 1, p. 29 - 37
  作者：Menager、Loire、Petrakian、Combet Farnoux、Delabos、Garnier、Lafont

  DOI：——

  日期：——
• Conrad, Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 312
  作者：Conrad

  DOI：——

  日期：——
• DE156385
  申请人：——

  公开号：——

  公开（公告）日：——