1-<(2-acetoxyethoxy)methyl>barbituric acid | 154021-74-6

• 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: 1-<(2-acetoxyethoxy)methyl>barbituric acid
• 英文别名: 1-[(2-acetoxyethoxy)methyl]barbituric acid；2-[(2,4,6-trioxo-1,3-diazinan-1-yl)methoxy]ethyl acetate
• CAS: 154021-74-6
• 化学式: C₉H₁₂N₂O₆
• 分子量: 244.204
• InChiKey: GTLSZXVPIAVXIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<(2-acetoxyethoxy)methyl>barbituric acid 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 生成 1-(2-hydroxyethoxymethyl)-5-[(4-methylphenyl)methylidene]-1,3-diazinane-2,4,6-trione
  参考文献：
  名称：

  Azines and Azoles: CXX. Synthesis of Acyclic Analogs of N¹-Ribosides of Barbituric Acid and Its 5-ylidene Derivatives

  摘要：

  The reaction of 2,4,6-tris(trimethylsiloxy)pyrimidine with 2-oxabutane-1,4-diyl diacetate in methylene chloride in methylene chloride in the presence of SnCl4 proceeds regioselectively to form 1-[(2-acetoxyethoxy)methyl]barbituric acid. The latter is readily deacetylated to a free acyclic analog of N-ribosides of barbituric acid. 1[(2-Acetoxy- and 2-hydroxyethoxy)methyl]barbituric acids easily react with aromatic and heterocyclic aldehydes in water and organic solvents, forming 5-ylidenebarbituric acids. The structure of the products was proved by H-1 NMR and UV spectroscopy. Certain of the products exhibit a moderate antimicrobial and antiviral activity.

  DOI：

  10.1023/b:rugc.0000025513.88248.94
• 作为产物：
  描述：

  阿昔洛韦侧链 、 2,4,6-tris(trimethylsilyloxy)pyrimidine 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到1-<(2-acetoxyethoxy)methyl>barbituric acid
  参考文献：
  名称：

  Azines and Azoles: CXX. Synthesis of Acyclic Analogs of N¹-Ribosides of Barbituric Acid and Its 5-ylidene Derivatives

  摘要：

  The reaction of 2,4,6-tris(trimethylsiloxy)pyrimidine with 2-oxabutane-1,4-diyl diacetate in methylene chloride in methylene chloride in the presence of SnCl4 proceeds regioselectively to form 1-[(2-acetoxyethoxy)methyl]barbituric acid. The latter is readily deacetylated to a free acyclic analog of N-ribosides of barbituric acid. 1[(2-Acetoxy- and 2-hydroxyethoxy)methyl]barbituric acids easily react with aromatic and heterocyclic aldehydes in water and organic solvents, forming 5-ylidenebarbituric acids. The structure of the products was proved by H-1 NMR and UV spectroscopy. Certain of the products exhibit a moderate antimicrobial and antiviral activity.

  DOI：

  10.1023/b:rugc.0000025513.88248.94

文献信息

• Tzeng, Cherng-Chyi; Panzica, Raymond P.; Naguib, Fardos N.M., Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1399 - 1404
  作者：Tzeng, Cherng-Chyi、Panzica, Raymond P.、Naguib, Fardos N.M.、Kouni, Mahmoud H. el

  DOI：——

  日期：——
• Azines and Azoles: CXX. Synthesis of Acyclic Analogs of N¹-Ribosides of Barbituric Acid and Its 5-ylidene Derivatives
  作者：E. P. Studentsov、A. N. Kokhanovskii、M. B. Ganina、N. I. Nikolaeva、E. V. Fedorova、A. V. Moskvin、B. A. Ivin

  DOI：10.1023/b:rugc.0000025513.88248.94

  日期：2004.2

  The reaction of 2,4,6-tris(trimethylsiloxy)pyrimidine with 2-oxabutane-1,4-diyl diacetate in methylene chloride in methylene chloride in the presence of SnCl4 proceeds regioselectively to form 1-[(2-acetoxyethoxy)methyl]barbituric acid. The latter is readily deacetylated to a free acyclic analog of N-ribosides of barbituric acid. 1[(2-Acetoxy- and 2-hydroxyethoxy)methyl]barbituric acids easily react with aromatic and heterocyclic aldehydes in water and organic solvents, forming 5-ylidenebarbituric acids. The structure of the products was proved by H-1 NMR and UV spectroscopy. Certain of the products exhibit a moderate antimicrobial and antiviral activity.