1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide | 131490-72-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide
• 英文别名: 5-(Carbamothioylamino)-1-(1,3-dihydroxypropan-2-yloxymethyl)imidazole-4-carboxamide
• CAS: 131490-72-7
• 化学式: C₉H₁₅N₅O₄S
• 分子量: 289.315
• InChiKey: GSXBYXSMVPRLPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  720.0±70.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide 在 sodium hydroxide 、 copper(II) sulfate 作用下， 反应 1.0h， 以61%的产率得到更昔洛韦
  参考文献：
  名称：

  A simple and efficient synthesis of 9-substituted guanines. Cyclodesulfurization of 1-substituted 5-[(thiocarbamoyl)amino]imidazole-4-carboxamides under aqueous basic conditions

  摘要：

  5-Aminoimidazole-4-carboxamide (AICA) (1a) is 1-alkylated by an improved method. The resulting 5-amino-1-alkylimidazole-4-carboxamides (1b-i) are converted to the corresponding 1-alkyl-5-[(thiocarbamoyl)-amino]imidazole-4-carboxamides (3). These compounds are ring closed under alkaline conditions to 9-substituted guanines (5) in very high yields by treatment with heavy-metal salts in aqueous sodium hydroxide, or, in somewhat lower yields, by S-oxidation with hydrogen peroxide or sodium perborate in aqueous sodium hydroxide.

  DOI：

  10.1021/jo00006a033
• 作为产物：
  描述：

  5-amino-1-<<1,3-bis(benzyloxy)-2-propoxy>methyl>-1H-imidazole-4-carboxamide 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 80.0 ℃ 、1.01 MPa 条件下， 反应 29.0h， 生成 1-<(1,3-dihydroxy-2-propoxy)methyl>-5-<(thiocarbamoyl)amino>-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  A simple and efficient synthesis of 9-substituted guanines. Cyclodesulfurization of 1-substituted 5-[(thiocarbamoyl)amino]imidazole-4-carboxamides under aqueous basic conditions

  摘要：

  5-Aminoimidazole-4-carboxamide (AICA) (1a) is 1-alkylated by an improved method. The resulting 5-amino-1-alkylimidazole-4-carboxamides (1b-i) are converted to the corresponding 1-alkyl-5-[(thiocarbamoyl)-amino]imidazole-4-carboxamides (3). These compounds are ring closed under alkaline conditions to 9-substituted guanines (5) in very high yields by treatment with heavy-metal salts in aqueous sodium hydroxide, or, in somewhat lower yields, by S-oxidation with hydrogen peroxide or sodium perborate in aqueous sodium hydroxide.

  DOI：

  10.1021/jo00006a033

文献信息

• A simple and efficient synthesis of 9-substituted guanines. Cyclodesulfurization of 1-substituted 5-[(thiocarbamoyl)amino]imidazole-4-carboxamides under aqueous basic conditions
  作者：Boerge Alhede、Finn Priess Clausen、Joergen Juhl-Christensen、Klaus K. McCluskey、Herbert F. Preikschat

  DOI：10.1021/jo00006a033

  日期：1991.3

  5-Aminoimidazole-4-carboxamide (AICA) (1a) is 1-alkylated by an improved method. The resulting 5-amino-1-alkylimidazole-4-carboxamides (1b-i) are converted to the corresponding 1-alkyl-5-[(thiocarbamoyl)-amino]imidazole-4-carboxamides (3). These compounds are ring closed under alkaline conditions to 9-substituted guanines (5) in very high yields by treatment with heavy-metal salts in aqueous sodium hydroxide, or, in somewhat lower yields, by S-oxidation with hydrogen peroxide or sodium perborate in aqueous sodium hydroxide.