5-Adamantan-1-yl-4-hydroxy-2-mercaptopyrimidin | 31935-14-5

• 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-Adamantan-1-yl-4-hydroxy-2-mercaptopyrimidin
• 英文别名: 5-adamantan-1-yl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one；5-(1-adamantyl)-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 31935-14-5
• 化学式: C₁₄H₁₈N₂OS
• 分子量: 262.376
• InChiKey: JEBULOJPSYCPRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Adamantan-1-yl-4-hydroxy-2-mercaptopyrimidin 在 氯乙酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 以83%的产率得到5-(1-adamantyl)uracil
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234
• 作为产物：
  描述：

  甲酸乙酯 、 2-(1-金刚烷基)乙酸甲酯 、 硫脲 在 lithium hexamethyldisilazane 作用下， 生成 5-Adamantan-1-yl-4-hydroxy-2-mercaptopyrimidin
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234