5-Methyl-2-methylsulfanyl-4-trimethylsilanyloxy-pyrimidine | 173208-26-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-Methyl-2-methylsulfanyl-4-trimethylsilanyloxy-pyrimidine
• 英文别名: Trimethyl-(5-methyl-2-methylsulfanylpyrimidin-4-yl)oxysilane
• CAS: 173208-26-9
• 化学式: C₉H₁₆N₂OSSi
• 分子量: 228.39
• InChiKey: LJCMONLNHPIVER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Methyl-2-methylsulfanyl-4-trimethylsilanyloxy-pyrimidine 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of 3?-deoxy-3?-fluoro and -3?-amino nucleosides from 2-methylthiopyrimidin-4(1H)-ones

  摘要：

  Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-beta-D-erythro-pentofuranoside (3) as well as 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimodo-beta-D-erythro-pentofuranose (12) were condensed with silylated 2-methylthiopyridin-4(1H)-ones 2a, b in the presence of trimethylsilyl triflate as a catalyst to produce the corresponding nucleosides 5, 6, 13. In these reactions, an endocyclic cleavage of C-O in 3 took place; therefore, acyclic nucleosides 4a,b were also formed. All 3'-fluoro nucleosides were deprotected with NH3/MeOH; the 3'-phthalimido nucleosides were deprotected with methylamine in ethanol. The latter method resulted in a concomitant substitution reaction in the pyrimidine moiety with replacement of the methylthio group. The 2-methylthio analogue of 3'-deoxy-3'-fluorothylmidine showed moderate activity against HIV-1.

  DOI：

  10.1007/bf00807039
• 作为产物：
  描述：

  六甲基二硅氮烷 、 2-(甲基硫代)-5-甲基嘧啶-4(1H)-酮 在 硫酸氢铵 作用下， 反应 3.0h， 生成 5-Methyl-2-methylsulfanyl-4-trimethylsilanyloxy-pyrimidine
  参考文献：
  名称：

  Zahran, Magdy A.; Abdel-Megied, Ahmed E. -S.; Abdel-Rahman, Adel A. -H., Heterocycles, 1995, vol. 41, # 11, p. 2507 - 2518

  摘要：

  DOI：