1-(4,4-difluoro-5-hydroxymethyltetrahydrothiophen-3-yl)-1H-pyrimidine-2,4-dione | 799257-40-2

• 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-(4,4-difluoro-5-hydroxymethyltetrahydrothiophen-3-yl)-1H-pyrimidine-2,4-dione
• CAS: 799257-40-2
• 化学式: C₉H₁₀F₂N₂O₃S
• 分子量: 264.253
• InChiKey: MHUQKJVQJPCQKL-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.09
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4,4-difluoro-5-hydroxymethyltetrahydrothiophen-3-yl)-1H-pyrimidine-2,4-dione 在 吡啶 、 4-二甲氨基吡啶 、 乙酸酐 、 三苯基氯硅烷 、 三乙胺 、 氨 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以42%的产率得到4-amino-1-(4,4-difluoro-5-hydroxymethyltetrahydrothiophen-3-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of New 2‘,3‘-Dideoxy-6‘,6‘-difluoro-3‘-thionucleoside from gem-Difluorohomoallyl Alcohol

  摘要：

  [GRAPHICS]2',3'-Dideoxy-6',6'-difluoro-3'-thionucleoside 1b, an analogue of 3Tc that has high biological activities against HIV and HBV, has been synthesized from gem-difluorohomoallyl alcohol 3 in an efficient way. The key intermediate 4-amino-3,3-difluorotetrahydrothiophen-2-ylmethyl benzoate 15 was prepared from 2,2-difluoro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol 3 in 11 steps. The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1.

  DOI：

  10.1021/ol048423j
• 作为产物：
  描述：

  benzoic acid 4-[3-(3ethoxyacryloyl)ureido]-3,3-difluorotetrahydrothiophen-2-ylmethyl ester 在 硫酸 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 生成 1-(4,4-difluoro-5-hydroxymethyltetrahydrothiophen-3-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of New 2‘,3‘-Dideoxy-6‘,6‘-difluoro-3‘-thionucleoside from gem-Difluorohomoallyl Alcohol

  摘要：

  [GRAPHICS]2',3'-Dideoxy-6',6'-difluoro-3'-thionucleoside 1b, an analogue of 3Tc that has high biological activities against HIV and HBV, has been synthesized from gem-difluorohomoallyl alcohol 3 in an efficient way. The key intermediate 4-amino-3,3-difluorotetrahydrothiophen-2-ylmethyl benzoate 15 was prepared from 2,2-difluoro-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol 3 in 11 steps. The construction of pyrimidine ring with the amino group of compound 15 gave the target compound 1.

  DOI：

  10.1021/ol048423j