[(1S,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyloxymethyl]-phosphonic acid diisopropyl ester | 144782-17-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: [(1S,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyloxymethyl]-phosphonic acid diisopropyl ester
• 英文别名: 1-[(1R,4S)-4-[di(propan-2-yloxy)phosphorylmethoxy]cyclopent-2-en-1-yl]-5-methylpyrimidine-2,4-dione
• CAS: 144782-17-2
• 化学式: C₁₇H₂₇N₂O₆P
• 分子量: 386.385
• InChiKey: GNMKCDSRKKNWDR-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(1S,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyloxymethyl]-phosphonic acid diisopropyl ester 在 palladium on activated charcoal 氢气 作用下， 以 异丙醇 为溶剂， 以99.7%的产率得到[(1R,3S)-3-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyloxymethyl]-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  Preparation of carbocyclic phosphonate nucleosides

  摘要：

  A versatile and high-yielding synthesis of racemic carbocyclic phosphonate nucleosides of adenine, hypoxanthine, guanine, cytosine, uracil, and thymine has been developed. These newly prepared compounds are isosteric (and isoelectronic) with (carbo)cyclic 2,3-dideoxy- and 2,3-dideoxy-2',3'-didehydronucleoside monophosphates.

  DOI：

  10.1016/s0040-4039(00)79086-1
• 作为产物：
  描述：

  在 盐酸 、 ammonium hydroxide 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 8.0h， 生成 [(1S,4R)-4-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyloxymethyl]-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  Preparation of carbocyclic phosphonate nucleosides

  摘要：

  A versatile and high-yielding synthesis of racemic carbocyclic phosphonate nucleosides of adenine, hypoxanthine, guanine, cytosine, uracil, and thymine has been developed. These newly prepared compounds are isosteric (and isoelectronic) with (carbo)cyclic 2,3-dideoxy- and 2,3-dideoxy-2',3'-didehydronucleoside monophosphates.

  DOI：

  10.1016/s0040-4039(00)79086-1