diethyl ({2-[(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl}(difluoro)methyl)phosphonate | 1220514-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl ({2-[(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl}(difluoro)methyl)phosphonate
• CAS: 1220514-37-3
• 化学式: C₂₃H₂₇F₂N₂O₆P
• 分子量: 496.448
• InChiKey: MEKUJQNTJAUKQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.6
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl ({2-[(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl}(difluoro)methyl)phosphonate 在 氨 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以53 mg的产率得到diethyl ({2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl}(difluoro)methyl)phosphonate
  参考文献：
  名称：

  在N（1）上具有1- [膦基（甲基/二氟甲基）]-1,2-不饱和部分取代的甲基的5-氯尿嘧啶/胸腺嘧啶的合成和人胸苷磷酸化酶的抑制活性

  摘要：

  Abstractmagnified imageBy attaching (methyl)‐ or (difluoromethyl)‐phosphonate groups to the 1‐positions of ethene, cyclopentene or benzene, and attaching 1‐(methyl)‐5‐chlorouracil or 1‐(methyl)thymine groups to the corresponding 2‐positions, compounds 1–5 were prepared as potential inhibitors of recombinant human thymidine phosphorylase (TP). The products were designed to mimic the interatomic distance (ca. 3.41 Å) between the incoming phosphate and leaving pyrimidine groups at the transition state for the putative SN2 mechanism of TP. Free rotation around the (unsaturated‐CH2)–pyrimidine bonds in 1–5 enabled a span of ca. 2.40–4.40 Å between the CH2 or CF2 C‐atoms in the phosphonates and N(1) of the pyrimidines to be covered. The products were found to be ineffective inhibitors, and some reasons for this are given.

  DOI：

  10.1002/hlca.200900003
• 作为产物：
  描述：

  diethyl {difluoro[2-(hydroxymethyl)cyclopent-1-en-1-yl]methyl}phosphonate 、 N-3-benzoylthymine 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 diethyl ({2-[(3-benzoyl-3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl}(difluoro)methyl)phosphonate
  参考文献：
  名称：

  在N（1）上具有1- [膦基（甲基/二氟甲基）]-1,2-不饱和部分取代的甲基的5-氯尿嘧啶/胸腺嘧啶的合成和人胸苷磷酸化酶的抑制活性

  摘要：

  Abstractmagnified imageBy attaching (methyl)‐ or (difluoromethyl)‐phosphonate groups to the 1‐positions of ethene, cyclopentene or benzene, and attaching 1‐(methyl)‐5‐chlorouracil or 1‐(methyl)thymine groups to the corresponding 2‐positions, compounds 1–5 were prepared as potential inhibitors of recombinant human thymidine phosphorylase (TP). The products were designed to mimic the interatomic distance (ca. 3.41 Å) between the incoming phosphate and leaving pyrimidine groups at the transition state for the putative SN2 mechanism of TP. Free rotation around the (unsaturated‐CH2)–pyrimidine bonds in 1–5 enabled a span of ca. 2.40–4.40 Å between the CH2 or CF2 C‐atoms in the phosphonates and N(1) of the pyrimidines to be covered. The products were found to be ineffective inhibitors, and some reasons for this are given.

  DOI：

  10.1002/hlca.200900003