4-fluoro-3-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-fluoro-3-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentanoic acid
• 英文别名: (Z)-4-fluoro-3-[2-[[(4-methoxyphenyl)-diphenylmethyl]amino]ethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)pent-3-enoic acid
• 化学式: C₃₂H₃₂FN₃O₅
• 分子量: 557.622
• InChiKey: RBQWBHGBOVXCFS-NFFVHWSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-羟基戊二酸二乙酯 在 Lindlar's catalyst 吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 正丁基锂 、 2-甲基-2-丁烯 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氢气 、 戴斯-马丁氧化剂 、 三苯基膦 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 22.5h， 生成 4-fluoro-3-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pentanoic acid
  参考文献：
  名称：

  Fluorinated Peptide Nucleic Acid

  摘要：

  The fluorinated olefinic peptide nucleic acid analogue (F-OPA) monomer containing the base thymine was synthesised in 13 steps. PNAs containing this unit were prepared and their pairing properties assessed by means of UV-melting experiments.

  DOI：

  10.1081/ncn-120022833

文献信息

• Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers
  作者：Marcel Hollenstein、Christian J. Leumann

  DOI：10.1021/ol034579s

  日期：2003.5.1

  [GRAPHIC]A fluorinated OPA monomer containing the base thymine ((Z)-t-F-OPA) was synthesized in 12 steps, featuring a highly selective allylic over homoallylic Mitsunobu substitution for the introduction of the nucleobase. F-OPA modified PNA decamers were prepared by the MMTr/acyl protection strategy. The thermal stability of duplexes of PNA decamers containing (2)-t-F-OPA units with antiparallel complementary DNA was measured. We found a strong dependence of stability from the sequential position of the (2)-t-F-OPA units, ranging from DeltaT(m) of +2.4 to -8.1 degreesC/modification relative to unmodified PNA.
• Fluorinated Peptide Nucleic Acid
  作者：Marcel Hollenstein、Daniel Gautschi、Christian J. Leumann

  DOI：10.1081/ncn-120022833

  日期：2003.10

  The fluorinated olefinic peptide nucleic acid analogue (F-OPA) monomer containing the base thymine was synthesised in 13 steps. PNAs containing this unit were prepared and their pairing properties assessed by means of UV-melting experiments.