3-(2-azidoethyl)-4-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pent-3-enoic acid | 552308-09-5

• 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: 3-(2-azidoethyl)-4-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pent-3-enoic acid
• 英文别名: (Z)-3-(2-azidoethyl)-4-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)pent-3-enoic acid
• CAS: 552308-09-5
• 化学式: C₁₂H₁₄FN₅O₄
• 分子量: 311.273
• InChiKey: XLOQJAVPKZMTHS-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(2-azidoethyl)-4-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pent-3-enoic acid 在 吡啶 、 三苯基膦 、 氨 作用下， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers

  摘要：

  [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.

  DOI：

  10.1021/ol034579s
• 作为产物：
  描述：

  2-fluoro-5-[(4-methoxyphenyl)diphenylmethoxy]-3-{2-[(4-methoxyphenyl)diphenyl-methoxy]ethyl}-pent-2-enoic acid ethyl ester 在 咪唑 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 cerium(III) chloride 、 叠氮化锂 、 2-甲基-2-丁烯 、 四溴化碳 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三氯化硼 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 65.5h， 生成 3-(2-azidoethyl)-4-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pent-3-enoic acid
  参考文献：
  名称：

  Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers

  摘要：

  [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.

  DOI：

  10.1021/ol034579s

文献信息

• 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.