tert-butyl [5-(trifluoromethyl)uracil-N¹-yl]acetate | 1434143-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl [5-(trifluoromethyl)uracil-N¹-yl]acetate
• 英文别名: Tert-butyl 2-[2,4-dioxo-5-(trifluoromethyl)pyrimidin-1-yl]acetate；tert-butyl 2-[2,4-dioxo-5-(trifluoromethyl)pyrimidin-1-yl]acetate
• CAS: 1434143-39-1
• 化学式: C₁₁H₁₃F₃N₂O₄
• 分子量: 294.23
• InChiKey: WOJYLANAYLPMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl [5-(trifluoromethyl)uracil-N¹-yl]acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(2,4-Dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)acetic acid
  参考文献：
  名称：

  Synthesis of Fluorine-Labeled Peptide Nucleic Acid Building Blocks as Sensors for the ¹⁹F NMR Spectroscopic Detection of Different Hybridization Modes

  摘要：

  Peptide nucleic acid (PNA) building blocks, bearing a fluorine sensor at C-5 of the uracil base [viz. trifluoromethyl and 3,3-bis(trifluoromethyl)-4,4,4-trifluorobut-1-ynyl], were synthesized and incorporated to a PNA strand, and their applicability for the monitoring of different hybridization modes by F-19 NMR spectroscopy was studied. Both sensors gave unique F-19 resonance shifts in NMR when the PNA was targeted to a complementary antiparallel DNA, antiparallel RNA, parallel DNA, and parallel RNA. The 5-trifluoromethyl-derived sensor was additionally applied for the monitoring of interconversions from a parallel DNA/PNA complex to an antiparallel RNA/PNA complex and from a PNA/PNA complex to two DNA/PNA complexes (i.e., double-duplex invasion).

  DOI：

  10.1021/jo400014y
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 5-三氟甲基尿嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到tert-butyl [5-(trifluoromethyl)uracil-N¹-yl]acetate
  参考文献：
  名称：

  Synthesis of Fluorine-Labeled Peptide Nucleic Acid Building Blocks as Sensors for the ¹⁹F NMR Spectroscopic Detection of Different Hybridization Modes

  摘要：

  Peptide nucleic acid (PNA) building blocks, bearing a fluorine sensor at C-5 of the uracil base [viz. trifluoromethyl and 3,3-bis(trifluoromethyl)-4,4,4-trifluorobut-1-ynyl], were synthesized and incorporated to a PNA strand, and their applicability for the monitoring of different hybridization modes by F-19 NMR spectroscopy was studied. Both sensors gave unique F-19 resonance shifts in NMR when the PNA was targeted to a complementary antiparallel DNA, antiparallel RNA, parallel DNA, and parallel RNA. The 5-trifluoromethyl-derived sensor was additionally applied for the monitoring of interconversions from a parallel DNA/PNA complex to an antiparallel RNA/PNA complex and from a PNA/PNA complex to two DNA/PNA complexes (i.e., double-duplex invasion).

  DOI：

  10.1021/jo400014y