tert-butyl [N³-(4-methoxybenzyl)-5-(3,3-bis(trifluoromethyl)-4,4,4-trifluoro-1-butynyl)uracil-N1-yl]acetate | 1434143-42-6

• 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 [N³-(4-methoxybenzyl)-5-(3,3-bis(trifluoromethyl)-4,4,4-trifluoro-1-butynyl)uracil-N1-yl]acetate
• 英文别名: Tert-butyl 2-[3-[(4-methoxyphenyl)methyl]-2,4-dioxo-5-[4,4,4-trifluoro-3,3-bis(trifluoromethyl)but-1-ynyl]pyrimidin-1-yl]acetate；tert-butyl 2-[3-[(4-methoxyphenyl)methyl]-2,4-dioxo-5-[4,4,4-trifluoro-3,3-bis(trifluoromethyl)but-1-ynyl]pyrimidin-1-yl]acetate
• CAS: 1434143-42-6
• 化学式: C₂₄H₂₁F₉N₂O₅
• 分子量: 588.427
• InChiKey: JQXMYJLPWCKHTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl [N³-(4-methoxybenzyl)-5-(3,3-bis(trifluoromethyl)-4,4,4-trifluoro-1-butynyl)uracil-N1-yl]acetate 在 ammonium cerium (IV) nitrate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 tert-butyl N-[N-(9-fluorenylmethoxycarbonyl)-2-aminoethyl]-N-[5-[3,3-bis(trifluoromethyl)-4,4,4-trifluorobut-1-ynyl]uracil-N¹-yl]-acetylglycinate
  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：

  tert-butyl (5-iodouracil-1-yl)acetate 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 tert-butyl [N³-(4-methoxybenzyl)-5-(3,3-bis(trifluoromethyl)-4,4,4-trifluoro-1-butynyl)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

文献信息

• Synthesis of Fluorine-Labeled Peptide Nucleic Acid Building Blocks as Sensors for the ¹⁹F NMR Spectroscopic Detection of Different Hybridization Modes
  作者：Anu Kiviniemi、Merita Murtola、Petri Ingman、Pasi Virta

  DOI：10.1021/jo400014y

  日期：2013.6.7

  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).