5-(tridecafluorohexyl)uridine | 58671-32-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(tridecafluorohexyl)uridine
• 英文别名: uridine, 5-tridecafluorohexyl-；1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(perfluorohexyl)pyrimidine-2,4(1H,3H)-dione；5-Perfluorhexyl-uracil；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)pyrimidine-2,4-dione
• CAS: 58671-32-2
• 化学式: C₁₅H₁₁F₁₃N₂O₆
• 分子量: 562.241
• InChiKey: KUGJPYIIQHQEJQ-UAKXSSHOSA-N

物化性质

• 密度：
  1.789±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  4,2',3',5'-Tetrakis-(O-trimethylsilyl)-uracil 在 水 作用下， 以 1,1,2-三氯三氟乙烷（CFC-113） 、 乙酸乙酯 为溶剂， 反应 23.5h， 生成 5-(tridecafluorohexyl)uridine
  参考文献：
  名称：

  Facile perfluoroalkylation of uracils and uridines at the C-5 position

  摘要：

  Perfluoroalkylation at the C-5 position of uracil has been achieved in yields of 38-56% by the reaction of its bis(trimethylsilyl) derivative with bis(perfluoroalkanoyl) peroxides and the hydrolytic deprotection of the silylated products. A substituent or nitrogen replacement at C-6 does not interfere with perfluoroalkylation at C-5, but no significant reaction occurs at C-6 when C-5 is blocked.

  DOI：

  10.1016/s0022-1139(00)80396-6

文献信息

• Benign perfluoroalkylation of uracils and uracil nucleosides via visible light-induced photoredox catalysis
  作者：Ben-Hou Zhang、Jing-Jing Kong、Yang Huang、Yue-Guang Lou、Xiao-Fei Li、Chun-Yang He

  DOI：10.1016/j.cclet.2017.03.039

  日期：2017.8

  Abstract In this work, an efficient and facile method for the preparation of 5-perfluoroalkylation uracils and uracil nucleosides through visible-light-mediated reaction has been developed. The reaction processes in high efficiency under mild reaction conditions and show broad substrate scope by employing commercial available perfluoroalkyl sources, thus demonstrates high potent application in life

  摘要在这项工作中，开发了一种通过可见光介导的反应制备5-全氟烷基化尿嘧啶和尿嘧啶核苷的简便快捷方法。该反应过程在温和的反应条件下高效进行，并且通过使用可商购的全氟烷基源显示了广阔的底物范围，因此证明了在生命和医学领域的高效应用。
• Facile perfluoroalkylation of uracils and uridines at the C-5 position
  作者：Masakazu Nishida、Shozo Fujii、Hiroshi Kimoto、Yoshio Hayakawa、Hideo Sawada、Louis A. Cohen

  DOI：10.1016/s0022-1139(00)80396-6

  日期：1993.7

  Perfluoroalkylation at the C-5 position of uracil has been achieved in yields of 38-56% by the reaction of its bis(trimethylsilyl) derivative with bis(perfluoroalkanoyl) peroxides and the hydrolytic deprotection of the silylated products. A substituent or nitrogen replacement at C-6 does not interfere with perfluoroalkylation at C-5, but no significant reaction occurs at C-6 when C-5 is blocked.