5-(perfluorohexyl)pyrimidine-2,4(1H,3H)-dione | 58671-29-7

• 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: 5-(perfluorohexyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-(tridecafluorohexyl)uracil；5-tridecafluorohexyl-1H-pyrimidine-2,4-dione；5-perfluorohexyluracil；5-Perfluorhexyl-pyrimidin-2,4-dion；Uracil, 5-tridecafluorohexyl-；5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-1H-pyrimidine-2,4-dione
• CAS: 58671-29-7
• 化学式: C₁₀H₃F₁₃N₂O₂
• 分子量: 430.125
• InChiKey: PLCJTKJJJMWPBA-UHFFFAOYSA-N

物化性质

• 密度：
  1.699±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  在 水 作用下， 以 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 反应 2.0h， 生成 5-(perfluorohexyl)pyrimidine-2,4(1H,3H)-dione
  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。
• Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines
  作者：Yang Huang、Yun-Yun Lei、Liang Zhao、Jiwei Gu、Qiuli Yao、Ze Wang、Xiao-Fei Li、Xingang Zhang、Chun-Yang He

  DOI：10.1039/c8cc07759b

  日期：——

  perfluoroalkyl motifs in the core structure, access to such analogues typically requires multi-step synthesis. Here, we report a mild, metal-free and operationally simple strategy for the direct perfluoroalkylation of uracils, cytosines and pyridinones through a visible-light induced pathway from perfluoroalkyl iodides. This photochemical transformation features synthetic simplicity, mild reaction

  氟烷基化的烯胺酮，例如三氟吡啶和5-三氟甲基尿嘧啶，在药物和农用化学品中具有广泛的应用。尽管这类药物通常在核心结构中带有CF 3和全氟烷基基序，但要获得此类类似物通常需要多步合成。在这里，我们报告了一种温和，无金属且操作简单的策略，可通过可见光诱导的全氟烷基碘化物途径，直接对尿嘧啶，胞嘧啶和吡啶酮进行全氟烷基化。这种光化学转化具有合成简单，反应条件温和，无任何光氧化还原催化剂以及高官能团耐受性的特点，为在药物化学中的应用提供了便捷的途径。
• Nucleobase Having Perfluoroalkyl Group and Process for Producing the Same
  申请人：Yamakawa Tetsu

  公开号：US20090124796A1

  公开（公告）日：2009-05-14

  Provided is a simple and efficient production process of a nucleobase having a perfluoroalkyl group. A nucleobase (for example, uracils, cytosines, adenines, guanines, hypoxanthines, xanthines, or the like) is reacted with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound to produce a perfluoroalkyl-substituted nucleobase, which is useful as an intermediate for medical drugs, economically.

  提供一种具有全氟烷基的核碱的简单高效的生产工艺。将核碱（例如尿嘧啶、胞嘧啶、腺嘌呤、鸟嘌呤、次黄嘌呤、黄嘌呤等）与全氟烷基卤化物在亚砜、过氧化物和铁化合物的存在下反应，制得全氟烷基取代的核碱，该中间体在医药制剂中具有经济价值。
• NUCLEIC ACID BASE HAVING PERFLUOROALKYL GROUP AND METHOD FOR PRODUCING THE SAME
  申请人：Tosoh Corporation

  公开号：EP1947092A1

  公开（公告）日：2008-07-23

  Provided is a simple and efficient production process of a nucleobase having a perfluoroalkyl group. A nucleobase (for example, uracils, cytosines, adenines, guanines, hypoxanthines, xanthines, or the like) is reacted with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound to produce a perfluoroalkyl-substituted nucleobase, which is useful as an intermediate for medical drugs, economically.

  本发明提供了一种具有全氟烷基的核碱基的简单而高效的生产工艺。 核碱基（例如尿嘧啶、胞嘧啶、腺嘌呤、鸟嘌呤、次黄嘌呤、黄嘌呤或类似物）在亚砜、过氧化物和铁化合物的存在下与全氟烷基卤化物反应，生成全氟烷基取代的核碱基，该核碱基可经济地用作医疗药物的中间体。
• Method for producing nucleic acid base having perfluoroalkyl group
  申请人：Tosoh Corporation

  公开号：EP1947092B1

  公开（公告）日：2015-04-15