5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate | 65499-42-5

• 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-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate
• 英文别名: 3',5'-di-O-acetyl-5-trifluoromethyl-2'-deoxyuridine；5-trifluoromethyl-3',5'-di-O-acetyl-2'-deoxyuridine；Thymidine, alpha,alpha,alpha-trifluoro-, 3',5'-diacetate；[(2R,3S,5R)-3-acetyloxy-5-[2,4-dioxo-5-(trifluoromethyl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 65499-42-5
• 化学式: C₁₄H₁₅F₃N₂O₇
• 分子量: 380.278
• InChiKey: UNTYIYCXVYMWKI-HBNTYKKESA-N

物化性质

• 熔点：
  50-54 °C
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以84%的产率得到三氟胸苷
  参考文献：
  名称：

  Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated ¹⁸F-trifluoromethylation procedure

  摘要：

  自动化的¹⁸F-三氟甲基化提供了首个[¹⁸F]三氟胸苷的放射合成，该化合物显示出作用机制的PET探针潜力。

  DOI：

  10.1039/c8ob00432c
• 作为产物：
  描述：

  碘苷 在 吡啶 、 potassium fluoride 、 copper(l) iodide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.5h， 生成 5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate
  参考文献：
  名称：

  Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated ¹⁸F-trifluoromethylation procedure

  摘要：

  自动化的¹⁸F-三氟甲基化提供了首个[¹⁸F]三氟胸苷的放射合成，该化合物显示出作用机制的PET探针潜力。

  DOI：

  10.1039/c8ob00432c

文献信息

• Enzymatic synthesis of perfluoroalkylated DNA
  作者：Bastian Holzberger、Andreas Marx

  DOI：10.1016/j.bmc.2009.03.063

  日期：2009.5

  Thymidine analogues 5-trifluoromethyl-, 5-pentafluoroethyl- and 5-(heptafluoro-n-propyl)-2′-deoxyuridines were synthesised and converted into the corresponding 5′-triphosphates 1a–c. Performing DNA polymerase-catalyzed primer extension reactions these modified nucleotides were incorporated into DNA to create perfluoroalkylated nucleic acids. Although single modified nucleotides were enzymatically incorporated

  合成了胸苷类似物5-三氟甲基-，5-五氟乙基-和5-（七氟-正丙基）-2'-脱氧尿苷，并将其转化为相应的5'-三磷酸酯1a – c。进行DNA聚合酶催化的引物延伸反应，将这些修饰的核苷酸掺入DNA以产生全氟烷基化的核酸。尽管单个修饰的核苷酸被酶促地掺入并进一步延伸，与天然TTP十分相似，但是多重修饰的核酸的酶促合成仅在每四个碱基进行修饰的情况下才是最初可行的。但是，由于修饰的dUTP对DNA聚合酶的影响随所用酶的不同而有很大差异，Therminator DNA聚合酶擅长掺入11个相邻的5-trifluoromethyl-2'-deoxyuridine部分。
• 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。
• Nucleobase having perfluoroalkyl group and process for producing the same
  申请人：Tosoh Corporation

  公开号：US07884202B2

  公开（公告）日：2011-02-08

  Nucleobases are perfluoroalkylated in a one step process with a perfluoroalkyl halide in the presence of a sulfoxide, a peroxide and an iron compound. Compounds so produced are useful as medicinal drugs, intermediates for medicinal drugs and agricultural chemicals.

  核碱基可以在有亚砜、过氧化物和铁化合物的存在下，通过一步法与全氟烷基卤化物进行全氟烷基化。这样产生的化合物可用作药物、药物中间体和农药。
• 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。
• Synthesis of nucleoside-based antiviral drugs in ionic liquids
  作者：Vineet Kumar、Sanjay V. Malhotra

  DOI：10.1016/j.bmcl.2008.08.090

  日期：2008.10

  Nucleoside-based antiviral drugs have been synthesized using imidazolium-based ionic liquids as reaction medium. The ionic liquids were proved to be better solvents for all the nucleoside in terms of solubility and reaction medium as compared to conventional molecular solvents. (C) 2008 Elsevier Ltd. All rights reserved.