5-(perfluorobutyl)pyrimidine-2,4(1H,3H)-dione | 58671-28-6

• 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-(perfluorobutyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-Perfluorobutyl uracil；5-nonafluorobutyl-1H-pyrimidine-2,4-dione；5-nonafluorobutyldihydrouracil；5-Nonafluorbutyl-pyrimidin-2,4-dion；5-n-Perfluorbutyl-uracil；5-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1H-pyrimidine-2,4-dione
• CAS: 58671-28-6
• 化学式: C₈H₃F₉N₂O₂
• 分子量: 330.11
• InChiKey: RXUXOXUTRBXSOE-UHFFFAOYSA-N

物化性质

• 密度：
  1.665±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  全氟碘代丁烷 、 尿嘧啶 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以90%的产率得到5-(perfluorobutyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  不含催化剂的可见光可促进尿嘧啶和胞嘧啶的三氟甲基化和全氟烷基化†

  摘要：

  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。

  DOI：

  10.1039/c8cc07759b

文献信息

• A general and green fluoroalkylation reaction promoted <i>via</i> noncovalent interactions between acetone and fluoroalkyl iodides
  作者：Ting Mao、Ming-Jian Ma、Liang Zhao、De-Pu Xue、Yanbo Yu、Jiwei Gu、Chun-Yang He

  DOI：10.1039/c9cc09517a

  日期：——

  The first example of visible light promoted fluoroalkylation reactions initiated via noncovalent interactions between acetone and fluoroalkyl iodides is presented. The reaction system features synthetic simplicity, mild reaction conditions without any photoredox catalyst, and high functional group tolerance. A wide range of substrate scopes such as alkenes, alkynes and (hetero)arenes were all compatible

  提出了通过丙酮和氟代烷基碘之间的非共价相互作用引发的可见光促进的氟代烷基化反应的第一个例子。该反应系统具有合成简单，反应条件温和，无任何光氧化还原催化剂和高官能团耐受性的特点。各种各样的底物范围，如烯烃，炔烃和（杂）芳烃都与反应体系兼容。
• Perfluoroalkylation of purine and pyrimidine bases by electrochemically induced SRN1 substitution.
  作者：Maurice Médebielle、Jean Pinson、Jean-Michel Savéant

  DOI：10.1016/s0040-4039(00)60185-5

  日期：1992.11

  Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl iodides in the presence of purine and pyrimidine anions yields the correspon C-perfluoroalkylated purines and pyrimidines by an SRN1 mechanism.

  在嘌呤和嘧啶阴离子存在下，通过芳香族阴离子介体间接电化学还原全氟烷基碘，通过S RN 1机理产生相应的C-全氟烷基化嘌呤和嘧啶。
• 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。
• 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
• A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced S_RN1 Substitution
  作者：Maurice Médebielle、Mehmet Ali Oturan、Jean Pinson、Jean-Michel Savéant

  DOI：10.1021/jo9515541

  日期：1996.1.1

  Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl halides (CF3Br, n-C4F9I, n-C6F13I, I(CF2)(4)I) in the presence of imidazole, 4(5)-nitroimidazole, 2-methyl-5-nitroimidazole, 2-(4'-methoxyphenyl)imidazole, imidazole-2-carboxaldehyde, 4(5)-nitroimidazole-2-carboxaldehyde, 5(6)-nitrobenzimidazole, purines (adenine, hypoxanthine, xanthine, theophylline, lumazine) and pyrimidine anions (uracil, cytosine, barbituric acid) yields the corresponding C-perfluoroalkylated nitrogen bases by an S(RN)1 mechanism. Aromatic nucleophilic substitution of some fluorinated aryl halides 1-iodo-2-(trifluoromethyl)benzene and 1-(4'-iodo-tetrafluorophenyl)-imidazole was also investigated and it was found that 1-iodo-2-(trifluoromethyl)benzene could react successfully under redox-catalyzed conditions with imidazole, 2-(4'-methoxyphenyl)imidazole anion, and uracil anion to give the corresponding 5-(fluorinated-aryl) nitrogen bases. In the case of 1-(4'iodo-tetrafluorophenyl)imidazole, direct electrochemical radical nucleophilic substitution with 2-methyl-5-nitroimidazole and uracil was possible in DMSO. In this way new, 4-[2',3',5',6'-tetrafluoro-4'-(imidazol-1 ''-yl)phenyl] nitrogen bases were obtained in good yields.