4-Amino-5-furan-3-yl-pyrimidin-2-ol | 137937-85-0

• 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: 4-Amino-5-furan-3-yl-pyrimidin-2-ol
• 英文别名: 6-amino-5-(furan-3-yl)-1H-pyrimidin-2-one
• CAS: 137937-85-0
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: SIJJADISVNSMLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5-Furan-3-yl-2-trimethylsilanyloxy-pyrimidin-4-yl)-trimethylsilanyl-amine 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-Amino-5-furan-3-yl-pyrimidin-2-ol
  参考文献：
  名称：

  各种5-芳基取代的胞嘧啶的合成

  摘要：

  已评估了某些Pd催化的偶联反应可合成5取代的胞嘧啶。通过将2，4 - O，N-双-三甲基甲硅烷基-5-碘胞嘧啶与各种芳基锡化合物一起使用，以高收率制备了大量5-芳基胞嘧啶。已证明使用三甲基甲硅烷基对于该反应是必不可少的，尝试将5-碘胞嘧啶和2-三甲基苯乙烯基噻唑偶联是不成功的。不幸的是未成功的一种方便的替代方案是将偶联官能团反转并使商用的芳基卤化物与5-三甲基锡烷基-或5-三丁基锡烷基衍生物或相应的2,4 - O，N-双-三烷基甲硅烷基胞嘧啶偶联。

  DOI：

  10.1002/jhet.5570280626

文献信息

• Fluorescent Nucleoside Analogs That Mimic Naturally Occurring Nucleosides
  申请人：Tor Yitzhak

  公开号：US20080261823A1

  公开（公告）日：2008-10-23

  The present invention provides fluorescent nucleoside analogs with conjugated membered heterocycles, including furan and thiophene. The fluorescent nucleoside analogs maintain structural similarity to naturally occurring nucleoside bases, mimicking shape, size, hybridization, and recognition properties. Incorporation of the fluorescent cyclic compounds confers specific photophysical characteristics including a bathochromic (red) shift of the absorption spectrum to minimize absorption overlap with naturally occurring nucleoside bases, and a shift to the long emission wavelength in the visible range. The invention also provides for various methods of synthesizing the fluorescent nucleoside analogs and incorporating the fluorescent analogs in DNA, RNA, or oligomer synthesis. Further, methods of detecting the fluorescent nucleoside analogs in an oligonucleotide or oligomer are provided. The subject compounds are useful as probes in the study of the structure and dynamics of nucleic acids and their complexes with proteins.
• [EN] FLUORESCENT NUCLEOSIDE ANALOGS THAT MIMIC NATURALLY OCCURRING NUCLEOSIDES<br/>[FR] ANALOGUES NUCLEOSIDIQUES FLUORESCENTS IMITANT DES NUCLEOSIDES NATURELS
  申请人：UNIV CALIFORNIA

  公开号：WO2006076102A2

  公开（公告）日：2006-07-20

  [EN] The present invention provides fluorescent nucleoside analogs with conjugated membered heterocycles, including furan and thiophene. The fluorescent nucleoside analogs maintain structural similarity to naturally occurring nucleoside bases, mimicking shape, size, hybridization, and recognition properties. Incorporation of the fluorescent cyclic compounds confers specific photophysical characteristics including a bathochromic (red) shift of the absorption spectrum to minimize absorption overlap with naturally occurring nucleoside bases, and a shift to the long emission wavelength in the visible range. The invention also provides for various methods of synthesizing the fluorescent nucleoside analogs and incorporating the fluorescent analogs in DNA, RNA, or oligomer synthesis. Further, methods of detecting the fluorescent nucleoside analogs in an oligonucleotide or oligomer are provided. The subject compounds are useful as probes in the study of the structure and dynamics of nucleic acids and their complexes with proteins.
  [FR] La présente invention concerne ces analogues nucléosidiques fluorescents avec hétérocycles à 5 éléments conjugués, comprenant le furane et le thiophène. Lesdits analogues présentent une similitude avec des bases nucléosidiques naturelles, dont ils imitent la forme, la taille ainsi que les propriétés d'hybridation et de reconnaissance. L'incorporation des composés cycliques fluorescents confèrent des caractéristiques photophysiques spécifiques, dont un décalage bathochrome (vers le rouge) du spectre d'absorption qui réduit le chevauchement d'absorption avec les bases nucléosidiques naturelles, et un décalage de la longueur d'onde à émission longue dans la plage visible. L'invention concerne également diverses méthodes de synthèse des analogues nucléosidiques fluorescents et d'incorporation desdits analogues dans l'ADN, l'ARN ou la synthèse d'oligomères. Sont également décrites des méthodes de détection d'analogues nucléosidiques fluorescents dans un oligonucléotide ou un oligomère. Les composés de l'invention conviennent en tant que sondes dans l'étude de la structure et de la dynamique des acides nucléiques et des complexes qu'ils forment avec des protéines.
• Synthesis of various 5-arylsubstituted cytosines
  作者：Dan Peters、Anna-Britta Hörnfeldt、Salo Gronowitz

  DOI：10.1002/jhet.5570280626

  日期：1991.10

  Some Pd-catalyzed coupling reactions have been evaluated for the synthesis of 5-substituted cytosines. A large number of 5-arylcytosines were prepared in good yields by using 2,4-O,N-bis-trimethylsilyl-5-iodocytosine with various aryl tin compounds. The use of trimethylsilyl groups proved to be essential for the reaction, attempted coupling of 5-iodocytosine and 2-trimethylstannylthiazole was not successful

  已评估了某些Pd催化的偶联反应可合成5取代的胞嘧啶。通过将2，4 - O，N-双-三甲基甲硅烷基-5-碘胞嘧啶与各种芳基锡化合物一起使用，以高收率制备了大量5-芳基胞嘧啶。已证明使用三甲基甲硅烷基对于该反应是必不可少的，尝试将5-碘胞嘧啶和2-三甲基苯乙烯基噻唑偶联是不成功的。不幸的是未成功的一种方便的替代方案是将偶联官能团反转并使商用的芳基卤化物与5-三甲基锡烷基-或5-三丁基锡烷基衍生物或相应的2,4 - O，N-双-三烷基甲硅烷基胞嘧啶偶联。