8-hydroxy-9-phenyladenine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-hydroxy-9-phenyladenine
• 英文别名: 6-amino-9-phenyl-7H-purin-8-one
• 化学式: C₁₁H₉N₅O
• 分子量: 227.225
• InChiKey: NGUOEGOTXKJOGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-氯-9-苯基嘌呤 在 ammonium hydroxide 、 甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 37.0h， 生成 8-hydroxy-9-phenyladenine
  参考文献：
  名称：

  Synthetic Strategies to 9-Substituted 8-Oxoadenines

  摘要：

  Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.642051

文献信息

• Efficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives
  作者：Kosaku Hirota、Kazunori Kazaoka、Itaru Niimoto、Hironao Sajiki

  DOI：10.1039/b300557g

  日期：2003.4.14

  An efficient and general method for the synthesis of 2,9-disubstituted 8-hydroxyadenines, which are expected to have various biological activities, was realized. 5-Amino-4-cyano-2-hydroxyimidazoles (1) were prepared from aminomalononitrile and isocyanates as key intermediates. The condensation of 1a with amidines, imidates, guanidine, urea and thioureas afforded 8-hydroxyadenines (2–6) possessing various substituents at the 2-position. Furthermore, selective alkylation of 2-amino- and 2-hydroxyadenines (4 and 6) successively proceeded to give the corresponding 2-alkylamino- and 2-alkoxyadenines (5 and 7), respectively. 2-Alkylthioadenines (15) were prepared by an analogous reaction of 1a with benzoyl isothiocyanate and subsequent S-alkylation. The imidazoles 1 are most useful intermediates for the synthesis of 8-hydroxyadenine derivatives.

  一种高效且通用的方法被实现，用于合成预期具有多种生物活性的2,9-二取代的8-羟基腺苷。5-氨基-4-氰基-2-羟基咪唑（1）是从氨基丙腈和异氰酸酯作为关键中间体制备的。将1a与氨基脲、咪唑、胍、尿素和硫脲缩合，得到在2位具有各种取代基的8-羟基腺苷（2–6）。此外，对2-氨基和2-羟基腺苷（4和6）进行选择性烷基化，顺利实现，分别得到相应的2-烷基氨基和2-烷氧腺苷（5和7）。2-烷基硫腺苷（15）是通过1a与苯甲酰异硫氰酸酯的类似反应以及随后S-烷基化制备的。咪唑类化合物1是合成8-羟基腺苷衍生物最有用的中间体。
• Novel and Efficient Synthesis of 8-Oxoadenine Derivatives
  作者：Kosaku Hirota、Kazunori Kazaoka、Itaru Niimoto、Hironao Sajiki

  DOI：10.3987/com-01-9356

  日期：——

  A novel synthetic method of 8-oxoadenine derivatives (3 and 4) is reported. This widely applicable synthetic method was realized through the use of 5-aminlo-4-cyano-2-oxoimidazole derivatives (2) as the key intermediates. A variety of substituents were successfully introduced to the 2- and 9-position of the 8-oxoadenine nucleus.