N-(7(9)H-purin-6-yl)-phthalimide | 54707-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(7(9)H-purin-6-yl)-phthalimide
• 英文别名: n6-Phthaloyladenin；2-(7H-purin-6-yl)isoindole-1,3-dione
• CAS: 54707-67-4
• 化学式: C₁₃H₇N₅O₂
• 分子量: 265.231
• InChiKey: JNDFOPDDJGCCBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(7(9)H-purin-6-yl)-phthalimide 、 1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 sodium hydride 作用下， 以 乙腈 、 mineral oil 为溶剂， 反应 1.0h， 以36%的产率得到
  参考文献：
  名称：

  Tetramethylsuccinimide as a Directing/Protecting Group in Purine Glycosylations

  摘要：

  Tetra methylsuccinic anhydride can be used to protect the exocyclic amine of 6-aminopurine derivatives by forming the corresponding tetramethysuccinimide. X-ray crystallography confirms that the imide carbonyl and the methyl groups are positioned to sterically block the N7 nitrogen so that glycosylations occur with very high regiochemical control at N9. This approach Is particularly effective for 3-substituted purines where the substituent tends to block access to N9 and inhibit glycosylation at that site.

  DOI：

  10.1021/ol9025028

文献信息

• Phosphonomethylthio-alkoseypureine derivatives, intermediate products for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0399743A1

  公开（公告）日：1990-11-28

  Compounds of formula (I), and pharmaceutically acceptable salts thereof: wherein R₁ is hydroxy or amino; R₂ is hydrogen or amino; R₃ is hydrogen, hydroxymethyl or acyloxymethyl; R₄ is a group of formula: wherein R₅ and R₆ are independently selected from hydrogen, C₁₋₆ alkyl and optionally substituted phenyl; or R₃ and R₄ together are: wherein R₆ is as defined above; having antiviral activity, processes for their preparation and their pharmaceutical use.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 R₁ 是羟基或氨基； R₂ 是氢或氨基 R₃ 是氢、羟甲基或酰氧基甲基； R₄ 是式中的基团： 其中 R₅ 和 R₆ 独立选自氢、C₁₋₆ 烷基和任选取代的苯基；或 R₃ 和 R₄ 合在一起为 其中 R₆ 如上文所定义； 具有抗病毒活性，其制备工艺和药物用途。
• Tetramethylsuccinimide as a Directing/Protecting Group in Purine Glycosylations
  作者：Joseph W. Arico、Amy K. Calhoun、Kerry J. Salandria、Larry W. McLaughlin

  DOI：10.1021/ol9025028

  日期：2010.1.1

  Tetra methylsuccinic anhydride can be used to protect the exocyclic amine of 6-aminopurine derivatives by forming the corresponding tetramethysuccinimide. X-ray crystallography confirms that the imide carbonyl and the methyl groups are positioned to sterically block the N7 nitrogen so that glycosylations occur with very high regiochemical control at N9. This approach Is particularly effective for 3-substituted purines where the substituent tends to block access to N9 and inhibit glycosylation at that site.