N⁶-(1-adamantyl)adenine | 19143-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N⁶-(1-adamantyl)adenine
• 英文别名: 6-Adamantylamino-purin；adamantan-1-yl-(7(9)H-purin-6-yl)-amine；n6-Adamantyladenine；N-(1-adamantyl)-7H-purin-6-amine
• CAS: 19143-77-2
• 化学式: C₁₅H₁₉N₅
• 分子量: 269.349
• InChiKey: BQNQPHYLGUPBGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-金刚烷醇 、 腺嘌呤 在 三氟乙酸 作用下， 反应 8.0h， 以73%的产率得到N⁶-(1-adamantyl)adenine
  参考文献：
  名称：

  Studies on the Adamantylation ofN-Heterocycles and Nucleosides

  摘要：

  Adamantylation of several N-heterocycles and of two ribonucleosides (uridine and toyocamycin) was studied. The exact substitution position by the adamantyl carbocation generated tram adamantan-1-ol in CF3COOH depends on the nature of the heterocyclic substrate. Thus, adamantylation of an additional exocyclic amino group (see Scheme 1), N-adamantylation of the heterocycle (Scheme 2), C-adamantylation of the heterocycle (Scheme 3), as well as the formation of heterocyclic N-adamantylcarboxamides via the Ritter reaction (Scheme 4) are possible. The structures of the reaction products were determined by means of elemental analysis and NMR, UV,and IR spectroscopy.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2020::aid-hlca2020>3.0.co;2-p