8-bromo-2,6-dichloro-9-[(4-methylphenyl)methyl]-9H-purine | 1246307-22-1

• 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: 8-bromo-2,6-dichloro-9-[(4-methylphenyl)methyl]-9H-purine
• 英文别名: 8-Bromo-2,6-dichloro-9-[(4-methylphenyl)methyl]purine
• CAS: 1246307-22-1
• 化学式: C₁₃H₉BrCl₂N₄
• 分子量: 372.051
• InChiKey: LDMFWDVXKRYROJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-dichloro-9-(4-methylphenylmethyl)-9H-purine 在 lithium diisopropyl amide 、 1,2-二溴四氯乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.34h， 以75%的产率得到8-bromo-2,6-dichloro-9-[(4-methylphenyl)methyl]-9H-purine
  参考文献：
  名称：

  Synthesis of 8-Bromo-N-benzylpurines via 8-Lithiated Purines: Scope and Limitations

  摘要：

  9-Benzylpurines have been lithiated in the 8-position and subsequently brominated when trapped with BrCCl2CCl2Br. The 8-bromopurines were isolated in excellent yields when the benzyl group carried an alkoxy or alkyl group in the ortho or para position. Without these substituents, the conversion was generally less, and formation of 8,8'-purinyl dimers was observed. There was also evidence of debenzylation in some instances. Bromination of 7-benzylpurines employing the same set of reaction conditions has also been achieved.

  DOI：

  10.1080/00397910903318708

文献信息

• Synthesis of 8-Bromo-<i>N</i>-benzylpurines via 8-Lithiated Purines: Scope and Limitations
  作者：Thywill Gamadeku、Lise-Lotte Gundersen

  DOI：10.1080/00397910903318708

  日期：2010.8.16

  9-Benzylpurines have been lithiated in the 8-position and subsequently brominated when trapped with BrCCl2CCl2Br. The 8-bromopurines were isolated in excellent yields when the benzyl group carried an alkoxy or alkyl group in the ortho or para position. Without these substituents, the conversion was generally less, and formation of 8,8'-purinyl dimers was observed. There was also evidence of debenzylation in some instances. Bromination of 7-benzylpurines employing the same set of reaction conditions has also been achieved.