5,6-dihydro-11-methylpurino[8,9-a]isoquinoline | 1219139-16-8

• 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: 5,6-dihydro-11-methylpurino[8,9-a]isoquinoline
• 英文别名: 11-Methyl-5,6-dihydropurino[8,9-a]isoquinoline
• CAS: 1219139-16-8
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: NFWBSDBUIMBWAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  9-(2-chlorophenethyl)-6-methyl-9H-purine 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以99%的产率得到5,6-dihydro-11-methylpurino[8,9-a]isoquinoline
  参考文献：
  名称：

  Intramolecular Direct C−H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-f]phenanthridines and 5,6-Dihydropurino[8,9-a]isoquinolines§Dedicated to the memory of Keith Fagnou.

  摘要：

  Intramolecular C-H arylations were employed as a key step in the synthesis of hitherto unknown fused purine systems: 13-substituted purino[8,9-f]phenanthridines and 11-substituted 5,6-dihydropurino[8,9-a]isoquinolines. The purino[8,9-f]phenanthridines were prepared in moderate yields by double C-H arylations of 9-phenylpurines with 1,2-diiodobenzene or, more efficiently, by consecutive Suzuki coupling of 9-(2-bromophenyl)purines with 2-bromophenylboronic acid followed by intramolecular C-H arylation. 5,6-Dihydropurino[8,9-a]isoquinolines were prepared in quantitative yields by intramolecular C-H arylations of 9-(2-chlorophenethyl)purines.

  DOI：

  10.1021/jo100111t

文献信息

• Intramolecular Direct C−H Arylation Approach to Fused Purines. Synthesis of Purino[8,9-<i>f</i>]phenanthridines and 5,6-Dihydropurino[8,9-<i>a</i>]isoquinolines§Dedicated to the memory of Keith Fagnou.
  作者：Igor Čerňa、Radek Pohl、Blanka Klepetářová、Michal Hocek

  DOI：10.1021/jo100111t

  日期：2010.4.2

  Intramolecular C-H arylations were employed as a key step in the synthesis of hitherto unknown fused purine systems: 13-substituted purino[8,9-f]phenanthridines and 11-substituted 5,6-dihydropurino[8,9-a]isoquinolines. The purino[8,9-f]phenanthridines were prepared in moderate yields by double C-H arylations of 9-phenylpurines with 1,2-diiodobenzene or, more efficiently, by consecutive Suzuki coupling of 9-(2-bromophenyl)purines with 2-bromophenylboronic acid followed by intramolecular C-H arylation. 5,6-Dihydropurino[8,9-a]isoquinolines were prepared in quantitative yields by intramolecular C-H arylations of 9-(2-chlorophenethyl)purines.