9-[(4-Methylphenyl)methyl]-N-prop-2-ynylpurin-6-amine

• 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: 9-[(4-Methylphenyl)methyl]-N-prop-2-ynylpurin-6-amine
• 化学式: C₁₆H₁₅N₅
• 分子量: 277.32
• InChiKey: OBUBAEYJFTVKLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[(4-Methylphenyl)methyl]-N-prop-2-ynylpurin-6-amine 在 四丁基溴化铵 、 caesium carbonate 、 copper(I) bromide 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以80%的产率得到7-methyl-3-(4-methylbenzyl)-3H-imidazo[2,1-i]purine
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular Cyclization ofN-Propargyl-Adenine: Synthesis of Purine-Fused Tricyclics

  摘要：

  A novel protocol to construct fluorescent purine-fused tricyclic products via intramolecular cyclization of N-propargyl-adenine has been developed. With CuBr as the catalyst, a series of purine-fused tricyclic products were obtained in good to excellent yields (19 examples, 75-89% yields). When R-2 was a hydrogen atom in N-propargyl-adenines, the reactions only afforded the endocyclic double bond products. When R-2 was an aryl group, the electron-onating groups favored the endocyclic double bond products, while the electron-withdrawing groups favored the exocyclic double bond products.

  DOI：

  10.1021/jo5001687
• 作为产物：
  描述：

  6-chloro-9-(4-methylbenzyl)-9H-purine 、 炔丙胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 9-[(4-Methylphenyl)methyl]-N-prop-2-ynylpurin-6-amine
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular Cyclization ofN-Propargyl-Adenine: Synthesis of Purine-Fused Tricyclics

  摘要：

  A novel protocol to construct fluorescent purine-fused tricyclic products via intramolecular cyclization of N-propargyl-adenine has been developed. With CuBr as the catalyst, a series of purine-fused tricyclic products were obtained in good to excellent yields (19 examples, 75-89% yields). When R-2 was a hydrogen atom in N-propargyl-adenines, the reactions only afforded the endocyclic double bond products. When R-2 was an aryl group, the electron-onating groups favored the endocyclic double bond products, while the electron-withdrawing groups favored the exocyclic double bond products.

  DOI：

  10.1021/jo5001687

文献信息

• Copper-Catalyzed Intramolecular Cyclization of<i>N</i>-Propargyl-Adenine: Synthesis of Purine-Fused Tricyclics
  作者：Ren-Long Li、Lei Liang、Ming-Sheng Xie、Gui-Rong Qu、Hong-Ying Niu、Hai-Ming Guo

  DOI：10.1021/jo5001687

  日期：2014.4.18

  A novel protocol to construct fluorescent purine-fused tricyclic products via intramolecular cyclization of N-propargyl-adenine has been developed. With CuBr as the catalyst, a series of purine-fused tricyclic products were obtained in good to excellent yields (19 examples, 75-89% yields). When R-2 was a hydrogen atom in N-propargyl-adenines, the reactions only afforded the endocyclic double bond products. When R-2 was an aryl group, the electron-onating groups favored the endocyclic double bond products, while the electron-withdrawing groups favored the exocyclic double bond products.