1-(2-phenylsulfonylethyl)-7-(2,4-dimethoxybenzyl)-3,7-dihydropurine-2,6-dione | 1000401-00-2

• 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: 1-(2-phenylsulfonylethyl)-7-(2,4-dimethoxybenzyl)-3,7-dihydropurine-2,6-dione
• 英文别名: 1-[2-(benzenesulfonyl)ethyl]-7-[(2,4-dimethoxyphenyl)methyl]-3H-purine-2,6-dione
• CAS: 1000401-00-2
• 化学式: C₂₂H₂₂N₄O₆S
• 分子量: 470.506
• InChiKey: UPECIPZXPSQCRF-UHFFFAOYSA-N

物化性质

• 熔点：
  218 °C(Solvent: Dichloromethane ; Hexane)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-phenylsulfonylethyl)-7-(2,4-dimethoxybenzyl)-3,7-dihydropurine-2,6-dione 、 N-(3-溴丙基)苯二胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以97%的产率得到1-(2-phenylsulfonylethyl)-7-(2,4-dimethoxybenzyl)-3-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-propyl]-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

  摘要：

  An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.067
• 作为产物：
  描述：

  3-allyloxymethyl-1-(2-phenylsulfonylethyl)-7-(2,4-dimethoxybenzyl)-3,7-dihydropurine-2,6-dione 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到1-(2-phenylsulfonylethyl)-7-(2,4-dimethoxybenzyl)-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

  摘要：

  An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.067

文献信息

• Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy
  作者：Matthew B. Allwood、Booma Cannan、Daan M.F. van Aalten、Ian M. Eggleston

  DOI：10.1016/j.tet.2007.09.067

  日期：2007.12

  An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.