3-allyloxymethyl-1-methyl-3,7-dihydropurine-2,6-dione

• 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: 3-allyloxymethyl-1-methyl-3,7-dihydropurine-2,6-dione
• 英文别名: 1-methyl-3-(prop-2-enoxymethyl)-7H-purine-2,6-dione
• 化学式: C₁₀H₁₂N₄O₃
• 分子量: 236.23
• InChiKey: HRLWXEQDCHWNLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-allyloxymethyl-1-methyl-3,7-dihydropurine-2,6-dione 、 3-溴丙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以46%的产率得到3-(3-allyloxymethyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-propionic acid methyl ester
  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-7-(2,4-dimethoxybenzyl)-1-methyl-3,7-dihydropurine-2,6-dione 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到3-allyloxymethyl-1-methyl-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.