8-bromo-3-methyl-1-propyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione | 1005482-54-1

• 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-3-methyl-1-propyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione
• 英文别名: 8-bromo-3-methyl-1-propyl-7-(thietan-3-yl)purine-2,6-dione
• CAS: 1005482-54-1
• 化学式: C₁₂H₁₅BrN₄O₂S
• 分子量: 359.247
• InChiKey: SRQDLVWEZGOHPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-bromo-3-methyl-1-propyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以56%的产率得到8-bromo-3-methyl-1-propyl-7-(1,1-dioxo-λ6-thietan-3-yl)-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Thietane ring as a novel protecting group

  摘要：

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.

  DOI：

  10.1134/s1070428009010187
• 作为产物：
  描述：

  8-bromo-3-methyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione 、 1-碘代丙烷 在 氢氧化钾 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以84%的产率得到8-bromo-3-methyl-1-propyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  Thietane ring as a novel protecting group

  摘要：

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.

  DOI：

  10.1134/s1070428009010187

文献信息

• Unusual Reaction of 8-Bromo-3-methyl-7-(thietan-3-yl)3,7-dihydro-1H-purine-2,6-diones with Trisamine in Dimethylformamide
  作者：F. А. Khaliullin、Yu. V. Shabalina

  DOI：10.1134/s1070428020020049

  日期：2020.2

  The reaction of 8-bromo-substituted 3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-purine-2,6-diones with trisamine in DMF gave, instead of the expected 8-tris(hydroxymethyl)methylamino-substituted products, 8-dimethylamino-substituted 3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-purine-2,6-diones. The formation of unusual reaction products was explained by the initial reaction of DMF with trisamine to form dimethylamine and subsequent nucleophilic substitution reaction of the latter with the bromine atom.