8-bromo-3-methyl-1-pentyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione | 1236768-76-5

• 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-pentyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
• 英文别名: 8-bromo-3-methyl-1-pentyl-7-(thietan-3-yl)purine-2,6-dione
• CAS: 1236768-76-5
• 化学式: C₁₄H₁₉BrN₄O₂S
• 分子量: 387.3
• InChiKey: OVMIEEMYWNYQQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.82
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  8-bromo-3-methyl-1-pentyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以52%的产率得到8-bromo-1-butyl-3-methyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
  参考文献：
  名称：

  Thietanyl protection in the synthesis of 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-diones

  摘要：

  The protection of the 7-NH group in 8-bromo-3-methyl-3,7-dihydro-1H-pyrine-2,6-dione during the synthesis of 7-ubsubstituted 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-pyrine-2,6-diones with a thienyl group was applied that was introduced by the reaction with 2-chloromethylthiirane. The thietanyl protection was removed by treating with sodium alcoholate after the oxidation with hydrogen peroxide to thietane 1,1-dioxide group.

  DOI：

  10.1134/s1070428010050167
• 作为产物：
  描述：

  1-溴戊烷 、 8-bromo-3-methyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以77%的产率得到8-bromo-3-methyl-1-pentyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
  参考文献：
  名称：

  Thietanyl protection in the synthesis of 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-diones

  摘要：

  The protection of the 7-NH group in 8-bromo-3-methyl-3,7-dihydro-1H-pyrine-2,6-dione during the synthesis of 7-ubsubstituted 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-pyrine-2,6-diones with a thienyl group was applied that was introduced by the reaction with 2-chloromethylthiirane. The thietanyl protection was removed by treating with sodium alcoholate after the oxidation with hydrogen peroxide to thietane 1,1-dioxide group.

  DOI：

  10.1134/s1070428010050167

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.