8-bromo-7-(thietanyl-3)xanthine | 1236768-73-2

• 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: 8-bromo-7-(thietanyl-3)xanthine
• 英文别名: 8-bromo-1-butyl-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
• CAS: 1236768-73-2
• 化学式: C₁₃H₁₇BrN₄O₂S
• 分子量: 373.274
• InChiKey: DMDYHRRAJHRTFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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-7-(thietanyl-3)xanthine 、 N,N-二甲基甲酰胺 在 三羟甲基氨基甲烷 作用下， 反应 1.0h， 以90%的产率得到1-butyl-8-(dimethylamino)-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  Unusual Reaction of 8-Bromo-3-methyl-7-(thietan-3-yl)3,7-dihydro-1H-purine-2,6-diones with Trisamine in Dimethylformamide

  摘要：

  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.

  DOI：

  10.1134/s1070428020020049
• 作为产物：
  描述：

  1-碘丁烷 、 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88%的产率得到8-bromo-7-(thietanyl-3)xanthine
  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

• Synthesis and Antidepressant Activity of 8-Amino-Substituted 1-Butyl-3-Methylxanthines Containing a Thietane Ring
  作者：Yu. V. Shabalina、F. A. Khaliullin、I. L. Nikitina、A. F. Miftakhova、R. M. Sharafutdinov

  DOI：10.1007/s11094-020-02114-0

  日期：2020.2

  A series of 8-amino-substituted 1-butyl-3-methylxanthines containing a thietane ring were obtained in 47 – 96% yields by reacting 7-(thietanyl-3)-, 7-(1-oxothietanyl-3)-, and 7-(1,1-dioxothietanyl-3)-8-bromo-1-butyl-3-methylxanthines with piperidine and morpholine. Reaction of 8-amino-substituted 1-butyl-3-methyl-7-(1,1-dioxothietanyl-3)xanthines with sodium ethoxide synthesized 8-amino-substituted 1-butyl-3-methylxanthines in 85 – 98% yields. The structures of the compounds were confirmed by IR and PMR spectroscopy. The synthesized compounds exhibited antidepressant activity.

  将 7-(硫杂环丁烷-3)-、7-(1-氧代硫杂环丁烷-3)-和 7-(1,1-二氧代硫杂环丁烷-3)-8-溴-1-丁基-3-甲基黄嘌呤与哌啶和吗啉反应，得到一系列含有硫杂环的 8-氨基取代的 1-丁基-3-甲基黄嘌呤，产率为 47 - 96%。8- 氨基取代的 1-丁基-3-甲基-7-(1,1-二氧代硫杂环丁烷-3)黄嘌呤与乙醇钠反应合成了 8-氨基取代的 1-丁基-3-甲基黄嘌呤，产率为 85 - 98%。红外光谱和 PMR 光谱证实了这些化合物的结构。合成的化合物具有抗抑郁活性。