8-bromo-1-butyl-3-methyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione | 1236768-74-3

• 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-1-butyl-3-methyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
• 英文别名: 8-bromo-7-(1,1-dioxothietanyl-3)xanthine
• CAS: 1236768-74-3
• 化学式: C₁₃H₁₇BrN₄O₄S
• 分子量: 405.272
• InChiKey: IILTVKJUPTUNPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  23.0
• 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：
  95.96
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  8-bromo-1-butyl-3-methyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione 在 sodium 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 1-butyl-3-methyl-8-(morpholin-4-yl)-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

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

  摘要：

  1-Alkyl-8-bromo-3-methyl-7-(1,1-dioxo-1 lambda(6)-thietan-3-yl)-3,7-dihydro-1H-purine-2,6-diones reacted with amines to give the corresponding 1-alkyl-8-amino-3-methyl-7-(1,1-dioxo-1 lambda(6)-thietan-3-yl)-3,7-dihydro-1H-purine-2,6-diones which were treated with sodium alkoxide to remove thietanyl protecting group with formation of 1-alkyl-8-amino-3-methyl-3,7-dihydro-1H-purine-2,6-diones possessing no substituent on N-7.

  DOI：

  10.1134/s1070428015100139
• 作为产物：
  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

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。