7-[(3,5-dibromo-1H-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydrothiazolo[2,3-f]purine-2,4(1H,3H)-dione | 1237791-74-0

• 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: 7-[(3,5-dibromo-1H-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydrothiazolo[2,3-f]purine-2,4(1H,3H)-dione
• 英文别名: 7-[(3,5-dibromo-1H-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-dione；7-[(3,5-Dibromo-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydrothiazolo[2,3-f]purine-2,4(1h,3h)-dione；7-[(3,5-dibromo-1,2,4-triazol-1-yl)methyl]-2,4-dimethyl-7,8-dihydropurino[8,7-b][1,3]thiazole-1,3-dione
• CAS: 1237791-74-0
• 化学式: C₁₂H₁₁Br₂N₇O₂S
• 分子量: 477.139
• InChiKey: KSVSUEAPLABFOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  哌啶 、 7-[(3,5-dibromo-1H-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydrothiazolo[2,3-f]purine-2,4(1H,3H)-dione 以 正丁醇 为溶剂， 反应 5.0h， 以95%的产率得到7-[(3-bromo-5-piperidin-1-yl-1H-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydro[1,3]thiazolo[2,3-f]purine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Reactions of 1,2,4-triazole derivatives with a “model” thiirane

  摘要：

  Reactions of 3-mono- and 3,5-disubstituted 1,2,4-triazoles with a "model" thiirane, 8-bromo-1,3-dimethyl-7-(thiiran-2-ylmethyl)-3,7-dihydro-1H-purine-2,6-diones proceed at the positions N(1) and N(2) of the triazole ring and yield 7-(5-R-3-R'-1,2,4-triazol-1-yl)methyl- and/or 7-(5-R'-3-R-1,2,4-triazol-1-yl)methyl-1,3-dimethyl-6,7-dihydro[1,3]thiazolo[2,3-f]-purine-2,4-(1H,3H)-diones. 3-Methylsulfonyl-1,2,4-triazole reacted regiospecifically at the position N(1) forming 1,3-dimethyl-7-[(3-methyl-sulfonyl-1,2,4-triazole-1-yl)-methyl]-6,7-dihydro[1,3]thiazolo-[2,3-f]purine-2,4(1H,3H)-dione.

  DOI：

  10.1134/s1070428010050155
• 作为产物：
  描述：

  8-Bromo-1,3-dimethyl-7-(2,3-epithiopropyl)xanthine 、 3,5-二溴-1,2,4-三氮唑 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到7-[(3,5-dibromo-1H-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydrothiazolo[2,3-f]purine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Reactions of 1,2,4-triazole derivatives with a “model” thiirane

  摘要：

  Reactions of 3-mono- and 3,5-disubstituted 1,2,4-triazoles with a "model" thiirane, 8-bromo-1,3-dimethyl-7-(thiiran-2-ylmethyl)-3,7-dihydro-1H-purine-2,6-diones proceed at the positions N(1) and N(2) of the triazole ring and yield 7-(5-R-3-R'-1,2,4-triazol-1-yl)methyl- and/or 7-(5-R'-3-R-1,2,4-triazol-1-yl)methyl-1,3-dimethyl-6,7-dihydro[1,3]thiazolo[2,3-f]-purine-2,4-(1H,3H)-diones. 3-Methylsulfonyl-1,2,4-triazole reacted regiospecifically at the position N(1) forming 1,3-dimethyl-7-[(3-methyl-sulfonyl-1,2,4-triazole-1-yl)-methyl]-6,7-dihydro[1,3]thiazolo-[2,3-f]purine-2,4(1H,3H)-dione.

  DOI：

  10.1134/s1070428010050155

文献信息

• Reactions of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4-triazole with NH-azoles
  作者：F. A. Khaliullin、E. E. Klen、N. Yu. Makarova、A. G. Pestrikova

  DOI：10.1134/s1070428014020213

  日期：2014.2

  Reactions of 3,5-dibromo-1-(thiiran-2-ylmethyl)-1,2,4-triazole with 3,5-dimethylpyrazole, 1,3-dimethyl-3,7-dihydropurine-2,6-dione, 3,5-dibromo-1,2,4-triazole, 2,4,5-tribromoimidazole, and 2-chlorobenzimidazole lead to the formation of 5-azolylmethyl-2-bromo-5,6-dihydrothiazolo[3,2-b]-1,2,4-triazoles. In the case of 8-bromo-1,3-dimethyl-3,7-dihydropurine-2,6-dione the intermediate thiolate anion undergoes cyclization into 7-[(3,5-dibromo-1,2,4-triazol-1-yl)methyl]-1,3-dimethyl-6,7-dihydrothiazolo[2,3-f]purine-2,4(1H,3H)-dione. The structure of reaction products depends on the relative rate of substitution of leaving groups in the reagents.