5-bromo-1-(1,1-dioxothietan-3-yl)-2-methyl-4-nitroimidazole | 1616388-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-bromo-1-(1,1-dioxothietan-3-yl)-2-methyl-4-nitroimidazole
• 英文别名: 3-(5-bromo-2-methyl-4-nitroimidazol-1-yl)thietane 1,1-dioxide
• CAS: 1616388-95-4
• 化学式: C₇H₈BrN₃O₄S
• 分子量: 310.128
• InChiKey: OIQHPFCYWMCZHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-bromo-2-methyl-4-nitro-1-(thietan-3-yl)-1H-imidazole 在 双氧水 、 溶剂黄146 作用下， 反应 0.33h， 以75%的产率得到5-bromo-1-(1,1-dioxothietan-3-yl)-2-methyl-4-nitroimidazole
  参考文献：
  名称：

  Oxidation and isomerism of thietane-containing heterocycles

  摘要：

  Oxidation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione, 5(6)-nitro-1-(thiethan-3-yl)-benzimidazole, 2-methyl-4-nitro-1-(thiethan-3-yl)- and 5-bromo-2-methyl-4-nitro-1-(thiethan-3-yl)imidazoles was examined. Corresponding 1-oxothietan-3-yl- and 1,1-dioxothietan-3-yl derivatives were synthesized for the first time. Some factors affecting the quality of the final products and optimal conditions of the oxidation of thietanyl derivatives of pyrimidine-2,4(1H,3H)-dione, nitrobenzimidazole, and nitroimidazole were found. According to 1H NMR spectroscopy data, the obtained sulfoxides are mixtures of cis/trans isomers, the diastereomers ratio determined by the substituent at position 3 of thietane ring.

  DOI：

  10.1134/s1070363214050144