1-(1,1-dioxothietan-3-yl)-2-methyl-4-nitro-imidazole | 1616388-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1,1-dioxothietan-3-yl)-2-methyl-4-nitro-imidazole
• 英文别名: 1-(1,1-dioxidothietan-3-yl)-2-methyl-4-nitro-1H-imidazole；3-(2-methyl-4-nitroimidazol-1-yl)thietane 1,1-dioxide
• CAS: 1616388-94-3
• 化学式: C₇H₉N₃O₄S
• 分子量: 231.232
• InChiKey: XJQUOZMYNSCSGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 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：

  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68%的产率得到1-(1,1-dioxothietan-3-yl)-2-methyl-4-nitro-imidazole
  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

文献信息

• Dioxothietanylation of heterocycles 2*. Imidazoles and benzimidazoles
  作者：Nadezhda N. Makarova、Elena E. Klen、Ferkat А. Khaliullin

  DOI：10.1007/s10593-019-02543-0

  日期：2019.9

  1-Dioxidothietan-3-yl)-1H-imidazoles and 1-(1,1-dioxidothietan-3-yl)-1H-benzimidazoles were synthesized in the reaction of 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole with the sodium salts of imidazoles and benzimidazoles. The reaction involves addition of azoles to thiete 1,1-dioxide formed in situ, which acts as a Michael acceptor. The effect of pKa values of imidazoles and benzimidazoles

  在3,5-dibromo-1反应中合成了1-（1,1-Dioxidothietan-3-yl）-1 H-咪唑和1-（1,1-dioxidothietan-3-yl）-1 H-苯并咪唑-（1,1-二氧噻吩-3-基）-1 H -1,2,4-三唑与咪唑和苯并咪唑的钠盐。该反应涉及将唑类添加到就地形成的1,1-二氧化噻吩中，该噻吩充当迈克尔受体。显示了咪唑和苯并咪唑的p K a值对其反应性的影响。