3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1H-1,2,4-triazole | 1083099-14-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1H-1,2,4-triazole
• 英文别名: 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole；3,5-dibromo-1-(1,1-dioxo-λ⁶-thietan-3-yl)-1H-1,2,4-triazole；3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1,2,4-triazole；3-(3,5-dibromo-1,2,4-triazol-1-yl)thietane 1,1-dioxide
• CAS: 1083099-14-2
• 化学式: C₅H₅Br₂N₃O₂S
• 分子量: 330.988
• InChiKey: CQRXLRVMVSYKDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  地巴唑 、 3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1H-1,2,4-triazole 在 sodium 、 叔丁醇 作用下， 反应 2.0h， 以32%的产率得到2-benzyl-1-(1,1-dioxidothietan-3-yl)-1H-benzimidazole
  参考文献：
  名称：

  杂环2 *的二氧杂环丁烷基化。咪唑和苯并咪唑

  摘要：

  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。

  DOI：

  10.1007/s10593-019-02543-0
• 作为产物：
  描述：

  3,5-dibromo-1-(thietan-3-yl)-1,2,4-triazole 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以65%的产率得到3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1H-1,2,4-triazole
  参考文献：
  名称：

  Thietane ring as a novel protecting group

  摘要：

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.

  DOI：

  10.1134/s1070428009010187

文献信息

• Dioxothietanylation of Heterocycles 1. N-(1,1-Dioxothietan-3-yl)-1,2,4-triazoles
  作者：E. E. Klen、N. N. Makarova、F. A. Khaliullin

  DOI：10.1007/s10593-013-1159-7

  日期：2013.1

  3,5-Substituted 1-(1,1-dioxothietan-3-yl)-1,2,4-triazoles have been prepared by treating NH-1,2,4-tri-azole sodium salts with 3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1,2,4-triazole (a novel dioxothietanylating reagent). The reactions occur regioselectively at the position 2 for 5-bromo-1,2,4-triazoles containing ethoxy-, isopropoxy-, or phenoxy groups at the position 3 and at position 1 for 3-methylsulfanyl-1,2,4-tri-azole. The reaction occurs nonselectively at positions 1 and 2 in the case of 3-methylsulfonyl-1,2,4-tri-azole and 5-bromo-3-(piperidin-1-yl)-1,2,4-triazole, to give the isomeric 3-R-5-R-1- and 5-R-3-R-1-1-(1,1-di-oxothietan-3-yl)-1,2,4-triazoles.
• Dioxothietanylation of NH-heterocycles
  作者：E. E. Klen、N. N. Makarova、F. A. Khaliullin

  DOI：10.1007/s10593-011-0791-3

  日期：2011.7
• Thietane ring as a novel protecting group
  作者：F. A. Khaliullin、E. E. Klen

  DOI：10.1134/s1070428009010187

  日期：2009.1

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.
• 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。