3-bromo-1-(1,1-dioxothietan-3-yl)-5-phenoxy-1H-1,2,4-triazole | 1425223-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-1-(1,1-dioxothietan-3-yl)-5-phenoxy-1H-1,2,4-triazole
• 英文别名: 3-Bromo-1-(1,1-dioxothietan-3-yl)-5-phenoxy-1 h-1,2,4-triazole；3-(3-bromo-5-phenoxy-1,2,4-triazol-1-yl)thietane 1,1-dioxide
• CAS: 1425223-00-2
• 化学式: C₁₁H₁₀BrN₃O₃S
• 分子量: 344.189
• InChiKey: UGZZEATZXYCQJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 3-bromo-1-(1,1-dioxothietan-3-yl)-5-phenoxy-1H-1,2,4-triazole 在 sodium 作用下， 反应 0.5h， 以36%的产率得到3-bromo-5-phenoxy-1H-1,2,4-triazole
  参考文献：
  名称：

  Thietanyl Protection in the Synthesis of 5-Aryloxy(sulfonyl)-3-bromo-1,2,4-triazoles

  摘要：

  Previously unknown 5-aryloxy- and 5-benzenesulfonyl-3-bromo-1H-1,2,4-triazoles have been synthesized starting from 3,5-dibromo-1,2,4-triazole by successive alkylation with 2-chloromethylthiirane, nucleophilic substitution of the 5-bromine atom by phenoxy or phenylsulfanyl group, oxidation of the thietane sulfur atom with hydrogen peroxide, and removal of the thietanyl protecting group by treatment with sodium ethoxide.

  DOI：

  10.1134/s1070428018120242
• 作为产物：
  描述：

  3-Bromo-1-(thietan-3-yl)-5-phenoxy-1,2,4-triazole 在 双氧水 作用下， 生成 3-bromo-1-(1,1-dioxothietan-3-yl)-5-phenoxy-1H-1,2,4-triazole
  参考文献：
  名称：

  Thietanyl Protection in the Synthesis of 5-Aryloxy(sulfonyl)-3-bromo-1,2,4-triazoles

  摘要：

  Previously unknown 5-aryloxy- and 5-benzenesulfonyl-3-bromo-1H-1,2,4-triazoles have been synthesized starting from 3,5-dibromo-1,2,4-triazole by successive alkylation with 2-chloromethylthiirane, nucleophilic substitution of the 5-bromine atom by phenoxy or phenylsulfanyl group, oxidation of the thietane sulfur atom with hydrogen peroxide, and removal of the thietanyl protecting group by treatment with sodium ethoxide.

  DOI：

  10.1134/s1070428018120242

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.