5-bromo-3-(piperidin-1-yl)-1,2,4-triazole | 1181206-95-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-bromo-3-(piperidin-1-yl)-1,2,4-triazole
• 英文别名: 5-bromo-3-(piperidin-1-yl)-1H-1,2,4-triazole；3-Bromo-5-piperidino-1h-1,2,4-triazole；1-(5-bromo-1H-1,2,4-triazol-3-yl)piperidine
• CAS: 1181206-95-0
• 化学式: C₇H₁₁BrN₄
• 分子量: 231.095
• InChiKey: GLXDQMOFBZYNTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dibromo-1-(1,1-dioxothietan-3-yl)-1H-1,2,4-triazole 、 5-bromo-3-(piperidin-1-yl)-1,2,4-triazole 在 sodium 、 叔丁醇 作用下， 反应 2.0h， 生成 3-bromo-1-(1,1-di-oxothietan-3-yl)-5-(piperidin-1-yl)-1H-1,2,4-triazole 、 5-bromo-1-(1,1-dioxothietan-3-yl)-3-(piperidin-1-yl)-1H-1,2,4-triazole
  参考文献：
  名称：

  Dioxothietanylation of Heterocycles 1. N-(1,1-Dioxothietan-3-yl)-1,2,4-triazoles

  摘要：

  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.

  DOI：

  10.1007/s10593-013-1159-7
• 作为产物：
  描述：

  乙醇 、 3-bromo-1-(1,1-di-oxothietan-3-yl)-5-(piperidin-1-yl)-1H-1,2,4-triazole 在 sodium 作用下， 反应 0.5h， 以84%的产率得到5-bromo-3-(piperidin-1-yl)-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

• Reactions of 1,2,4-triazole derivatives with a “model” thiirane
  作者：E. E. Klen、F. A. Khaliullin

  DOI：10.1134/s1070428010050155

  日期：2010.5

  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.