3-Phenyl-3-(2H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid hydrazide | 827607-22-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-Phenyl-3-(2H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid hydrazide
• 英文别名: 3-phenyl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanehydrazide
• CAS: 827607-22-7
• 化学式: C₁₁H₁₃N₅OS
• 分子量: 263.323
• InChiKey: VRIAXECFROJRMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Phenyl-3-(2H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid hydrazide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 5-[2-(1H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis and Transformations of 2-R-5-Aryl-5,6-dihydro-7H-[1,2,4]-triazolo[5,1-b][1,3]thiazin-7-ones

  摘要：

  A new procedure for preparation of 2-R-5-aryl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 5-R-1,2,4-triazole-3-thiones with 3-arylacryloyl chlorides was developed. The thiazine ring of the [ 1,2,4]triazolo-[5,1-b][1,3]thiazin-7-ones is easily cleaved by treating with ammonia and hydrazine affording amides and hydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-yisulfanyl)propanoic acids. The latter react with isothiocyanates furnishing carbamoyl thiohydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-yisulfanyl)propanoic acids that in alkaline media undergo cyclization into 4-aryl-5-[2-(4H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-2,4-dihydro-3H- 1,2,4-triazole-5-thiones.

  DOI：

  10.1023/b:rujo.0000034947.32339.fb
• 作为产物：
  描述：

  5-phenyl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 以83%的产率得到3-Phenyl-3-(2H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid hydrazide
  参考文献：
  名称：

  Synthesis and Transformations of 2-R-5-Aryl-5,6-dihydro-7H-[1,2,4]-triazolo[5,1-b][1,3]thiazin-7-ones

  摘要：

  A new procedure for preparation of 2-R-5-aryl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 5-R-1,2,4-triazole-3-thiones with 3-arylacryloyl chlorides was developed. The thiazine ring of the [ 1,2,4]triazolo-[5,1-b][1,3]thiazin-7-ones is easily cleaved by treating with ammonia and hydrazine affording amides and hydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-yisulfanyl)propanoic acids. The latter react with isothiocyanates furnishing carbamoyl thiohydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-yisulfanyl)propanoic acids that in alkaline media undergo cyclization into 4-aryl-5-[2-(4H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-2,4-dihydro-3H- 1,2,4-triazole-5-thiones.

  DOI：

  10.1023/b:rujo.0000034947.32339.fb

文献信息

• Synthesis and Transformations of 2-R-5-Aryl-5,6-dihydro-7H-[1,2,4]-triazolo[5,1-b][1,3]thiazin-7-ones
  作者：V. N. Britsun、A. N. Esipenko、A. A. Kudryavtsev、M. O. Lozinskii

  DOI：10.1023/b:rujo.0000034947.32339.fb

  日期：2004.2

  A new procedure for preparation of 2-R-5-aryl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 5-R-1,2,4-triazole-3-thiones with 3-arylacryloyl chlorides was developed. The thiazine ring of the [ 1,2,4]triazolo-[5,1-b][1,3]thiazin-7-ones is easily cleaved by treating with ammonia and hydrazine affording amides and hydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-yisulfanyl)propanoic acids. The latter react with isothiocyanates furnishing carbamoyl thiohydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-yisulfanyl)propanoic acids that in alkaline media undergo cyclization into 4-aryl-5-[2-(4H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-2,4-dihydro-3H- 1,2,4-triazole-5-thiones.