2-methyl-5-phenylthiazolecarboxylic acid thiosemicarbazide | 139156-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-5-phenylthiazolecarboxylic acid thiosemicarbazide
• 英文别名: [(2-Methyl-5-phenyl-1,3-thiazole-4-carbonyl)amino]thiourea
• CAS: 139156-71-1
• 化学式: C₁₂H₁₂N₄OS₂
• 分子量: 292.385
• InChiKey: NXIUGEDPMRSIJZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenylthiazolecarboxylic acid thiosemicarbazide 在 sodium hydroxide 作用下， 反应 3.0h， 以67%的产率得到3-(2'-methyl-5'-phenyl-4'-thiazolyl)-4H-5-mercapto-1,2,4-triazole
  参考文献：
  名称：

  Synthesis of novel heterocycles from thiazolecarbohydrazides

  摘要：

  Cyclization of 2-methyl (or -phenyl)-5-phenylthiazole-4-carbohydrazides (1) and (2) under various conditions gives differing oxadiazoles: 2-(2'-substituted-5'-phenyl-4'-thiazolyl)-1,3,4-oxadiazole-5-thiones (7) and (8), and 2-(2'-substituted-5'-phenyl-4'-thiazolyl)-1,3,4-oxadiazoles (9) and (10). Cyclodehydration of thiazolecarbonyl-thiosemicarbazides (3)-(6) with NaOH gives the 3-(2'-substituted-5'-phenyl-4'-thiazolyl)-4-substituted-4H-5-mercapto-1,2,4-triazoles (11)-(14), while H3PO4 gives the 2-(2'-substituted-5-phenyl-4'-thiazolyl)-5-phenylamino-1,3,4-thiadiazoles (15) and (16).

  DOI：

  10.1007/bf00863079
• 作为产物：
  描述：

  methyl 3-phenyl-3-chloro-2-ketopropionate 在 盐酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 2-methyl-5-phenylthiazolecarboxylic acid thiosemicarbazide
  参考文献：
  名称：

  Synthesis of novel thiazoles bearing hydrazine, thiosemicarbazide, thiazole, and thiazolidinone moieties

  摘要：

  Thiazolecarboxylate esters (I) and (II) react with hydrazine hydrate to give the acid hydrazides (III) and (IV), which then react with KSCN and PhNCS to give high yields of the thiosemicarbazides (V) (VIII). Cyclocondensation of the thiosemicarbazide (V) with 3-phenyl-3-chloro-2-oxopropionic acid derivatives gives compounds with two thiazole moieties (IX)-(XIV). The reaction of the phenylthiosemicarbazides (VII) and (VIII) with chloroacetyl chloride and (or) chloroacetic acid affords the thiazolidinonethiazoles (XV) and (XVI).

  DOI：

  10.1007/bf00959725