1,3-Butanedione,1-[5-hydroxy-3-methyl-1-(4-phenyl-2-thiazolyl)-1H-pyrazol-4-yl]- | 129302-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Butanedione,1-[5-hydroxy-3-methyl-1-(4-phenyl-2-thiazolyl)-1H-pyrazol-4-yl]-
• 英文别名: 1-<5-hydroxy-3-methyl-1-(4-phenyl-2-thiazolyl)-4-pyrazolyl>-1,3-butanedione；1-(5-hydroxy-3-methyl-1-(4-phenylthiazol-2-yl)-1H-pyrazol-4-yl)butane-1,3-dione
• CAS: 129302-15-4
• 化学式: C₁₇H₁₅N₃O₃S
• 分子量: 341.39
• InChiKey: PAVZVHVWKRKBIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  576.4±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,3-Butanedione,1-[5-hydroxy-3-methyl-1-(4-phenyl-2-thiazolyl)-1H-pyrazol-4-yl]- 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.92h， 以68%的产率得到3-methyl-4-(3-methylisoxazol-5-yl)-1-(4-phenylthiazol-2-yl)-1H-pyrazol-5-ol
  参考文献：
  名称：

  Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles

  摘要：

  A series of isoxazolyl thiazolyl pyrazoles 5a-d was synthesized by multi-step process, starting from 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (dehydroacetic acid, DHAA) 1. DHAA 1 was easily converted to thiosemicarbazone 2 which on reaction with alpha-bromoketones yielded thiazolyl hydrazones 3. Refluxing 3 in ethanol-acetic acid furnished 1-(5-hydroxy-3-methyl-1-substituted pyrazol-4-yl)-1,3-butanediones 4. Finally, the title compounds 5a-d were synthesized from 4 on treatment with hydroxylamine. The in vitro antimicrobial activity of compounds 3a-d, 4a-d and 5a-d were tested. Most of the synthesized compounds exhibited significant antibacterial and antifungal activities.

  DOI：

  10.1007/s00044-011-9859-y
• 作为产物：
  描述：

  去氢乙酸 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 1,3-Butanedione,1-[5-hydroxy-3-methyl-1-(4-phenyl-2-thiazolyl)-1H-pyrazol-4-yl]-
  参考文献：
  名称：

  Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles

  摘要：

  A series of isoxazolyl thiazolyl pyrazoles 5a-d was synthesized by multi-step process, starting from 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (dehydroacetic acid, DHAA) 1. DHAA 1 was easily converted to thiosemicarbazone 2 which on reaction with alpha-bromoketones yielded thiazolyl hydrazones 3. Refluxing 3 in ethanol-acetic acid furnished 1-(5-hydroxy-3-methyl-1-substituted pyrazol-4-yl)-1,3-butanediones 4. Finally, the title compounds 5a-d were synthesized from 4 on treatment with hydroxylamine. The in vitro antimicrobial activity of compounds 3a-d, 4a-d and 5a-d were tested. Most of the synthesized compounds exhibited significant antibacterial and antifungal activities.

  DOI：

  10.1007/s00044-011-9859-y

文献信息

• A Facile Route for the Synthesis of 1-[5-Hydroxy-3-methyl-1-(2-thiazolyl)-4-pyrazolyl]-1,3-butanediones from Dehydroacetic Acid
  作者：S. P. Singh、L. S. Tarar、Devinder Kumar

  DOI：10.1080/00397919308011286

  日期：1993.7

  Abstract Thiosemicarbazone (1) of dehydroacetic acid (DHAA) reacts smoothly with α-haloketones to yield corresponding thiazolylhydrazones (2) of DHAA, which on refluxing in EtOH-AcOH rearrange to the title compounds (3).

  摘要 脱氢乙酸 (DHAA) 的硫缩氨基脲 (1) 与 α-卤代酮顺利反应生成相应的 DHAA 噻唑基腙 (2)，在 EtOH-AcOH 中回流后重排为标题化合物 (3)。