4-hydroxy-6-methyl-3-(1-(2-(4-phenylthiazol-2-yl)hydrazono)ethyl)-2H-pyran-2-one | 151504-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-6-methyl-3-(1-(2-(4-phenylthiazol-2-yl)hydrazono)ethyl)-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-methyl-3-[C-methyl-N-[(4-phenyl-1,3-thiazol-2-yl)amino]carbonimidoyl]pyran-2-one
• CAS: 151504-48-2
• 化学式: C₁₇H₁₅N₃O₃S
• 分子量: 341.39
• InChiKey: JRTFHZCWCWWGJO-UHFFFAOYSA-N

物化性质

• 沸点：
  510.9±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methyl-3-(1-(2-(4-phenylthiazol-2-yl)hydrazono)ethyl)-2H-pyran-2-one 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.92h， 生成 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 作用下， 以 乙醇 为溶剂， 生成 4-hydroxy-6-methyl-3-(1-(2-(4-phenylthiazol-2-yl)hydrazono)ethyl)-2H-pyran-2-one
  参考文献：
  名称：

  某些1-（4-芳基噻唑-2-基）-1'-（芳基/杂芳基）-3,3'-二甲基-[4,5'-bi-1H-吡唑] -5-醇的合成及抗菌性能

  摘要：

  一系列十六个1-（4-芳基噻唑-2-基）-1'-（芳基/杂芳基）-3,3'-二甲基-[4,5'-bi-1 H-吡唑] -5-醇（由脱氢乙酸（DHA，1）起始，通过逐步形成硫代半脲（2），3-（1-（2-（4-芳基噻唑-2-基）肼基）乙基）-4-羟基合成7a – p） -6-甲基-2 H-吡喃-2-酮（4a – d）和1-（1-（4-芳基噻唑-2-基）-5-羟基-3-甲基-1 H-吡唑-4-基）1,3-丁烷（5a – d）的高收率。研究了合成的联吡唑7a – p对两种革兰氏阳性细菌菌株的体外抗菌和抗真菌活性。枯草芽孢杆菌（MTCC 441）和金黄色葡萄球菌（MTCC 7443），一种革兰氏阴性细菌菌株，即。大肠杆菌（MTCC 42）和两种真菌菌株，即。白色念珠菌（MTCC 183）和黑曲霉（MTCC 282）。发现化合物7a和7e比参考氟康唑表现出更好的针对黑曲霉的抑制活性。此外，标题化合物

  DOI：

  10.2298/jsc160310002m

文献信息

• Synthesis and antimicrobial evaluation of some 1-(4-arylthiazol-2-yl)-1′-(aryl/heteroaryl)-3,3′-dimethyl-[4,5′-bi-1H-pyrazol]-5-ols
  作者：Satbir Mor、Rajni Mohil、Savita Nagoria、Ashwani Kumar

  DOI：10.2298/jsc160310002m

  日期：——

  A series of sixteen 1-(4-arylthiazol-2-yl)-1′-(aryl/heteroaryl)-3,3′-di­methyl-[4,5′-bi-1 H- pyrazol]-5-ols ( 7a – p ) was synthesized starting from dehyd­roacetic acid (DHA, 1 ) via the stepwise formation of thiosemicarbazone ( 2 ), 3-(1-(2-(4-arylthiazol-2-yl)hydrazono)ethyl)-4-hydroxy-6-methyl-2 H -pyran- 2-ones ( 4a – d ) and 1-(1-(4-arylthiazol-2-yl)-5-hydroxy-3-methyl-1 H -pyrazol-4-yl)butane-1

  一系列十六个1-（4-芳基噻唑-2-基）-1'-（芳基/杂芳基）-3,3'-二甲基-[4,5'-bi-1 H-吡唑] -5-醇（由脱氢乙酸（DHA，1）起始，通过逐步形成硫代半脲（2），3-（1-（2-（4-芳基噻唑-2-基）肼基）乙基）-4-羟基合成7a – p） -6-甲基-2 H-吡喃-2-酮（4a – d）和1-（1-（4-芳基噻唑-2-基）-5-羟基-3-甲基-1 H-吡唑-4-基）1,3-丁烷（5a – d）的高收率。研究了合成的联吡唑7a – p对两种革兰氏阳性细菌菌株的体外抗菌和抗真菌活性。枯草芽孢杆菌（MTCC 441）和金黄色葡萄球菌（MTCC 7443），一种革兰氏阴性细菌菌株，即。大肠杆菌（MTCC 42）和两种真菌菌株，即。白色念珠菌（MTCC 183）和黑曲霉（MTCC 282）。发现化合物7a和7e比参考氟康唑表现出更好的针对黑曲霉的抑制活性。此外，标题化合物
• Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles
  作者：Satbir Mor、Rajni Mohil、Devinder Kumar、Munish Ahuja

  DOI：10.1007/s00044-011-9859-y

  日期：2012.11

  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.