5-ethyl-4-methyl-isoxazol-3-one | 51671-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-ethyl-4-methyl-isoxazol-3-one
• 英文别名: 3-Hydroxy-4-methyl-5-ethylisoxazol；3(2H)-Isoxazolone, 5-ethyl-4-methyl-；5-ethyl-4-methyl-1,2-oxazol-3-one
• CAS: 51671-62-6
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: QHXPWCXIEAGWMA-UHFFFAOYSA-N

物化性质

• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-ethyl-4-methyl-isoxazol-3-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 、 乙醚 、 乙醇 为溶剂， 反应 8.33h， 生成 (RS)-ethyl α-(ethoxycarbonyl)-α-(acetylamino)-β-methyl-3-methoxy-4-methylisoxazole-5-propionate
  参考文献：
  名称：

  Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors

  摘要：

  The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) to rat brain synaptic membranes. These data were compared with the earlier reported effects of the compounds on single neurons in the feline spinal cord obtained by microelectrophoretic techniques. The three compounds AMPA, ATPA, and ABPA are agonists at the class of receptors assumed to represent a subtype of physiological (S)-glutamic acid (Glu) receptors. Inhibition of [3H]AMPA binding by ATPA was 1 order of magnitude weaker than that of AMPA, in agreement with the relative potency of these compounds in vivo. ABPA proved to be equipotent with AMPA both as an inhibitor of AMPA binding and as a neuronal excitant. The compounds 8, 15a, and 15b have no effect as inhibitors of AMPA binding, in agreement with in vivo studies that have shown that 8 does not affect the firing of central neurons whereas 15a and 15b are antagonists at NMDA receptors, a subpopulation of excitatory receptors not affected by AMPA. Molecular mechanical calculations on AMPA, ATPA, and ABPA using the program MM2 showed that conformations of AMPA, ABPA, and especially ATPA by rotation of the amino acid side chain have energy barriers. A possible receptor-active conformation is suggested.

  DOI：

  10.1021/jm50001a022
• 作为产物：
  描述：

  2-甲基-3-氧代戊酸乙酯 在 sodium hydroxide 、 盐酸羟胺 作用下， 生成 5-ethyl-4-methyl-isoxazol-3-one 、 3-Ethyl-4-methylisoxazolin-5-on
  参考文献：
  名称：

  Organic Hydroxylamine Derivatives. VII. Isoxazolin-5-ones. An Investigation of a Reaction Sequence Previously Stated to Give 3-Hydroxyisoxazoles.

  摘要：

  DOI：

  10.3891/acta.chem.scand.27-2802

文献信息

• US8466148B2
  申请人：——

  公开号：US8466148B2

  公开（公告）日：2013-06-18
• US9265767B2
  申请人：——

  公开号：US9265767B2

  公开（公告）日：2016-02-23
• Organic Hydroxylamine Derivatives. VII. Isoxazolin-5-ones. An Investigation of a Reaction Sequence Previously Stated to Give 3-Hydroxyisoxazoles.
  作者：Povl Krogsgaard-Larsen、Søren Brøgger Christensen、Hans Hjeds、Jon Songstad、A. Hugh Norbury、Carl-Gunnar Swahn

  DOI：10.3891/acta.chem.scand.27-2802

  日期：——
• Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors
  作者：Jørn Lauridsen、Tage Honoré、Povl Krogsgaard-Larsen

  DOI：10.1021/jm50001a022

  日期：1985.5

  The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) to rat brain synaptic membranes. These data were compared with the earlier reported effects of the compounds on single neurons in the feline spinal cord obtained by microelectrophoretic techniques. The three compounds AMPA, ATPA, and ABPA are agonists at the class of receptors assumed to represent a subtype of physiological (S)-glutamic acid (Glu) receptors. Inhibition of [3H]AMPA binding by ATPA was 1 order of magnitude weaker than that of AMPA, in agreement with the relative potency of these compounds in vivo. ABPA proved to be equipotent with AMPA both as an inhibitor of AMPA binding and as a neuronal excitant. The compounds 8, 15a, and 15b have no effect as inhibitors of AMPA binding, in agreement with in vivo studies that have shown that 8 does not affect the firing of central neurons whereas 15a and 15b are antagonists at NMDA receptors, a subpopulation of excitatory receptors not affected by AMPA. Molecular mechanical calculations on AMPA, ATPA, and ABPA using the program MM2 showed that conformations of AMPA, ABPA, and especially ATPA by rotation of the amino acid side chain have energy barriers. A possible receptor-active conformation is suggested.