ethyl 3-hydroxymethyl-5-methyl-4-isoxazolecarboxylate | 95104-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-hydroxymethyl-5-methyl-4-isoxazolecarboxylate
• 英文别名: ethyl 3-(hydroxymethyl)-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 95104-47-5
• 化学式: C₈H₁₁NO₄
• mdl: MFCD25969472
• 分子量: 185.18
• InChiKey: YEJLCENFADMRTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxymethyl-5-methyl-4-isoxazolecarboxylate 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (E)-4-Ethoxycarbonyl-5-methyl-3-(2-phenylethen-1-yl)isoxazole
  参考文献：
  名称：

  An alternative isoxazole route to α-alkoxycarbonyl-β-diketones

  摘要：

  Cycloaddition of oxygen-functionalized nitrile oxides to the enamine from ethyl acetoacetate produces 4-ethoxycarbonyl-5-methylisoxazoles carrying a 3-tetrahydropyranyloxymethyl, 3-diethoxymethyl or 3-ethoxycarbonyl substituent; the 3-formylisoxazole is prepared from the former two and condensed in situ with phosphoranes to give 3-alkenylisoxazoles that are cleaved by hexacarbonylmolybdenum or hydrogenolysis to afford alpha-alkoxycarbonyl-beta-diketones.

  DOI：

  10.1039/p19960001319
• 作为产物：
  描述：

  (E)-3-(1-吡咯烷酮)巴豆酸乙酯 在 甲醇 、 amberlyst-15 、 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 ethyl 3-hydroxymethyl-5-methyl-4-isoxazolecarboxylate
  参考文献：
  名称：

  An alternative isoxazole route to α-alkoxycarbonyl-β-diketones

  摘要：

  Cycloaddition of oxygen-functionalized nitrile oxides to the enamine from ethyl acetoacetate produces 4-ethoxycarbonyl-5-methylisoxazoles carrying a 3-tetrahydropyranyloxymethyl, 3-diethoxymethyl or 3-ethoxycarbonyl substituent; the 3-formylisoxazole is prepared from the former two and condensed in situ with phosphoranes to give 3-alkenylisoxazoles that are cleaved by hexacarbonylmolybdenum or hydrogenolysis to afford alpha-alkoxycarbonyl-beta-diketones.

  DOI：

  10.1039/p19960001319

文献信息

• Ionotropic excitatory amino acid receptor ligands. Synthesis and pharmacology of a new amino acid AMPA antagonist
  作者：U Madsen

  DOI：10.1016/s0223-5234(00)00104-5

  日期：2000.1

  We have previously described the potent and selective (RS)-2-amino-3-(3-hydroxy-5-methyl-5-isoxazolyl)propionic acid (AMPA) receptor agonist, (RS)-2-amino-3-(3-carboxy-5-merhyl-4-isoxazolyl)propionic acid (ACPA), and the AMPA receptor antagonist (RS)-2-amino3-[3-(carboxymethoxy)-5-methyl-4-isoxazolyl]propionic acid (AMOA). Using these AMPA receptor ligands as leads, a series of compounds have been developed as tools for further elucidation of the structural requirements for activation and blockade of AMPA receptors. The synthesized compounds have been tested for activity at ionotropic excitatory amino acid (EAA) receptors using receptor binding and electrophysiological techniques, and for activity at metabotropic EAA receptors using second messenger assays. Compounds 1 and 4 were essentially inactive. (RS)-2-Amino-3-[3-(2-carboxyethyl)-5-methyl-4-isoxazoly]propionic acid (ACMP, 2), on the other hand, was shown to be a selective AMPA receptor antagonist (IC50 = 73 mu M), more potent in electrophysiological experiments than AMOA (IC50 = 320 mu M). The isomeric analogue of 2, compound 5, did not show AMPA antagonist effects, but was a weak NMDA receptor antagonist (IC50 = 540 mu M). Finally, compound 3, which is an isomer of ACPA, turned out to be a very weak NMDA antagonist, and an AMPA receptor agonist approximately 1 000 times weaker than ACPA. None of the compounds showed agonist or antagonist effects at metabotropic EAA receptors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Synthesis of Some Ethyl 3-Substituted-5-(1-hydroxyalkyl)-isoxazole-4-carboxylates from 4-Ethoxycarbonyl-3(2<i>H</i>)-furanones
  作者：Christian Deshayes、Michel Chabannet、Suzanne Gelin

  DOI：10.1055/s-1984-31002

  日期：——
• DESHAYES, CH.;CHABANNET, M.;GELIN, S., SYNTHESIS, BRD, 1984, N 10, 868-870
  作者：DESHAYES, CH.、CHABANNET, M.、GELIN, S.

  DOI：——

  日期：——