4-Ethoxycarbonyl-3-formyl-5-methylisoxazole | 180295-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Ethoxycarbonyl-3-formyl-5-methylisoxazole
• 英文别名: Ethyl 3-formyl-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 180295-75-4
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: ODRRWMXSPMBRNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Ethoxycarbonyl-3-formyl-5-methylisoxazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 ethyl 5-methyl-3-[(1Z,3E)-penta-1,3-dienyl]-1,2-oxazole-4-carboxylate
  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 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 生成 4-Ethoxycarbonyl-3-formyl-5-methylisoxazole
  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

• An alternative isoxazole route to α-alkoxycarbonyl-β-diketones
  作者：Raymond C. F. Jones、Stephen H. Dunn、Kathryn A. M. Duller

  DOI：10.1039/p19960001319

  日期：——

  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.