ethyl 4-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-3-oxobutanoate | 812675-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 4-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-3-oxobutanoate
• 英文别名: Ethyl 4-(3-methyl-5-oxo-1,2,4-oxadiazol-4-yl)-3-oxobutanoate；ethyl 4-(3-methyl-5-oxo-1,2,4-oxadiazol-4-yl)-3-oxobutanoate
• CAS: 812675-81-3
• 化学式: C₉H₁₂N₂O₅
• 分子量: 228.205
• InChiKey: WLDLRZHILTULPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-3-oxobutanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 ethyl (2-methyl-1H-imidazol-5-yl)acetate
  参考文献：
  名称：

  3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines

  摘要：

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.030
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 3-methyl-[1,2,4]oxadiazol-5-one potassium salt 在 caesium carbonate 、 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以58%的产率得到ethyl 4-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)-3-oxobutanoate
  参考文献：
  名称：

  3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines

  摘要：

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.030

文献信息

• 3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines
  作者：Alan E. Moormann、Jane L. Wang、Katherine E. Palmquist、Michele A. Promo、Jeffery S. Snyder、Jeffrey A. Scholten、Mark A. Massa、James A. Sikorski、R. Keith Webber

  DOI：10.1016/j.tet.2004.09.030

  日期：2004.11

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.