ethyl (2E)-2-fluoro-5-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)pent-2-enoate | 812675-86-8

• 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 (2E)-2-fluoro-5-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)pent-2-enoate
• CAS: 812675-86-8
• 化学式: C₁₀H₁₃FN₂O₄
• 分子量: 244.223
• InChiKey: OJBZROQEEQXSQQ-VMPITWQZSA-N

物化性质

• 沸点：
  311.8±52.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.33
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (2E)-2-fluoro-5-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)pent-2-enoate 在 四溴化碳 、 Ph₃P-polymer 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 4-[(3E)-5-bromo-4-fluoropent-3-enyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one
  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：

  2-氟-2-磷酰基乙酸三乙酯 、 3-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)propanal 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 以47.9 g的产率得到ethyl (2E)-2-fluoro-5-(3-methyl-5-oxo-1,2,4-oxadiazol-4(5H)-yl)pent-2-enoate
  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