5-氨基异噁唑-3-羧酸甲酯 | 1629161-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基异噁唑-3-羧酸甲酯
• 英文名称: methyl 5-aminoisoxazole-3-carboxylate
• 英文别名: 3-methoxycarbonyl-5-aminoisoxazole；Methyl 5-aminoisoxazole-3-carboxylate；methyl 5-amino-1,2-oxazole-3-carboxylate
• CAS: 1629161-40-5
• 化学式: C₅H₆N₂O₃
• mdl: MFCD27923272
• 分子量: 142.114
• InChiKey: ASPWUCLSRISGIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氨基异噁唑-3-羧酸甲酯 在 硝酸铵 、 三氟乙酸酐 作用下， 反应 12.0h， 以70%的产率得到methyl 5-amino-4-nitroisoxazole-3-carboxylate
  参考文献：
  名称：

  5-氨基异恶唑的直接化学选择性4-硝化反应

  摘要：

  带有3-位吸电子基团的5-氨基异恶唑与三氟乙酰硝酸盐（由硝酸铵和三氟乙酸酐生成）发生化学选择性反应，得到相应的4-硝基衍生物，产率高达80％。通过计算研究使结果合理化。几种5-氨基-4-硝基异恶唑-3-羧酸衍生物显示出中等的抗菌活性。

  DOI：

  10.1016/j.mencom.2020.07.027
• 作为产物：
  描述：

  methyl 5-nitroisoxazole-3-carboxylate 在 溶剂黄146 、 锌 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 以73%的产率得到5-氨基异噁唑-3-羧酸甲酯
  参考文献：
  名称：

  Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles

  摘要：

  Reduction by using SnCl2 of easily accessible 5-nitroisoxazoles substituted with an electron-withdrawing group (EWG) has been studied. Whereas the reaction in ethanol yielded 5-aminoisoxazoles, performing the reaction in tetrahydrofuran gave previously unknown 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles. Both reduction procedures were optimized to afford the corresponding products in good to excellent yields. Some mechanistic details concerning the inclusion of the tetrahydrofuranyl moiety into the reaction product are discussed

  DOI：

  10.1055/s-0033-1340827

文献信息

• Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles
  作者：Elena Averina、Dmitry Vasilenko、Yuri Samoilichenko、Yuri Grishin、Victor Rybakov、Tamara Kuznetsova、Nikolay Zefirov

  DOI：10.1055/s-0033-1340827

  日期：——

  Reduction by using SnCl2 of easily accessible 5-nitroisoxazoles substituted with an electron-withdrawing group (EWG) has been studied. Whereas the reaction in ethanol yielded 5-aminoisoxazoles, performing the reaction in tetrahydrofuran gave previously unknown 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles. Both reduction procedures were optimized to afford the corresponding products in good to excellent yields. Some mechanistic details concerning the inclusion of the tetrahydrofuranyl moiety into the reaction product are discussed
• Straightforward chemoselective 4-nitration of 5-aminoisoxazoles
  作者：Kirill S. Sadovnikov、Dmitry A. Vasilenko、Kseniya N. Sedenkova、Victor B. Rybakov、Yuri K. Grishin、Vera A. Alferova、Tamara S. Kuznetsova、Elena B. Averina

  DOI：10.1016/j.mencom.2020.07.027

  日期：2020.7

  5-Aminoisoxazoles bearing 3-positioned electron-withdrawing group react chemoselectively with trifluoroacetyl nitrate (generated from ammonium nitrate and trifluoroacetic anhydride) to give the corresponding 4-nitro derivatives in yields up to 80%. The results were rationalized by computation studies. Several 5-amino-4-nitroisoxazole-3-carboxilic acid derivatives revealed moderate antibacterial activity

  带有3-位吸电子基团的5-氨基异恶唑与三氟乙酰硝酸盐（由硝酸铵和三氟乙酸酐生成）发生化学选择性反应，得到相应的4-硝基衍生物，产率高达80％。通过计算研究使结果合理化。几种5-氨基-4-硝基异恶唑-3-羧酸衍生物显示出中等的抗菌活性。