ethyl 3-amino-2-(hydroxyimino)propanoate | 1186489-47-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 3-amino-2-(hydroxyimino)propanoate
• 英文别名: Ethyl 3-amino-2-hydroxyiminopropanoate
• CAS: 1186489-47-3
• 化学式: C₅H₁₀N₂O₃
• mdl: MFCD19215635
• 分子量: 146.146
• InChiKey: RJFVTGGNLRBXPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-2-(hydroxyimino)propanoate 、 N,N-bis(trimethylsilyloxy)-1-propen-2-amine 在 甲醇 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 以47%的产率得到ethyl (2Z)-3-{bis[(2E)-2-(hydroxyimino)propyl]amino}-2-(hydroxyimino)propanoate
  参考文献：
  名称：

  Unusual Intramolecular Cyclization of Tris(β-oximinoalkyl)amines. The First Synthesis of 1,4,6,10-Tetraazaadamantanes

  摘要：

  An unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines 1 into 4,6,10-trihydroxy-1,4,6,10-tetraazaadamantanes 2 was discovered. Compounds 2 are related to a previously unknown type of heteroadamantanes that contain the cage Isomeric to urotropin. A simple three-step synthesis of tetraazaadamantanes 2 and their N-substituted derivatives 3 and 4 from ammonia and aliphatic nitro compounds via the intermediacy of available tris-oximes 1 was developed.

  DOI：

  10.1021/ol9015157
• 作为产物：
  描述：

  ethyl 2-{bis[(trimethylsilyl)oxy]amino}acrylate 在 甲醇 、 氨 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到ethyl 3-{bis[3-(ethyloxy)-2-(hydroxyimino)-3-oxopropyl]amino}-2-(hydroxyimino)propanoate
  参考文献：
  名称：

  Unusual Intramolecular Cyclization of Tris(β-oximinoalkyl)amines. The First Synthesis of 1,4,6,10-Tetraazaadamantanes

  摘要：

  An unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines 1 into 4,6,10-trihydroxy-1,4,6,10-tetraazaadamantanes 2 was discovered. Compounds 2 are related to a previously unknown type of heteroadamantanes that contain the cage Isomeric to urotropin. A simple three-step synthesis of tetraazaadamantanes 2 and their N-substituted derivatives 3 and 4 from ammonia and aliphatic nitro compounds via the intermediacy of available tris-oximes 1 was developed.

  DOI：

  10.1021/ol9015157

文献信息

• Unusual Intramolecular Cyclization of Tris(β-oximinoalkyl)amines. The First Synthesis of 1,4,6,10-Tetraazaadamantanes
  作者：Artem N. Semakin、Alexey Yu. Sukhorukov、Alexey V. Lesiv、Sema L. Ioffe、Konstantin A. Lyssenko、Yulia V. Nelyubina、Vladimir A. Tartakovsky

  DOI：10.1021/ol9015157

  日期：2009.9.17

  An unusual intramolecular cyclization of tris(beta-oximinoalkyl)amines 1 into 4,6,10-trihydroxy-1,4,6,10-tetraazaadamantanes 2 was discovered. Compounds 2 are related to a previously unknown type of heteroadamantanes that contain the cage Isomeric to urotropin. A simple three-step synthesis of tetraazaadamantanes 2 and their N-substituted derivatives 3 and 4 from ammonia and aliphatic nitro compounds via the intermediacy of available tris-oximes 1 was developed.