4,6,10-trihydroxy-1,4,6,10-tetraazaadamantane | 1186489-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4,6,10-trihydroxy-1,4,6,10-tetraazaadamantane
• 英文别名: 1,4,6,10-tetraazatricyclo[3.3.1.1(3,7)]decane-4,6,10-triol；4,6,10-trihydroxy-1,4,6,10-tetrazatricyclo[3.3.1.13,7]decane
• CAS: 1186489-49-5
• 化学式: C₆H₁₂N₄O₃
• 分子量: 188.186
• InChiKey: QAPJJBNCGHJPNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6,10-trihydroxy-1,4,6,10-tetraazaadamantane 在 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到hexamethylenetetramine
  参考文献：
  名称：

  Urotropine Isomer (1,4,6,10-Tetraazaadamantane): Synthesis, Structure, and Chemistry

  摘要：

  The first synthesis of 1,4,6,10-tetraazaadamantane, the C-3v-symmetrical structural isomer of urotropine (1,3,5,7-tetraazaadamantane), and a series of its derivatives is reported. X-ray and quantum-chemical studies revealed remarkable distinctions in structures of urotropine and "isourotropine" cations, probably arising from different types of hyperconjugation between lone electron pairs of nitrogen atoms and sigma(C-N)* orbitals in these heterocage systems. Since substitution at bridge and bridgehead nitrogen atoms can be easily introduced, 1,4,6,10-tetraazaadamantane may be considered as a new rigid multivalent (3 + 1) scaffold for the design of functional molecules and materials.

  DOI：

  10.1021/jo5007703
• 作为产物：
  描述：

  {bis[2-(hydroxyimino)ethyl]amino}ethanal oxime 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以89%的产率得到4,6,10-trihydroxy-1,4,6,10-tetraazaadamantane
  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