{bis[2-(hydroxyimino)ethyl]amino}ethanal oxime | 1186489-41-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: {bis[2-(hydroxyimino)ethyl]amino}ethanal oxime
• CAS: 1186489-41-7
• 化学式: C₆H₁₂N₄O₃
• 分子量: 188.186
• InChiKey: IAQWVOYFKALVPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.4±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101.01
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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

文献信息

• Synthesis of B,O,N-Doped Adamantanes and Diamantanes by Condensation of Oximes with Boronic Acids
  作者：Ivan S. Golovanov、Alexey Yu. Sukhorukov、Yulia V. Nelyubina、Yulia A. Khomutova、Sema L. Ioffe、Vladimir A. Tartakovsky

  DOI：10.1021/acs.joc.5b00892

  日期：2015.7.2

  Condensation of Altos with boronic acids RB(OH)(2) or B(OH)(3) affords remarkably stable 2,4,10-trioxa-1,5,7-triaza-3-boroadamantanes via an unprecedented multicomponent process. The mechanism involves the reversible generation: of unstable oxime cyclotrimers, which are readily intercepted by borcinic acids.
• Urotropine Isomer (1,4,6,10-Tetraazaadamantane): Synthesis, Structure, and Chemistry
  作者：Artem N. Semakin、Alexey Yu. Sukhorukov、Yulia V. Nelyubina、Yulia A. Khomutova、Sema L. Ioffe、Vladimir A. Tartakovsky

  DOI：10.1021/jo5007703

  日期：2014.7.3

  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.