9,9-dimethyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione | 38375-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 9,9-dimethyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione
• 英文别名: dimethylpropanediurea；9,9-dimethyl-2,4,6,8-tetraaza-bicyclo[3.3.1]nonane-3,7-dione；2,4,6,8-Tetraazabicyclo[3.3.1]nonane-3,7-dione, 9,9-dimethyl-；9,9-dimethyl-2,4,6,8-tetrazabicyclo[3.3.1]nonane-3,7-dione
• CAS: 38375-84-7
• 化学式: C₇H₁₂N₄O₂
• 分子量: 184.198
• InChiKey: GGVYMQYTAMNBDY-UHFFFAOYSA-N

物化性质

• 沸点：
  600.4±55.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,9-dimethyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione 在 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 19.0h， 生成 4,7,15,18-Tetramethoxy-23,23-dimethyl-1,10,12,21-tetrazahexacyclo[19.3.1.03,8.010,24.012,22.014,19]pentacosa-3,5,7,14,16,18-hexaene-11,25-dione
  参考文献：
  名称：

  Molecular Clips Based on Propanediurea. Exceptionally High Binding Affinities for Resorcinol Guests

  摘要：

  A series of new receptor molecules derived from 2,4,6,8-tetraazabicyclo [3.3.1]nonane-3,7-dione (propanediurea) is described. These molecules possess a cavity which is defined by two nearly parallel aromatic side walls positioned on top of a bis-urea framework. The resulting "U-shaped" clip molecules are ideal hosts for the complexation of flat aromatic guest molecules. The affinity of these new propanediurea based molecular clips for dihydroxybenzene derivatives is exceptionally high, with association constants up to K-a = 2 400 000 L mol(-1). Comparison of the binding mechanism of a variety of clip and half clip hosts, in conjunction with NMR, IR, and X-ray studies, has enabled the reason for this high binding to be elucidated. It is shown that subtle sub-angstrom changes in the geometry of the clip molecules have a great impact on their binding properties.

  DOI：

  10.1021/jo001317k
• 作为产物：
  描述：

  二甲基丙二醛 、 尿素 在 硫酸 、 溶剂黄146 作用下， 反应 12.0h， 以2.8 g的产率得到9,9-dimethyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione
  参考文献：
  名称：

  对银具有高亲和力的最小的葫芦素类似物。

  摘要：

  在CaCl2作为模板的情况下，由丙二脲-甲醛缩合首次制备了新的宿主Me8TD [4]，它是迄今为止报道的最小的葫芦科类似物。用等温滴定热法测量了Me8TD [4]与一系列阳离子相互作用的热力学量（log K，ΔH和ΔS值），表明Me8TD [4]选择性地以高结合常数K结合到Ag +上。 1.3×106 M-1。

  DOI：

  10.1039/c7cc01729d

文献信息

• Synthesis, X-ray structure and binding properties of molecular clips based on dimethylpropanediurea
  作者：Rob J. Jansen、Alan E. Rowan、Hans W. Scheeren、Roeland J. M. Nolte、Rob J. Jansen、René de Gelder

  DOI：10.1039/a706012b

  日期：——

  New concave host molecules show strong noncovalent binding of hydroxybenzene derivatives by an induced fit mechanism (Ka up to 3.4 × 106 dm3 mol–1).

  新的凹面宿主分子通过诱导拟合机制（Ka 高达 3.4 × 106 dm3 mol-1）显示出与羟苯衍生物的强力非共价结合。
• A cucurbit[5]uril analogue from dimethylpropanediurea–formaldehyde condensation
  作者：Xiaoqing Jiang、Xuyang Yao、Xinghua Huang、Qiaochun Wang、He Tian

  DOI：10.1039/c4cc09900a

  日期：——

  A new cucurbit[5]uril-like macrocycle has been synthesized and shows good solubility in water and organic solvents.

  一种新的类西瓜环[5]葡萄糖苷样大环已经合成，能够在水和有机溶剂中良好地溶解。
• Pressocucurbit[5]uril
  作者：Lukas Ustrnul、Petr Kulhanek、Tomas Lizal、Vladimir Sindelar

  DOI：10.1021/acs.orglett.5b00123

  日期：2015.2.20

  A novel macrocycle, decamethylpressocucurbit[5]uril (Me(10)prCB-[5]), was synthesized by acid-catalyzed condensation of propanediurea and paraformaldehyde. This macrocycle binds methane with higher affinity than cucurbit[5]uril and its permethylated derivative
• CYBOPOBA L. I.; ERESKO V. A.; EPISHINA L. V.; LEBEDEV O. V.; XMELNITSKIJ +, IZV. AN CCCP. CEP. XIM., 1979, HO 6, 1306-1313
  作者：CYBOPOBA L. I.、 ERESKO V. A.、 EPISHINA L. V.、 LEBEDEV O. V.、 XMELNITSKIJ +

  DOI：——

  日期：——
• The smallest cucurbituril analogue with high affinity for Ag⁺
  作者：Yufan Wu、Lixi Xu、Yenan Shen、Yang Wang、Lei Zou、Qiaochun Wang、Xiaoqing Jiang、Jiansen Liu、He Tian

  DOI：10.1039/c7cc01729d

  日期：——

  new host, Me8TD[4], was prepared for the first time from propanediurea-formaldehyde condensation in the presence of CaCl2 as the template and it is the smallest cucurbituril analogue reported so far. Measurements of the thermodynamic quantities (log K, ΔH, and ΔS values) of the interactions of Me8TD[4] with a series of cations by isothermal titration calorimetry indicated that Me8TD[4] binds selectively

  在CaCl2作为模板的情况下，由丙二脲-甲醛缩合首次制备了新的宿主Me8TD [4]，它是迄今为止报道的最小的葫芦科类似物。用等温滴定热法测量了Me8TD [4]与一系列阳离子相互作用的热力学量（log K，ΔH和ΔS值），表明Me8TD [4]选择性地以高结合常数K结合到Ag +上。 1.3×106 M-1。