1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane
• 英文别名: 11-Methyl-3,4,8,9-tetraoxa-1,6-diazabicyclo[4.4.2]dodecane；11-methyl-3,4,8,9-tetraoxa-1,6-diazabicyclo[4.4.2]dodecane
• 化学式: C₇H₁₄N₂O₄
• 分子量: 190.199
• InChiKey: BWXQRZRJXMFKIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 1,2-丙二胺 在 双氧水 、 溶剂黄146 作用下， 以72%的产率得到1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane
  参考文献：
  名称：

  Cage peroxides having planar bridgehead nitrogen atoms

  摘要：

  Three new cage peroxides, 1,6-diaza-3,4,8,9-tetraoxabicyclo[4.4.2]dodecane (3a),1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane (3b), and 1,6-diaza-3,4,8,9-tetraoxatricyclo[4.4.2.4(11,12)]hexadecane (4), have been prepared by reaction of 1,2-diaminoethane, 1,2-diaminopropane, and trans-1,2-diaminocyclohexane, respectively, with formaldehyde and hydrogen peroxide in aqueous acidic solution. Their structures have been established by X-ray diffraction, and show the bridgehead nitrogen atoms to be predominantly sp(2) hybridized. The structures accord with H-1 and C-13 NMR spectra. Variable temperature NMR studies show that the diperoxide 3a begins to undergo rapid inversion (on the NMR time scale) at about 303 K; up to 370 K the diperoxides 3b and 4 show no conformational change.

  DOI：

  10.1139/cjc-77-5-6-1057

文献信息

• Cage peroxides having planar bridgehead nitrogen atoms
  作者：John T. Edward、Francis L. Chubb、Denis F.R. Gilson、Rosemary C. Hynes、Françoise Sauriol、Alain Wiesenthal

  DOI：10.1139/cjc-77-5-6-1057

  日期：——

  Three new cage peroxides, 1,6-diaza-3,4,8,9-tetraoxabicyclo[4.4.2]dodecane (3a),1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane (3b), and 1,6-diaza-3,4,8,9-tetraoxatricyclo[4.4.2.4(11,12)]hexadecane (4), have been prepared by reaction of 1,2-diaminoethane, 1,2-diaminopropane, and trans-1,2-diaminocyclohexane, respectively, with formaldehyde and hydrogen peroxide in aqueous acidic solution. Their structures have been established by X-ray diffraction, and show the bridgehead nitrogen atoms to be predominantly sp(2) hybridized. The structures accord with H-1 and C-13 NMR spectra. Variable temperature NMR studies show that the diperoxide 3a begins to undergo rapid inversion (on the NMR time scale) at about 303 K; up to 370 K the diperoxides 3b and 4 show no conformational change.