hexahydro-2-methyl-5,10-ethano-1H-<1.2.4>triazolo<1.2-a><1.2>diazocine-1.3(2H)-dione | 54168-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: hexahydro-2-methyl-5,10-ethano-1H-<1.2.4>triazolo<1.2-a><1.2>diazocine-1.3(2H)-dione
• 英文别名: hexahydro-2-methyl-5,10-ethano-1H-[1.2.4]triazolo[1.2-a][1.2]diazocine-1.3(2H)-dione；4-Methyl-2,4,6-triazatricyclo[5.4.2.02,6]tridecane-3,5-dione；4-methyl-2,4,6-triazatricyclo[5.4.2.02,6]tridecane-3,5-dione
• CAS: 54168-19-3
• 化学式: C₁₁H₁₇N₃O₂
• 分子量: 223.275
• InChiKey: RLBUGNFENDGJKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环辛二烯 、 4-甲基-1,2,4-三吖啉-3,5-二酮 在 palladium on activated charcoal 氢气 作用下， 生成 hexahydro-2-methyl-5,10-ethano-1H-<1.2.4>triazolo<1.2-a><1.2>diazocine-1.3(2H)-dione
  参考文献：
  名称：

  Effects of CNN bond angle restriction in 2,3-diazabicyclo[2.1.1]hexane derivatives on nitrogen inversion barrier, ease of oxidation, and acidity

  摘要：

  Restriction of the CNN angle of triazolidinedione 3 by the presence of the diazabicyclo[2.1.1]hexyl system causes the nitrogens to be more pyramidal than tetrahedral (alpha(av) for crystalline 3 is 109.2-degrees) and produces a double nitrogen inversion barrier of 8.7 kcal/mol at-72-degrees-C in CD2Cl2. Although the pyramidality at N in tricyclic triazolidinedione derivatives experimentally lies near the prediction by PM3 semiemprical calculations, such calculations give barriers to double nitrogen inversion that are considerably too high. The effect of enlarging the size of the fused bicyclic system on ease of oxidation was determined: 3, E-degrees' + 1.77 V [VIP = 8.77 eV]; 5, 1.53 [8.68]; 6, 1.32 [8.60]; 7, 1.32 [8.15]; 8, 1.31 [7.90]. VIP values for azo compound 4 from PE spectroscopy are 9.3, 11.1, and 12.1 eV. The acidity of protonated bicyclic azo compounds varies 5.1 pK units between 4 (pK(a) -2.1) and 12 (pK(a) + 3.0).

  DOI：

  10.1021/jo00002a024

文献信息

• Effects of CNN bond angle restriction in 2,3-diazabicyclo[2.1.1]hexane derivatives on nitrogen inversion barrier, ease of oxidation, and acidity
  作者：Stephen F. Nelsen、Peter A. Petillo、Hao Chang、Timothy B. Frigo、Dennis A. Dougherty、Menahem Kaftory

  DOI：10.1021/jo00002a024

  日期：1991.1

  Restriction of the CNN angle of triazolidinedione 3 by the presence of the diazabicyclo[2.1.1]hexyl system causes the nitrogens to be more pyramidal than tetrahedral (alpha(av) for crystalline 3 is 109.2-degrees) and produces a double nitrogen inversion barrier of 8.7 kcal/mol at-72-degrees-C in CD2Cl2. Although the pyramidality at N in tricyclic triazolidinedione derivatives experimentally lies near the prediction by PM3 semiemprical calculations, such calculations give barriers to double nitrogen inversion that are considerably too high. The effect of enlarging the size of the fused bicyclic system on ease of oxidation was determined: 3, E-degrees' + 1.77 V [VIP = 8.77 eV]; 5, 1.53 [8.68]; 6, 1.32 [8.60]; 7, 1.32 [8.15]; 8, 1.31 [7.90]. VIP values for azo compound 4 from PE spectroscopy are 9.3, 11.1, and 12.1 eV. The acidity of protonated bicyclic azo compounds varies 5.1 pK units between 4 (pK(a) -2.1) and 12 (pK(a) + 3.0).