4,11-Dinitro-14H-<1,2,5>oxadiazolo<3,4-e><1,2,5>oxadiazolo<3',4':4,5>benzotriazolo<2,1-a>benzotriazol-6-ium inner salt 1,8-dioxide | 2180101-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 4,11-Dinitro-14H-<1,2,5>oxadiazolo<3,4-e><1,2,5>oxadiazolo<3',4':4,5>benzotriazolo<2,1-a>benzotriazol-6-ium inner salt 1,8-dioxide
• 英文别名: 4,15-Dinitro-8,19-dioxido-7,18-dioxa-6,11,12,17-tetraza-1,8,19-triazonia-22-azanidahexacyclo[10.10.0.02,10.05,9.013,21.016,20]docosa-1,3,5,8,10,13(21),14,16,19-nonaene
• CAS: 2180101-63-5
• 化学式: C₁₂H₂N₁₀O₈
• 分子量: 414.21
• InChiKey: UYLYDYKDPVKNAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  217
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,11-Dinitro-14H-<1,2,5>oxadiazolo<3,4-e><1,2,5>oxadiazolo<3',4':4,5>benzotriazolo<2,1-a>benzotriazol-6-ium inner salt 1,8-dioxide 在 三氟甲磺酸 、 硝酸 作用下， 以 硝基甲烷 为溶剂， 反应 2.17h， 生成 4,5,11,12-tetraoxo-14H-[1,2,5]oxadiazolo[3,4-e][1,2,5]oxadiazolo[3',4':4,5]benzotriazolo[2,1-a]benzotriazol-6-ium inner salt 1,8-dioxide
  参考文献：
  名称：

  Reactions of Benzotriazolo[2,1-a]benzotriazole Derivatives. 2. An Unusual Hydrolysis−Oxidation Reaction

  摘要：

  DOI：

  10.1021/jo951889i
• 作为产物：
  描述：

  1,3,7,9-四硝基-6H-苯并三唑并[2,1-a]苯并三唑-5-鎓内盐 在 sodium azide 、 硝酸 作用下， 以 二甲基亚砜 为溶剂， 反应 4.17h， 生成 4,11-Dinitro-14H-<1,2,5>oxadiazolo<3,4-e><1,2,5>oxadiazolo<3',4':4,5>benzotriazolo<2,1-a>benzotriazol-6-ium inner salt 1,8-dioxide
  参考文献：
  名称：

  Reactions of Benzotriazolo[2,1-a]benzotriazole Derivatives. 1. Synthesis of New Insensitive High-Density Energetic Compounds

  摘要：

  The sequential preference of electrophilic attack on the dibenzotetraazapentalene ring system 6 has unequivocally been shown to be in the order of position 2(8) > 4(10) much greater than 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to be substrate dependent. Substitution occurred at the 3(9)-position of 9 followed by elimination of hydrogen chloride to give 10 while direct substitution of azide for the 8(10)-nitro group of 2 was found to yield 13. The reactivity of the dibenzotetraazapentalene derivatives toward electrophiles and nucleophiles was exploited for the synthesis of the new heterocyclic system 14H-[1,2,5]oxadiazolo[3,4-e][1,2,5]oxadiazolo[3',4':4,5]benzotriazolo[2,1-alpha]benzotriazol-6-ium inner salt 1,8-dioxide (11). From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2.

  DOI：

  10.1021/jo00124a024

文献信息

• Reactions of Benzotriazolo[2,1-a]benzotriazole Derivatives. 1. Synthesis of New Insensitive High-Density Energetic Compounds
  作者：Ganesan Subramanian、Joseph H. Boyer、Dan Buzatu、Edwin D. Stevens、Mark L. Trudell

  DOI：10.1021/jo00124a024

  日期：1995.9

  The sequential preference of electrophilic attack on the dibenzotetraazapentalene ring system 6 has unequivocally been shown to be in the order of position 2(8) > 4(10) much greater than 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to be substrate dependent. Substitution occurred at the 3(9)-position of 9 followed by elimination of hydrogen chloride to give 10 while direct substitution of azide for the 8(10)-nitro group of 2 was found to yield 13. The reactivity of the dibenzotetraazapentalene derivatives toward electrophiles and nucleophiles was exploited for the synthesis of the new heterocyclic system 14H-[1,2,5]oxadiazolo[3,4-e][1,2,5]oxadiazolo[3',4':4,5]benzotriazolo[2,1-alpha]benzotriazol-6-ium inner salt 1,8-dioxide (11). From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2.
• Reactions of Benzotriazolo[2,1-<i>a</i>]benzotriazole Derivatives. 2. An Unusual Hydrolysis−Oxidation Reaction
  作者：Ganesan Subramanian、Joseph H. Boyer、Mark L. Trudell、William M. Koppes、Michael E. Sitzmann, and、Lori A. Nock、Richard Gilardi、Thomas P. Russell

  DOI：10.1021/jo951889i

  日期：1996.1.1