6-bromo-3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene | 634169-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 6-bromo-3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene
• 英文别名: 3-Azabicyclo[3.3.1]non-6-ene, 6-bromo-3-methyl-1,5-dinitro-
• CAS: 634169-16-7
• 化学式: C₉H₁₂BrN₃O₄
• 分子量: 306.116
• InChiKey: XMQBZZLOUSYVLH-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 6-bromo-3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene 以 乙腈 为溶剂， 反应 48.0h， 以42%的产率得到6-bromo-3,3-dimethyl-1,5-dinitro-3-azoniabicyclo[3.3.1]non-6-ene iodide
  参考文献：
  名称：

  3-氮杂双环[3.3.1]壬烷衍生物：VIII。6（7）-R-3,3-二甲基-1,5-二硝基-3-氮杂双环[3.3.1]非6-烯碘化物的合成及性能

  摘要：

  N-Alkylation of 6(7)-R-1,5-dinitro-3-methyl-3-azabicyclo[3.3. I]non-6-enes with methyl iodide afforded a series of quaternary ammonium salts whose yield depended on the solvent polarity and character of substituents located in positions 6 or 7 of substrate. The presence of electron-withdrawing groups reduced the yield of the target products compared to unsubstituted compound, whereas the electron-donor substituents increased the yield. As shown by the X-ray diffraction study the congormation of the substances was not changed in the course of quaternization. The DTA-TG analysis revealed that in the first stage of thermolysis the 6(7)-R-3,3-dimethyl-1,5-dinitro-3-azoniabicyclo[3.3. I]non-6-ene iodides suffer dealkylation. Two fragmentation paths of compounds synthesized under electron impact were observed: elimination either of methyl iodide or aziridinium cation.

  DOI：

  10.1023/b:rujo.0000034949.33987.6b
• 作为产物：
  描述：

  1-溴-2,4-二硝基苯 、 聚合甲醛 、 甲胺 在 sodium tetrahydroborate 、 氢气 作用下， 以43%的产率得到6-bromo-3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene
  参考文献：
  名称：

  3-氮杂双环[3.3.1]壬烷衍生物：VIII。6（7）-R-3,3-二甲基-1,5-二硝基-3-氮杂双环[3.3.1]非6-烯碘化物的合成及性能

  摘要：

  N-Alkylation of 6(7)-R-1,5-dinitro-3-methyl-3-azabicyclo[3.3. I]non-6-enes with methyl iodide afforded a series of quaternary ammonium salts whose yield depended on the solvent polarity and character of substituents located in positions 6 or 7 of substrate. The presence of electron-withdrawing groups reduced the yield of the target products compared to unsubstituted compound, whereas the electron-donor substituents increased the yield. As shown by the X-ray diffraction study the congormation of the substances was not changed in the course of quaternization. The DTA-TG analysis revealed that in the first stage of thermolysis the 6(7)-R-3,3-dimethyl-1,5-dinitro-3-azoniabicyclo[3.3. I]non-6-ene iodides suffer dealkylation. Two fragmentation paths of compounds synthesized under electron impact were observed: elimination either of methyl iodide or aziridinium cation.

  DOI：

  10.1023/b:rujo.0000034949.33987.6b

文献信息

• 3-Azabicyclo[3.3.1]nonane Derivatives: VIII. Synthesis and Properties of 6(7)-R-3,3-Dimethyl-1,5- dinitro-3-azoniabicyclo[3.3.1]non-6-ene Iodides
  作者：I. V. Shakhkeldyan、N. K. Melekhina、Yu. M. Atroshenko、M. V. Kopyshev、O. Ya. Borbulevich、K. Yu. Suponitskii、M. Yu. Antipin、E. N. Alifanova、M. B. Nikisina、V. A. Subbotin

  DOI：10.1023/b:rujo.0000034949.33987.6b

  日期：2004.2

  N-Alkylation of 6(7)-R-1,5-dinitro-3-methyl-3-azabicyclo[3.3. I]non-6-enes with methyl iodide afforded a series of quaternary ammonium salts whose yield depended on the solvent polarity and character of substituents located in positions 6 or 7 of substrate. The presence of electron-withdrawing groups reduced the yield of the target products compared to unsubstituted compound, whereas the electron-donor substituents increased the yield. As shown by the X-ray diffraction study the congormation of the substances was not changed in the course of quaternization. The DTA-TG analysis revealed that in the first stage of thermolysis the 6(7)-R-3,3-dimethyl-1,5-dinitro-3-azoniabicyclo[3.3. I]non-6-ene iodides suffer dealkylation. Two fragmentation paths of compounds synthesized under electron impact were observed: elimination either of methyl iodide or aziridinium cation.