3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene | 24543-30-4

• 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: 3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene
• CAS: 24543-30-4
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: UJTVOFSDBXXRSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 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：

  3-methyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以84%的产率得到3-methyl-3-azabicyclo[3.3.1]non-6-ene-1,5-diamine trihydrochloride
  参考文献：
  名称：

  Selective reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes

  摘要：

  Reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes gives either saturated 1,5-diamino-3-azabicyclo[3.3.1]nonane or unsaturated 1,5-diamino-3-azabicyclo[3.3.1]non-6-enes, depending on the conditions and nature of substituent in the substrate.

  DOI：

  10.1134/s1070428011060078

文献信息

• Chlorination features of 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes
  作者：Yu. M. Atroshchenko、N. K. Melekhina、I. V. Shakhkel’dyan、I. E. Yakunina、A. N. Shchukin、E. V. Shuvalova、V. A. Subbotin

  DOI：10.1134/s1070428006080203

  日期：2006.8

  The electrophilic chlorine addition to 3-substituted 1,5-dinitro-3-azabicyclo[3.3.1]-non-6-enes in the tetrachloromethane is accompanied at an intramolecular 3,7-cyclization giving 6-chloro-3-R-1,5-dinitro-3-azoniatricyclo[3.3.1.03,7]nonane chlorides. The reaction of the tricyclic quaternary ammonium salts with sodium methoxide leads to the formation of dealkylated and dehydrohalogenated products, 3-substituted 8-chloro-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes, bicyclic products with a halogen atom in an allyl position with respect to the double bond.
• 3-Azabicyclo[3.3.1]nonane Derivatives: IX. Synthesis and Molecular Structure of 3-Azabicyclo[3.3.1]nonane-1,5-diamines in Solution and in Solid State
  作者：M. V. Kopyshev、I. V. Shakhkeldyan、L. M. Kozlova、E. F. Litvin、V. Z. Sharf、N. A. Troitskii、Yu. M. Atroshchenko、E. N. Alifanova、M. B. Nikishina、I. N. Vorontsov、D. V. Gurylev

  DOI：10.1023/b:rujo.0000034950.28394.e0

  日期：2004.2

  During catalytic reduction with hydrogen on nickel of a series of 3-substituted 1,5-dinitro-3-azabicyclo-[3.3. 1]non-6-enes alongside nitro groups reduction occurred also hydrogenation of the double bond. New diamines of the 3)-azabicyclo[3.3. I]nonane series were synthesized, and their structure was established by means of IR, H-1 and C-13 NMR spectroscopy and X-ray diffraction study.
• 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.
• Selective reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes
  作者：I. E. Yakunina、A. N. Shchukin、M. V. Kopyshev、I. V. Shakhkel’dyan、A. N. Shumskii、A. A. Yakovenko、K. A. Lysenko、Yu. M. Atroshchenko

  DOI：10.1134/s1070428011060078

  日期：2011.6

  Reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes gives either saturated 1,5-diamino-3-azabicyclo[3.3.1]nonane or unsaturated 1,5-diamino-3-azabicyclo[3.3.1]non-6-enes, depending on the conditions and nature of substituent in the substrate.