3-(1,5-Dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)propanoic acid | 372518-47-3

• 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-(1,5-Dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)propanoic acid
• CAS: 372518-47-3
• 化学式: C₁₁H₁₅N₃O₆
• 分子量: 285.257
• InChiKey: JJXVJDMAUBWCHU-UHFFFAOYSA-N

物化性质

• 沸点：
  505.4±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(1,5-Dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)propanoic acid 在 氯 作用下， 以 四氯化碳 为溶剂， 以97%的产率得到3-(2-carboxyethyl)-1,5-dinitro-6-chloro-3-azoniatricyclo[3.3.1.0^3,7]nonane chloride
  参考文献：
  名称：

  Chlorination features of 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes

  摘要：

  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.

  DOI：

  10.1134/s1070428006080203
• 作为产物：
  描述：

  1,3-二硝基苯 、 聚合甲醛 、 β-丙氨酸 在 钾硼氢 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以53%的产率得到3-(1,5-Dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)propanoic acid
  参考文献：
  名称：

  3-氮杂双环[3.3.1]壬烷衍生物：IV。3-氮杂双环[3.3.1]壬烷片段的氨基酸合成

  摘要：

  A series of 1.5-dinitro-3-azabicyclo[3.3.1]non-6-enes was prepared by reduction of 1-R-2,4- and 1-R-3,5-dinitrobenzenes with potassium borohydride followed by Mannich reaction with formaldehyde and amino acids. The molecular structure of (6-bromo-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic acid was studied by X-ray diffraction analysis. The mechanism of decomposition under electron impact was determined for (7-methoxy-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic acid.

  DOI：

  10.1023/a:1012402523702

文献信息

• 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.
• ——
  作者：I.V. Shakhkel'、E.G. Nikiforova、Yu.D. Grudtsyn、Yu.M. Atroshchenko、O.Ya. Borbulevich、Yu.A. Efremov、S.S. Gitis、D.N. Moiseev、E.N. Alifanova、P.V. Chudakov、A.Yu. Kovalevskii

  DOI：10.1023/a:1012402523702

  日期：——

  A series of 1.5-dinitro-3-azabicyclo[3.3.1]non-6-enes was prepared by reduction of 1-R-2,4- and 1-R-3,5-dinitrobenzenes with potassium borohydride followed by Mannich reaction with formaldehyde and amino acids. The molecular structure of (6-bromo-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic acid was studied by X-ray diffraction analysis. The mechanism of decomposition under electron impact was determined for (7-methoxy-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic acid.
• 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.