1,3,3,5,5-pentanitropiperidine | 71706-07-5

• 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: 1,3,3,5,5-pentanitropiperidine
• 英文别名: 1,3,3,5,5-pentanitro-piperidine；Piperidine, 1,3,3,5,5-pentanitro-
• CAS: 71706-07-5
• 化学式: C₅H₆N₆O₁₀
• 分子量: 310.137
• InChiKey: IBPRZWSDOFZNQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  232
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,3,5,5-pentanitropiperidine 以 四氢呋喃 为溶剂， 80.0 ℃ 、66.66 Pa 条件下， 生成 二氧化碳
  参考文献：
  名称：

  Evidence of an Elimination Mechanism in Thermal Decomposition of Hexahydro-1,3,5-trinitro-1,3,5-triazine and Related Compounds under High Pressure in Solution

  摘要：

  The thermal decomposition of a number of six-membered cyclic nitramines and nitrosamines was studied under pressures up to 1.1 GPa in dilute solution (THF). The studied nitramines and nitrosamines include hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) hexahydro-5-methyl-1,3,5-trinitropyrimidine, hexahydro-1,3,5,5-tetranitropyrimidine, 1,3,3,5,5-pentanitrbpiperidine, and hexahydro-1,3,5-trinitroso-1,3,5-triazine (TRDX). In all cases negative activation volumes have been found, indicating that thermolysis is not a homolytic process. On the basis of negative activation volumes, detection of aromatic products, low decomposition temperature (low E-a), and order of thermal stability, we propose that these cyclic nitramines and nitrosamines are thermally decomposed through the elimination of HNO2 or HNO under-high pressure. By summarizing our current and previous work, we find that the decomposition pathway of nitrosamines and nitrosamines is dependent not only on the reaction conditions but also on structural features.

  DOI：

  10.1021/jo970775z
• 作为产物：
  描述：

  2-(3,3,5,5-四硝基哌啶-1-基)乙酸 在 硝酸 、 三氟乙酸酐 作用下， 反应 17.0h， 以98%的产率得到1,3,3,5,5-pentanitropiperidine
  参考文献：
  名称：

  (3,3,5,5-Tetranitropiperidin-1-yl)acetic Acid: Precursor for 1,3,3,5,5-Pentanitropiperidine

  摘要：

  (3,3,5,5-四硝基哌啶-1-基)乙酸是 1,3,3,5,5-五硝基哌啶的一种新颖而经济的前体。将 2,2-二硝基丙烷-1,3-二醇与甘氨酸在 65-70 ËC的水中处理 5 小时后，得到（3,3,5,5-四硝基哌啶-1-基）乙酸，分离收率为 52%。后者在 100%硝酸和三氟乙酸酐的混合物中硝化 12 小时后，得到 1,3,3,5,5-戊硝基哌啶，基本定量。(3,3,5,5-Tetranitropiperidin-1-yl)acetic acid 和 1,3,3,5,5-pentanitropiperidine 通过红外光谱、核磁共振（¹H、¹³C 和 ¹5N）光谱、差示扫描量热法和元素分析进行了全面表征。

  DOI：

  10.1055/s-0031-1289682

文献信息

• Nitrolysis of dialkyl tert-butylamines
  作者：Dorothy A. Cichra、Horst G. Adolph

  DOI：10.1021/jo00133a047

  日期：1982.6
• CICHRA, D. A.;ADOLPH, H. G., J. ORG. CHEM., 1982, 47, N 12, 2474-2476
  作者：CICHRA, D. A.、ADOLPH, H. G.

  DOI：——

  日期：——
• Evidence of an Elimination Mechanism in Thermal Decomposition of Hexahydro-1,3,5-trinitro-1,3,5-triazine and Related Compounds under High Pressure in Solution
  作者：Jiang Wang、Kay R. Brower、Darren L. Naud

  DOI：10.1021/jo970775z

  日期：1997.12.1

  The thermal decomposition of a number of six-membered cyclic nitramines and nitrosamines was studied under pressures up to 1.1 GPa in dilute solution (THF). The studied nitramines and nitrosamines include hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) hexahydro-5-methyl-1,3,5-trinitropyrimidine, hexahydro-1,3,5,5-tetranitropyrimidine, 1,3,3,5,5-pentanitrbpiperidine, and hexahydro-1,3,5-trinitroso-1,3,5-triazine (TRDX). In all cases negative activation volumes have been found, indicating that thermolysis is not a homolytic process. On the basis of negative activation volumes, detection of aromatic products, low decomposition temperature (low E-a), and order of thermal stability, we propose that these cyclic nitramines and nitrosamines are thermally decomposed through the elimination of HNO2 or HNO under-high pressure. By summarizing our current and previous work, we find that the decomposition pathway of nitrosamines and nitrosamines is dependent not only on the reaction conditions but also on structural features.
• (3,3,5,5-Tetranitropiperidin-1-yl)acetic Acid: Precursor for 1,3,3,5,5-Pentanitropiperidine
  作者：Jean’ne Shreeve、Rajendra Singh

  DOI：10.1055/s-0031-1289682

  日期：2012.3

  (3,3,5,5-Tetranitropiperidin-1-yl)acetic acid is a novel and economical precursor for 1,3,3,5,5-pentanitropiperidine. Treatment of 2,2-dinitropropane-1,3-diol with glycine in water at 65-70 ˚C for five hours gave (3,3,5,5-tetranitropiperidin-1-yl)acetic acid in 52% isolated yield. Nitration of the latter in a mixture of 100% nitric acid and trifluoroacetic anhydride for 12 hours gave 1,3,3,5,5-pentanitropiperidine in essentially quantitative yield. (3,3,5,5-Tetranitropiperidin-1-yl)acetic acid and 1,3,3,5,5-pentanitropiperidine were fully characterized by means of IR and NMR (¹H, ¹³C, and ¹5N) spectroscopy, differential scanning calorimetry, and elemental analysis.

  (3,3,5,5-四硝基哌啶-1-基)乙酸是 1,3,3,5,5-五硝基哌啶的一种新颖而经济的前体。将 2,2-二硝基丙烷-1,3-二醇与甘氨酸在 65-70 ËC的水中处理 5 小时后，得到（3,3,5,5-四硝基哌啶-1-基）乙酸，分离收率为 52%。后者在 100%硝酸和三氟乙酸酐的混合物中硝化 12 小时后，得到 1,3,3,5,5-戊硝基哌啶，基本定量。(3,3,5,5-Tetranitropiperidin-1-yl)acetic acid 和 1,3,3,5,5-pentanitropiperidine 通过红外光谱、核磁共振（¹H、¹³C 和 ¹5N）光谱、差示扫描量热法和元素分析进行了全面表征。