1,3-dinitro-hexahydro-pyrimidine | 5754-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1,3-dinitro-hexahydro-pyrimidine
• 英文别名: 1,3-dinitro-1,3-diazacyclohexane；1,3-dinitro-1,3-diazinane
• CAS: 5754-89-2
• 化学式: C₄H₈N₄O₄
• 分子量: 176.132
• InChiKey: UMQHAPFYPBXHAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 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：
  98.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dinitro-hexahydro-pyrimidine 以 乙醇 为溶剂， 生成 二(N-亚硝基)-全氢化嘧啶
  参考文献：
  名称：

  Mechanisms of Nitramine Thermolysis

  摘要：

  The thermal decomposition of a number of nitramines was studied in dilute solution and in the melt, The nitramines included acyclic mononitramines [dimethylnitramine (DMN), diethylnitramine (DEN), dipropylnitramine (DPN), and diisopropylnitramine (DIPN)], cyclic mononitramines [N-nitropiperidine (NPIP) and N-nitropyrrolidine (NPyr)], cyclic dinitramines [N-dinitropiperazine (pDNP), 1,3-dinitro-1,3-diazacyclopentane (DNI), and 1,3-dinitro-1,3-diazacyclohexane (mDNP)], and 1,3,5-trinitro-1,3,5-triazocyclohexane (RDX), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), hexanitrohexaazaisowurtzitane (HNIW), and 1,3,3-trinitroazetidine (TNAZ). For the acyclic and cyclic mono- and dinitramines, the corresponding nitrosamines were the only or major condensed-phase product. Kinetics and activation parameters were determined for the thermolysis of dilute solutions (0.01-1.0 wt %) over the range 200-300 degrees C. The thermolyses were found to be first-order with the rate constants unaffected by the use of deuterated solvent. As the nitramines became more complex than dimethylnitramine (DMN), the rate of decomposition increased and the product distribution became more complex. As the length of the aliphatic chain increased (DMN < DEN < DPN), the rate of thermolysis increased, yet nitrosamine remained the only observed condensed-phase product. When a secondary carbon was attached to the N-nitramine (DIPN) rather than the primary (DPN), the rate of decomposition increased and a new condensed-phase product was observed. Among the cyclic nitramines, the rate of decomposition increased as the number of NNO2 groups increased (NPIP < pDNP; NPyr < DNI; mDMP < RDX). The position of the nitramine groups affected the decomposition: meta NNO2 groups (mDNP) decomposed faster than para (pDNP). Ring strain decreased stability: mDNP < DNI; HMX < RDX. In complex nitramines, the increase in decomposition rate, the appearance of new products, and the change in the relative importance of nitrosamine and of N-2 and N2O are attributed to new decomposition routes available to them. However, since complex nitramines (e.g. RDX) maintain first-order kinetics and since most have activation energies in the range of 40-50 kcal/mol, it is believed that the triggering mechanism remains N-NO2 homolysis. Intramolecular hydrogen transfer is also considered an important mode of nitramine decomposition.

  DOI：

  10.1021/j100079a019
• 作为产物：
  描述：

  二(N-亚硝基)-全氢化嘧啶 在 五氧化二氮 作用下， 以30%的产率得到1,3-dinitro-hexahydro-pyrimidine
  参考文献：
  名称：

  An alternate synthesis of cyclic 1,3-dinitramines

  摘要：

  DOI：

  10.1021/jo00200a026

文献信息

• Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N 2 O 5 )
  作者：Ross W. Millar、Simon P. Philbin

  DOI：10.1016/s0040-4020(97)00093-8

  日期：1997.3

  with conventional substrates (amines or alcohols). These nitrodesilylation reactions proceed cleanly and in good yield, and the scope of the reaction is illustrated by. 29 examples, some of which produce high energy compounds, notably plasticisers and an energetic polymer precursor. These reactions are therefore potentially clean nitrations for the manufacture of energetic compounds which will minimise

  在这种新型的硝化方法中，使用惰性溶剂中的五氧化二氮（N 2 O 5）作为硝化剂，从而无需使用强酸作为反应介质。N 2 O 5分别在甲硅烷基胺和甲硅烷基醚中裂解杂原子-硅键，得到所需的高能基团（分别为硝胺或硝酸酯），而不会释放常规底物（胺或醇）会发生的酸。这些氮代甲硅烷基化反应清洁且收率良好，反应范围如下所示。29个实例，其中一些可以生产高能化合物，尤其是增塑剂和高能聚合物前体。因此，这些反应是潜在的清洁硝化反应，可用于生产高能化合物，这将在将来最大程度地降低这种活性对环境的影响。
• Synthesis of polyazapolycyclic caged polynitramines
  作者：Arnold T. Nielsen、Andrew P. Chafin、Stephen L. Christian、Donald W. Moore、Melvin P. Nadler、Robin A. Nissan、David J. Vanderah、Richard D. Gilardi、Clifford F. George、Judith L. Flippen-Anderson

  DOI：10.1016/s0040-4020(98)83040-8

  日期：1998.9
• WILLER, R. L.;ATKINS, R. L., J. ORG. CHEM., 1984, 49, N 26, 5147-5150
  作者：WILLER, R. L.、ATKINS, R. L.

  DOI：——

  日期：——
• ——
  作者：WILLER R. L.、 ATKINS R. L.

  DOI：——

  日期：——
• Mechanisms of Nitramine Thermolysis
  作者：J. C. Oxley、A. B. Kooh、R. Szekeres、W. Zheng

  DOI：10.1021/j100079a019

  日期：1994.7

  The thermal decomposition of a number of nitramines was studied in dilute solution and in the melt, The nitramines included acyclic mononitramines [dimethylnitramine (DMN), diethylnitramine (DEN), dipropylnitramine (DPN), and diisopropylnitramine (DIPN)], cyclic mononitramines [N-nitropiperidine (NPIP) and N-nitropyrrolidine (NPyr)], cyclic dinitramines [N-dinitropiperazine (pDNP), 1,3-dinitro-1,3-diazacyclopentane (DNI), and 1,3-dinitro-1,3-diazacyclohexane (mDNP)], and 1,3,5-trinitro-1,3,5-triazocyclohexane (RDX), octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), hexanitrohexaazaisowurtzitane (HNIW), and 1,3,3-trinitroazetidine (TNAZ). For the acyclic and cyclic mono- and dinitramines, the corresponding nitrosamines were the only or major condensed-phase product. Kinetics and activation parameters were determined for the thermolysis of dilute solutions (0.01-1.0 wt %) over the range 200-300 degrees C. The thermolyses were found to be first-order with the rate constants unaffected by the use of deuterated solvent. As the nitramines became more complex than dimethylnitramine (DMN), the rate of decomposition increased and the product distribution became more complex. As the length of the aliphatic chain increased (DMN < DEN < DPN), the rate of thermolysis increased, yet nitrosamine remained the only observed condensed-phase product. When a secondary carbon was attached to the N-nitramine (DIPN) rather than the primary (DPN), the rate of decomposition increased and a new condensed-phase product was observed. Among the cyclic nitramines, the rate of decomposition increased as the number of NNO2 groups increased (NPIP < pDNP; NPyr < DNI; mDMP < RDX). The position of the nitramine groups affected the decomposition: meta NNO2 groups (mDNP) decomposed faster than para (pDNP). Ring strain decreased stability: mDNP < DNI; HMX < RDX. In complex nitramines, the increase in decomposition rate, the appearance of new products, and the change in the relative importance of nitrosamine and of N-2 and N2O are attributed to new decomposition routes available to them. However, since complex nitramines (e.g. RDX) maintain first-order kinetics and since most have activation energies in the range of 40-50 kcal/mol, it is believed that the triggering mechanism remains N-NO2 homolysis. Intramolecular hydrogen transfer is also considered an important mode of nitramine decomposition.