1-硝基吡咯烷 | 3760-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-硝基吡咯烷
• 英文名称: N-nitropyrrolidine
• 英文别名: 1-nitropyrrolidine
• CAS: 3760-55-2
• 化学式: C₄H₈N₂O₂
• 分子量: 116.12
• InChiKey: WHBIEWRKFNSHNY-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  260.4±7.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 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：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-硝基吡咯烷 以 丙酮 为溶剂， 生成 N-亚硝基吡咯烷 、 alkaline earth salt of/the/ methylsulfuric acid
  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：

  1-甲酰吡咯烷 在 硝酸铵 、 三氟乙酸酐 作用下， 以 硝基甲烷 为溶剂， 反应 0.75h， 以78%的产率得到1-硝基吡咯烷
  参考文献：
  名称：

  A Convenient Method ForN-Nitration Using Ammonium Nitrate/Trifluoroacetic Anhydride

  摘要：

  发现硝酸铵和三氟乙酸酐的混合物是一种方便的N-硝化试剂，用于合成硝胺、硝酰胺和硝酰亚胺。其产率与传统但更不方便或安全的硝化试剂相当。

  DOI：

  10.1055/s-1988-27696

文献信息

• Electrophilic tetraalkylammonium nitrate nitration. I. Convenient new anhydrous nitronium triflate synthesis and in-situ heterocyclic N-nitration
  作者：Christopher M. Adams、Clay M. Sharts、Scott A. Shackelford

  DOI：10.1016/s0040-4039(00)61671-4

  日期：1993.10

  Reaction of tetra-n-butylammonium nitrate and triflic anhydride, CF3SO2OSO2CF3 (Tf2O), in dichloromethane (CH2Cl2) solvent at 0 degrees C, produces anhydrous nitronium nitrate, NO2OSO2CF3 (NO2OTf). Subsequent introduction of various heterocycles and their N-acetylated analogs yield N-nitrated products in 20–76% yield with an overall one-pot procedure.

  硝酸四正丁基铵与三氟甲磺酸CF 3 SO 2 OSO 2 CF 3（Tf 2 O）在二氯甲烷（CH 2 Cl 2）溶剂中于0摄氏度下反应，生成无水硝酸硝氮，NO 2 OSO 2 CF 3（NO 2 OTf）。随后引入各种杂环及其N-乙酰化类似物，通过整体一锅法可得到20-76％的N-硝化产物。
• Formation of <i>N</i>-Nitrosamines and <i>N</i>-Nitramines by the Reaction of Secondary Amines with Peroxynitrite and Other Reactive Nitrogen Species:  Comparison with Nitrotyrosine Formation
  作者：Mitsuharu Masuda、Howard F. Mower、Brigitte Pignatelli、Irena Celan、Marlin D. Friesen、Hoyoku Nishino、Hiroshi Ohshima

  DOI：10.1021/tx990120o

  日期：2000.4.1

  mechanism, involving one-electron oxidation by peroxynitrite of secondary amines to form amino radicals (R(2)N(*)), which react with nitric oxide ((*)NO) or nitrogen dioxide ((*)NO(2)) to yield nitroso and nitro secondary amines, respectively. Reaction of morpholine with NO(*) and superoxide anion (O(2)(*)(-)), which were concomitantly produced from spermine NONOate and by the xanthine oxidase systems, respectively

  活性氮物质包括氮氧化物（N（2）O（3）和N（2）O（4）），过氧亚硝酸盐（ONOO（-））和硝酰氯（NO（2）Cl）被暗示为引起炎症和癌症的原因。我们研究了仲胺与过氧亚硝酸盐的反应，发现同时形成了N-亚硝胺和N-硝胺。在碱性pH下，过氧亚硝酸盐比在中性pH下更容易被亚硝酸盐亚硝化，而在pH 8.5下，过氧亚硝酸盐的硝化作用是最佳的。该反应中亚硝基吗啉的收率是碱性pH下亚硝基吗啉的3倍，而在pH <7.5下形成的亚硝基吗啉是亚硝基吗啉的2倍。对于吗啉-过亚硝酸盐反应，低浓度的碳酸氢盐可增强硝化作用，但过量的碳酸氢盐可抑制硝化作用。亚硝酸盐被过量的碳酸氢盐抑制。在此基础上，我们提出了一种自由基机理，涉及一种通过仲胺的过氧亚硝酸盐单电子氧化形成氨基（R（2）N（*））的基团，该基团与一氧化氮（（*）NO）或二氧化氮反应（（*）NO（2））分别产生亚硝基和硝基仲胺。吗啉与NO（*）和超氧阴离子（
• 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。
• Process for Synthesizing Nitramine Compounds
  申请人：Johnson Adam

  公开号：US20090286994A1

  公开（公告）日：2009-11-19

  There is disclosed a process for synthesizing nitrosamine compounds. Specifically, there is disclosed a process for synthesizing N-nitropyrrolidine.

  本发明公开了一种合成亚硝胺化合物的方法。具体地，本发明公开了一种合成N-亚硝基吡咯烷的方法。
• Alkaline Nitration. I. The Nitration of Amines with Cyanohydrin Nitrates¹
  作者：William D. Emmons、Jeremiah P. Freeman

  DOI：10.1021/ja01621a059

  日期：1955.8