1,3-dinitroazetidine | 132395-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 1,3-dinitroazetidine
• 英文别名: Azetidine, 1,3-dinitro-
• CAS: 132395-40-5
• 化学式: C₃H₅N₃O₄
• 分子量: 147.09
• InChiKey: WYKTUOLGMMCABC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 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：
  94.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dinitroazetidine 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 、 sodium nitrite 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 以40%的产率得到1,3,3-trinitroazetidine
  参考文献：
  名称：

  A Novel Approach to the Synthesis of 1,3,3-trinitroazetidine

  摘要：

  DOI：

  10.1021/jo00120a049
• 作为产物：
  描述：

  3-nitro-1-nitrosoazetidine 在 硝酸 、 三氟乙酸酐 作用下， 反应 0.5h， 以90%的产率得到1,3-dinitroazetidine
  参考文献：
  名称：

  1-氮杂双环[1.1.0]丁烷生成和捕集的新方法。在合成1,3-二硝基氮杂环丁烷中的应用

  摘要：

  摘要 1-氮杂双环[1.1.0]丁烷 (1) 已通过两步一锅法制备，包括 (i) 烯丙胺的庚烷溶液与 N-氯琥珀酰亚胺在 0 °C 下反应，然后 (ii) ) 从碱性溶液中与庚烷-辛烷共蒸馏产物。通过使用冷的NaNO 2 水溶液从馏出物中提取由此获得的化合物1。随后用冷的浓盐酸水溶液处理水提取物，得到 N-亚硝基-3-硝基-氮杂环丁烷 (4)，产率为 5.5%。4 用 100% HNO3 氧化产生 N,3-二硝基氮杂环丁烷 (5, 90%)。该反应序列构成了重要的含能材料 1,3,3-三硝基氮杂环丁烷 (TNAZ) 的正式合成。

  DOI：

  10.1080/00397919808004953

文献信息

• New Method for the Generation and Trapping of 1-Azabicyclo[1.1.0]butane. Application to the Synthesis of 1,3-Dinitroazetidine
  作者：Romuald Bartnik、Dariusz Cal、Alan P. Marchand、Sulejman Alihodzic、Arokiasamy Devasagayaraj

  DOI：10.1080/00397919808004953

  日期：1998.11

  Abstract 1-Azabicyclo[1.1.0]butane (1) has been prepared via a two-step, one-pot procedure that involves (i) reaction of a heptane solution of allylamine with N-chlorosuccinimide at 0 °C followed by (ii) codistillation of the product from basic solution along with heptane-octane. Compound 1 thereby obtained was extracted from the distillate by using cold aqueous NaNO2. Subsequent treatment of the aqueous

  摘要 1-氮杂双环[1.1.0]丁烷 (1) 已通过两步一锅法制备，包括 (i) 烯丙胺的庚烷溶液与 N-氯琥珀酰亚胺在 0 °C 下反应，然后 (ii) ) 从碱性溶液中与庚烷-辛烷共蒸馏产物。通过使用冷的NaNO 2 水溶液从馏出物中提取由此获得的化合物1。随后用冷的浓盐酸水溶液处理水提取物，得到 N-亚硝基-3-硝基-氮杂环丁烷 (4)，产率为 5.5%。4 用 100% HNO3 氧化产生 N,3-二硝基氮杂环丁烷 (5, 90%)。该反应序列构成了重要的含能材料 1,3,3-三硝基氮杂环丁烷 (TNAZ) 的正式合成。
• A Novel Approach to the Synthesis of 1,3,3-trinitroazetidine
  作者：Alan P. Marchand、D. Rajagopal、Simon G. Bott、Thomas G. Archibald

  DOI：10.1021/jo00120a049

  日期：1995.7
• Thermal Decomposition Pathways of 1,3,3-Trinitroazetidine (TNAZ), Related 3,3-Dinitroazetidium Salts, and ¹⁵N,¹³C, and ²H Isotopomers
  作者：Jimmie Oxley、James Smith、Weiyi Zheng、Evan Rogers、Michael Coburn

  DOI：10.1021/jp9700950

  日期：1997.6.1

  The thermal decomposition of 1,3,3-trinitroazetidine (TNAZ) and related 3,3-dinitroazetidium (DNAZ(+)) salts was examined neat and in solution. TNAZ kinetics were found (160-250 degrees C) to be first-order and nearly identical neat and in benzene, with an activation energy of 46.6 kcal/mol (195 kJ/mol). The DNAZ(+) salts were less thermally stable than TNAZ, and neat did not decompose in a first-order fashion. However, in aqueous solution the DNAZ(+) salts did decompose following first-order kinetics; their rates were similar with minor differences apparently related to the strength of the anion as a conjugate base. Like simple nitramines such as dimethylnitramine, TNAZ tended to form N2O rather than N-2, but unlike other nitramines it formed about as much NO as N2O. TNAZ isotopomers labeled with C-13 and with N-15 were prepared and used to identify the origin of the decomposition gases and the identity of the condensed-phase products. Early in the decomposition of TNAZ, most of the NO came from the nitro group attached to the azetidium ring nitrogen. Most of the N2O was the result of the nitro groups interacting with each other, while the majority of the N-2 contained one nitrogen from the ring. Many condensed products have been identified, but five stand out because they are formed in the thermolysis of TNAZ and the three DNAZ(+) salts [NO3-, Cl-, N(NO2)(2)(-)]. These are 3,5-dinitropyridine (M, always a minor product), 1-formyl-3,3-dinitroazetidine (L), 1,3-dinitroazetidine (K), 1-nitroso-3,3-dinitroazetidine (E), and 1-nitroso-3-nitroazetidine (G); the identity of the first four has been confirmed by use of authentic samples. Of these five, the last four have been shown to interconvert with TNAZ and each other under the conditions of these experiments. This study confirms the presence of two competitive TNAZ decomposition pathways. Under the conditions of this study, N-NO2 homolysis is slightly favored, but products, such as K, resulting from C-NO2 scission, are also well represented.
• Improved Synthesis of an Energetic Material, 1,3,3-Trinitroazetidine Exploiting 1-Azabicyclo[1.1.0]butane
  作者：Yoshimitsu Nagao、Kazuhiiko Hayashi、Toshio Kumagai

  DOI：10.3987/com-99-8791

  日期：——