2-(dinitromethylene)-1,3-diazacyclohexane | 137143-83-0

• 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: 2-(dinitromethylene)-1,3-diazacyclohexane
• 英文别名: 2-(Dinitromethylene)hexahydropyrimidine；2-(dinitromethylidene)-1,3-diazinane
• CAS: 137143-83-0
• 化学式: C₅H₈N₄O₄
• 分子量: 188.143
• InChiKey: CXRUHFKXRYIVMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(dinitromethylene)-1,3-diazacyclohexane 在 硝酸 、 乙酸酐 作用下， 反应 5.0h， 以83.6%的产率得到3-Nitro-2-(trinitromethyl)-1,3-diazacyclohex-1-ene
  参考文献：
  名称：

  1-硝基-2-三硝基甲基取代的咪唑：新型高性能含能材料†

  摘要：

  设计并合成了一系列新的1-硝基-2-三硝基甲基取代的咪唑。所有化合物均通过多核NMR和IR光谱，元素分析（EA）和差示扫描量热法（DSC）进行表征。化合物的X-射线结构测定11-15，17和19表明，其密度范围从1.59克厘米-3到1.86克厘米-3，给见解其结构特点表示广泛氢键相互作用的存在。这些新材料大多数都显示出正形成热（HOF = 145.7–344.8 kJ mol -1），可接受的氧平衡和灵敏度值（IS = 10.4–32.5 J，FS = 85–240 N）。根据计算出的HOF和密度，使用EXPLO5 V6.01计算了爆炸速度（D）和压力（P），表明某些三硝基甲基材料（D = 8688–8764 ms -1，P = 34.4–35.1 GPa）具有可比性到1,3,5-三硝基过氢-1,3,5-三嗪（RDX，D = 8795 ms -1，P = 34.9 GPa）。在新的衍生物中，17（ρ

  DOI：

  10.1039/c6ta08831g
• 作为产物：
  描述：

  1,1-diiodo-2,2-dinitroethylene 、 1,3-丙二胺 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 2-(dinitromethylene)-1,3-diazacyclohexane
  参考文献：
  名称：

  1,1-二氨基-2,2-二硝基乙烯总是两性离子。

  摘要：

  四碘乙烯（7）的硝化反应生成1,1-二碘-2,2-二硝基乙烯（8）。后者与烷基胺9或烷基二胺11反应，分别得到相应的无环1，1-二氨基-2，2-二硝基乙烯10或它们的环状类似物12。根据液态和固态（13）C和（15）N NMR数据，x射线分析和从头算计算，我们建议标题化合物始终为两性离子，C（A）-C（N ）键不是真正的双键。

  DOI：

  10.1002/mrc.3861

文献信息

• Nitration of 1,1-diamino-2,2-dinitroethylenes
  作者：Kurt Baum、Nguyen Nghi Van、Richard Gilardi、Judith L. Flippen-Anderson、Clifford George

  DOI：10.1021/jo00037a015

  日期：1992.5

  The nitration of 1,1-diamino-2,2-dinitroethylenes, obtained by the reaction of amines with 1,1-diiododinitroethylene, was studied. Reaction of 2-(dinitromethylene)-1,3-diazacyclopentane (la) with nitric acid and trifluoroacetic anhydride in methylene chloride gave 3-nitro-2-(trinitromethyl)-1,3-diazacyclopent-1-ene (3a) in high yield. Analogous products 3b-3d were obtained from 2-(dinitromethylene)-1,3-diazacyclohexane (1b), 2-(dinitromethylene)-1,3-diazacycloheptane (1c), and 3,9-bis(dinitromethylene)-2,4,8,10-tetraazaspiro[5.5]undecane (1d). Nitration of 1a with nitric acid in sulfuric acid gave the corresponding nitrosamine 2a. Reductive denitrations of the trinitromethyl compounds 3a, 3b, and 3c with potassium iodide gave salts of the corresponding dinitromethyl compounds 4a, 4b, and 4c. Bromination and chlorination of 4a afforded 2-(bromodinitromethyl)-3-nitro-1,3-diazacyclopentent-1-ene (5) and 2-(chlorodinitromethyl)-3-nitro-1,3-diazacyclopent-1-ene (6), respectively. Acidification of the salts 4a, 4b, and 4c gave 2-(dinitromethylene)-1-nitro-1,3-diazacyclopentane (7a), 2-(dinitromethylene)-1-nitro-1,3-diazacyclohexane (7b), and 2-(dinitromethylene)-1-nitro-1,3-diazacycloheptane (7c), respectively. The nitration of 7a gave 3a. Nitrations of the diamino mononitro olefins, 2-(nitromethylene)-1, 3-diazacyclopentane (8a) and 2-(nitromethylene)-1,3-diazacyclohexane (8b), gave 3a and 3b. The structures of 3a, 3d, 7a, 7b, and 7c were obtained by X-ray crystallography. Olefin twist angles for 7a-7c, as high as 74.5-degrees, are rationalized on the bases of ring geometry and hydrogen bonding.
• Synthesis and reactions of 1,1-diiododinitroethylene
  作者：Kurt Baum、Sean S. Bigelow、Nguyen Nghi Van、Thomas G. Archibald、Richard Gilardi、Judith L. Flippen-Anderson、Clifford George

  DOI：10.1021/jo00027a042

  日期：1992.1

  The nitration of tetraiodoethylene gave 1,1-diiododinitroethylene (1). X-ray crystallography showed that one of the two nitro groups is perpendicular to the ethylene plane. Simple amines (dimethylamine, propylamine, aniline) reacted with 1 to give 1,1-diamino-2,2-dinitroethylene derivatives; diamines (o-phenylenediamine, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane) gave the corresponding cyclic products, and a tetramine [(tetrakis(aminomethyl)methane] gave the analogous spiro derivative. Ammonia gave only ammonium cyanodinitromethide, whereas phenol gave 1,1-dinitro-2,2,2-triphenoxyethane. The reaction of 1 with potassium nitrite gave the dipotassium salt of tetranitroethane. X-ray crystallography of the 1,1-diamino-2,2-dinitroethylenes showed twisted olefins, some with twist angles greater than any previously reported for twisted ethylenes, with concomitant bond-distance distortions.
• 1-Nitro-2-trinitromethyl substituted imidazoles: a new family of high performance energetic materials
  作者：Yuangang Xu、Cheng Shen、Qiuhan Lin、Pengcheng Wang、Chao Jiang、Ming Lu

  DOI：10.1039/c6ta08831g

  日期：——

  A new series of 1-nitro-2-trinitromethyl substituted imidazoles were designed and synthesized. All the compounds were characterized by multinuclear NMR and IR spectroscopies, elemental analysis (EA), and differential scanning calorimetry (DSC). X-ray structure determination of compounds 11–15, 17 and 19 showed that their densities range from 1.59 g cm−3 to 1.86 g cm−3 and gave insights into their structural

  设计并合成了一系列新的1-硝基-2-三硝基甲基取代的咪唑。所有化合物均通过多核NMR和IR光谱，元素分析（EA）和差示扫描量热法（DSC）进行表征。化合物的X-射线结构测定11-15，17和19表明，其密度范围从1.59克厘米-3到1.86克厘米-3，给见解其结构特点表示广泛氢键相互作用的存在。这些新材料大多数都显示出正形成热（HOF = 145.7–344.8 kJ mol -1），可接受的氧平衡和灵敏度值（IS = 10.4–32.5 J，FS = 85–240 N）。根据计算出的HOF和密度，使用EXPLO5 V6.01计算了爆炸速度（D）和压力（P），表明某些三硝基甲基材料（D = 8688–8764 ms -1，P = 34.4–35.1 GPa）具有可比性到1,3,5-三硝基过氢-1,3,5-三嗪（RDX，D = 8795 ms -1，P = 34.9 GPa）。在新的衍生物中，17（ρ
• 1,1-Diamino-2,2-dinitroethylenes are always zwitterions
  作者：Pessia Gilinsky-Sharon、Hugo E. Gottlieb、David E. Rajsfus、Keren Keinan-Adamsky、Vered Marks、Pinchas Aped、Aryeh A. Frimer

  DOI：10.1002/mrc.3861

  日期：2012.10

  or alkyldiamines 11 to give the corresponding acyclic 1,1-diamino-2,2-dinitroethylenes 10 or their cyclic analogs 12, respectively. On the basis of liquid and solid-state (13)C and (15)N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the C(A)-C(N) bond is not a true double bond.

  四碘乙烯（7）的硝化反应生成1,1-二碘-2,2-二硝基乙烯（8）。后者与烷基胺9或烷基二胺11反应，分别得到相应的无环1，1-二氨基-2，2-二硝基乙烯10或它们的环状类似物12。根据液态和固态（13）C和（15）N NMR数据，x射线分析和从头算计算，我们建议标题化合物始终为两性离子，C（A）-C（N ）键不是真正的双键。