2,2-(pentamethylene)-propane-1,3-diol dinitrate | 110539-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 2,2-(pentamethylene)-propane-1,3-diol dinitrate
• 英文别名: Nitric acid [1-(nitrooxymethyl)cyclohexyl]methyl ester；[1-(nitrooxymethyl)cyclohexyl]methyl nitrate
• CAS: 110539-11-2
• 化学式: C₈H₁₄N₂O₆
• 分子量: 234.209
• InChiKey: WMEUOLLLSXLLSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [1-(羟基甲基)环己基]甲醇 在 三甲基氯硅烷 、 五氧化二氮 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,2-(pentamethylene)-propane-1,3-diol dinitrate
  参考文献：
  名称：

  清洁硝化作用：使用五氧化二氮（N 2 O 5）通过亚硝基甲硅烷基化反应进行的硝胺和硝酸酯的新型合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(97)00093-8

文献信息

• The reaction of 3-substituted oxetanes with nitric acid in dichloromethane
  作者：Kevin A. Hylands、Roy B. Moodie

  DOI：10.1039/a607257g

  日期：——

  The reactions of 3-phenyloxetane 1, 3-(4-nitrophenyl)oxetane 5 and 3,3-pentamethyleneoxetane 7 with nitric acid in dichloromethane or trichloromethane under anhydrous conditions have been investigated. Quantitative conversion to 2-substituted propane-1,3-diol dinitrates occurs. Compound 1 reacts initially by a mixture of ortho- and para-aromatic nitration and oxetane ring-opening. Aromatic nitrations of 1 and 1,4-dichlorobenzene, the former reacting through its majority hydrogen-bonded complexed form, are approximately sixth order in nitric acid and proceed at a comparable rate. The oxetane ring-opening reactions are approximately second order in nitric acid except in the case of 3-(2-nitrophenyl)oxetane 3, where there is evidence of intramolecular catalysis by the nitro group.

  在无水条件下，3-苯基环氧乙烷1、3-(4-硝基苯基)环氧乙烷5和3,3-戊二烯基环氧乙烷7与硝酸在二氯甲烷或三氯甲烷中的反应已被研究。它们均完全转化为2-取代丙烷-1,3-二硝酸酯。化合物1的反应首先是通过苯环邻位和对位的硝化和环氧环的开环。1和1,4-二氯苯的苯环硝化反应，前者通过其主要氢键络合形式进行，硝酸浓度对反应速率的依赖约为六级，且反应速率相近。环氧环开环反应对硝酸的依赖约为二级，除了3-(2-硝基苯基)环氧乙烷3，其硝基基团显示出分子内催化作用的证据。
• Nitration by oxides of nitrogen, part 1: preparation of nitrate esters by reaction of strained-ring oxygen heterocycles with dinitrogen pentoxide
  作者：P. Golding、R W Millar、N C Paul、D H Richards (deceased)

  DOI：10.1016/0040-4039(88)85272-9

  日期：——

  Epoxides and oxetanes react with dinitrogen pentoxide to give the corresponding dinitrates in high to near quantitative yields. The scope and limitations of the method are briefly discussed.

  环氧化物和氧杂环丁烷与五氧化二氮反应生成高或接近定量收率的相应二硝酸盐。简要讨论了该方法的范围和局限性。
• Preparation of di- and polynitrates by ring-opening nitration of oxetanes by dinitrogen pentoxide (N2O5)
  作者：Peter Golding、Ross W Millar、Norman C Paul、David H Richards

  DOI：10.1016/s0040-4020(01)87979-5

  日期：1993.8

  esters (I) by ring-opening nitration. The yields ranged from 73 to 88% for di-/trinitrates derived from oxetanes unsubstituted in the 2-position, to only 15 to 21% for oxetanes bearing such substituents. Although selective ring cleavage of oxetanes bearing non-hydroxylic substituents (epoxy (oxiranyl), spiro-oxetane and alkene) was not, in general, possible, selective nitration of hydroxyalkyloxetanes

  十个带有各种取代基的氧杂环丁烷在氯化烃溶剂中与N 2 O 5反应，生成1,3-二硬脂酸酯（I）通过开环硝化作用。衍生自在2-位未被取代的氧杂环丁烷的二/三硝酸盐的产率为73-88％，而带有此类取代基的氧杂环丁烷的产率为15-21％。虽然带有非羟基取代基（环氧（环氧乙烷基），螺-氧杂环丁烷和烯烃）的氧杂环丁烷的选择性环裂解是不可能的，但通常来说，在用于产生可用作前体的硝基-甲基氧杂环丁烷的条件下，可以实现羟烷基氧杂环丁烷的选择性硝化。高能聚醚。与代表性环氧化物的半定量反应性比较表明，氧杂环丁烷对N 2 O 5的反应性较低，这是由于其较低的环应变所预期的。
• Sila-Substitution of Alkyl Nitrates: Synthesis, Structural Characterization, and Sensitivity Studies of Highly Explosive (Nitratomethyl)-, Bis(nitratomethyl)-, and Tris(nitratomethyl)silanes and Their Corresponding Carbon Analogues
  作者：Camilla Evangelisti、Thomas M. Klapötke、Burkhard Krumm、Anian Nieder、Raphael J. F. Berger、Stuart A. Hayes、Norbert W. Mitzel、Dennis Troegel、Reinhold Tacke

  DOI：10.1021/ic902387y

  日期：2010.6.7

  A series of analogous nitratomethyl compounds of carbon and silicon of the formula types Me3EICH2ONO2 (1a/1b), Me2EI(CH2ONO2)(2) (2a/2b), MeEI(CH2ONO2)(3) (3a/3b), (CH2)(4)EI(CH2ONO2)(2) (4a/4b), and (CH2)(5)EI(CH2ONO2)(2) (5a/5b) were synthesized [El = C (a), Si (b); (CH2)(4)EI = (sila)cyclopentane-1,1-diy1; (CH2)(5)EI = (sila)cyclohexane-1,1-diy1]. All compounds were characterized by using NMR, IR, and Raman spectroscopy and mass spectrometry. In addition, the crystal structures of Me2C(CH2ONO2)(2) (2a), (CH2)(4)C(CH2ONO2)(2) (4a), Me2Si(CH2ONO2)(2) (2b), and (CH2)(5)Si(CH2ONO2)(2) (5b) were determined by single-crystal X-ray diffraction. The gas-phase structures of the C/Si analogues la and lb were determined by electron diffraction and compared with the results of quantum chemical calculations at different levels of theory. The thermal stabilities of the C/Si pairs la/lb-5a/5b were investigated by using DSC. In addition, their friction and impact sensitivities were measured with standard BAM methods. The extreme sensitivities of the silicon compounds lb 5b compared to those of the corresponding carbon analogues 1a 5a were discussed in terms of the structures of the C/Si analogues and possible geminal Si center dot center dot center dot O interactions.
• A process for the production of high energy material
  申请人：Secretary of State for Defence in Her Britannic Majesty's Gov. of the United Kingdom of Great Britain and Northern Ireland

  公开号：EP0223440B1

  公开（公告）日：1991-03-06