CHINESE JOURNAL OF ENERGETIC MATERIALS
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三环[3.3.1.0³⁷]壬-2,6-二酮的构建及其四硝基衍生物的合成
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南京理工大学化学与化工学院

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基金项目:

国家自然科学基金(22075144)


Construction of Tricyclo[3.3.1.0³⁷]nonane-2,6-dione and Synthesis of Tetranitro-derivative
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Affiliation:

School of Chemical Engineering, Nanjing University of Science and Technology

Fund Project:

Grant support: National Natural Science Foundation of China (No. 22075144)

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    摘要:

    以双环[3.3.1]壬-2,6-二酮为原料,经溴化、环合、还原脱溴等步骤构建了一种新型笼状骨架三环[3.3.1.0³⁷]壬-2,6-二酮,再通过酮羰基的肟化和偕二硝化合成了一种新型笼状含能化合物2,2,6,6-四硝基三环[3.3.1.0³⁷]壬烷。利用核磁共振、红外、元素分析对目标化合物进行了结构表征,通过X-射线单晶衍射确定了晶体结构,采用热重分析(TG)和差示扫描量热法(DSC)联用研究了目标化合物的热稳定性,通过EXPLO5预测了其爆轰性能。结果表明:2,2,6,6-四硝基三环[3.3.1.0³⁷]壬烷的晶体密度为1.69 g·cm-3,属单斜晶系,P2/n空间群,起始分解温度为186 ℃,计算爆速为7319 m·s-1,爆压为21.57 GPa,显著高于金刚烷型同系物2,2,6,6-四硝基金刚烷。

    Abstract:

    A novel cage-like compound tricyclo[3.3.1.0³⁷]nonane-2,6-dione was synthesized from bicyclic[3.3.1]non-2,6-dione through bromination, cyclization and reductive debromination. Its energetic derivative 2,2,6,6-tetranitrotricyclo[3.3.1.0³⁷]nonane was prepared via oximation and gem-dinitration. The structure of target compound was characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), elemental analysis (EA), and single crystal X-ray diffraction (SC-XRD). The thermal stability was studied by differential scanning calorimetry (DSC) and thermogravimetric analysis (TG). The detonation performances were predicted by EXPLO5. Results show that 2,2,6,6-tetranitrotrycyclo[3.3.1.0³⁷]nonane crystallizes in the monoclinic crystal system, space group P2/n with a crystal density of 1.691 g∙cm-3. Its onset thermal decomposition temperature is 186 ℃. The theoretical detonation velocity and detonation pressure are 7319 m·s-1 and 21.57 GPa, respectively, which are much higher than that of its adamantane-based homologue 2,2,6,6-tetranitroadamantane.

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引用本文

祝龙,周琪,李欢,等.三环[3.3.1.0³⁷]壬-2,6-二酮的构建及其四硝基衍生物的合成[J].含能材料, 2026, 34(3):284-291. DOI:10.11943/CJEM2025240.
ZHU Long, ZHOU Qi, LI Huan, et al. Construction of Tricyclo[3.3.1.0³⁷]nonane-2,6-dione and Synthesis of Tetranitro-derivative[J]. Chinese Journal of Energetic Materials, 2026, 34(3):284-291. DOI:10.11943/CJEM2025240.

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历史
  • 收稿日期: 2025-10-29
  • 最后修改日期: 2026-02-07
  • 录用日期: 2026-01-26
  • 在线发布日期: 2026-02-05
  • 出版日期: 2026-03-25