1,3-oxazinane is an ideal framework for advanced energetic materials because of its compact skeleton and the presence of several modifiable sites. However, investigations on characterization and performance of 1,3-oxazinane energetic compounds are extremely limited. Two heterocyclic 1,3-oxazinane molecules were synthesized under different Mannich condensation processes and further reacted to form nitro- and azide-substituted energetic compounds 3,5,5-trinitro-1,3-oxazinane (TNTON) and 5-azido-3,5-dinitro-1,3-oxazinane (ADTON), in good yields. Interestingly, the two energetic molecules showed distinct physical properties. ADTON shows an impressive glass transition temperature (Tg) as low as -46 °C with high density, which is highly suitable for rate-accelerating materials. TNTON exhibits good thermal stabilities (melting point of 89 °C and a decomposition point of 231 °C) and highly insensitive behavior (38 J, 360 N). The theoretical detonation pressure of TNTON is ca. 63 % higher than that of TNT, indicating broad application prospects in melt-cast explosives.

中文翻译：

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基于1,3-氧杂嗪烷的有前途的高能材料的合成，表征和性能。

1,3-恶嗪烷因其紧凑的骨架和多个可修饰位点而成为高级含能材料的理想框架。然而，关于1，3-恶嗪烷高能化合物的表征和性能的研究非常有限。在不同的曼尼希缩合过程中合成了两个杂环1,3-恶嗪烷分子，并进一步反应形成硝基和叠氮取代的高能化合物3,5,5-三硝基-1,3-恶嗪烷（TNTON）和5-叠氮基3 ，5-二硝基-1,3-恶嗪烷（ADTON），收率高。有趣的是，这两种高能分子显示出不同的物理性质。ADTON显示出低至-46°C且高密度的令人印象深刻的玻璃化转变温度（Tg），非常适用于速率加速材料。TNTON具有良好的热稳定性（熔点为89°C，分解点为231°C）和高度不敏感的行为（38 J，360 N）。TNTON的理论爆轰压力为。比TNT高63％，表明在熔铸炸药中具有广阔的应用前景。