Construction of an All-Bridge Carbon-Oxidized 2-Azaadamantane Skeleton and Synthesis of Two Energetic Derivatives

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-24 DOI:10.1021/acs.orglett.5c00447

Qi Zhou, Huan Li, Long Zhu, Bing Li, Yunzhi Liu, Guixiang Wang, Yu Zhang, Jun Luo

引用次数: 0

Abstract

The construction of an all-bridge-oxygenated (hetero)adamantane skeleton is a long-standing challenge. Herein, an all-bridge carbon-oxidized 2-azaadamantane skeleton, 6,9,10-trimethoxy-2-azaadamantane-4,8-diol, was constructed via an eight-step synthetic route from 9-hydroxybicyclo[3.3.1]nonane-2,6-dione with an overall yield of 45%. The obtained skeleton was derived into two novel high-performance energetic compounds. Among them, 2,9,9,10,10-pentanitro-2-azaadamantane-4,6,8-triyl trinitrate is the first example that possesses eight explosophoric groups on the adamantane skeleton.

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全桥碳氧化2-氮杂金刚烷骨架的构建及两个含能衍生物的合成

构建全桥氧合（杂）金刚烷骨架是一个长期存在的挑战。本文以9-羟基双环壬烷-2,6-二酮为原料，经8步合成得到了全桥碳氧化的2-氮杂金刚烷骨架6,9,10-三甲氧基-2-氮杂金刚烷-4,8-二醇，总收率为45%。得到的骨架被衍生为两种新型的高性能能化合物。其中2,9,9,10,10-戊硝基-2-叠氮金刚烷-4,6,8-三硝基是金刚烷骨架上第一个具有8个爆炸基团的例子。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.