Cubane, Bicyclo[1.1.1]pentane and Bicyclo[2.2.2]octane: Impact and Thermal Sensitiveness of Carboxyl-, Hydroxymethyl- and Iodo-substituents

被引:20
作者
Dallaston, Madeleine A. [1 ]
Houston, Sevan D. [1 ]
Williams, Craig M. [1 ]
机构
[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia
基金
澳大利亚研究理事会;
关键词
bicyclo[1; 1; pentane; bicyclo[2; 2; 2]octane; cubane; sensitiveness; Yoshida; STRAIN ENERGIES; ACID; DERIVATIVES; AZIDOCUBANES; FLUORIDES; CHEMISTRY; REAGENTS; DESIGN;
D O I
10.1002/chem.202001658
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
With the burgeoning interest in cage motifs for bioactive molecule discovery, and the recent disclosure of 1,4-cubane-dicarboxylic acid impact sensitivity, more research into the safety profiles of cage scaffolds is required. Therefore, the impact sensitivity and thermal decomposition behavior of judiciously selected starting materials and synthetic intermediates of cubane, bicyclo[1.1.1]pentane (BCP), and bicyclo[2.2.2]octane (BCO) were evaluated via hammer test and sealed cell differential scanning calorimetry, respectively. Iodo-substituted systems were found to be more impact sensitive, whereas hydroxymethyl substitution led to more rapid thermodecomposition. Cubane was more likely to be impact sensitive with these substituents, followed by BCP, whereas all BCOs were unresponsive. The majority of derivatives were placed substantially above Yoshida thresholds-a computational indicator of sensitivity.
引用
收藏
页码:11966 / 11970
页数:5
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