The emergence of new synthetic cathinones continues to be a matter of public health concern. In fact, already known products (drugs) are being rapidly replaced by new structurally related alternatives, whereby modifications in the basic cathinone structure are used by manufacturers to circumvent the legislation. On the other hand, some derivatives of synthetic cathinones represent important pharmaceuticals with antidepressant properties. In the search for pharmaceutically relevant analogs, the main goal of the present study was to design and characterize novel cyclic α-tetralone-based derivatives of synthetic cathinones. We synthesized a series of derivatives and verified their chemical structure. Subsequently, chiral separation has been accomplished by high-performance liquid chromatography (HPLC) equipped with a circular dichroism (CD) detector, which directly provided CD spectra of the enantiomers of the analyzed substances at 252 nm. Using density functional theory calculations, we have obtained stable conformers of selected enantiomers in solution and their relative abundances, which we used to simulate their spectra. The experimental and calculated data have been used to assign the absolute configuration of six as-yet unknown synthetic cathinones.

中文翻译：

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α-四氢萘酮衍生的环状合成卡西酮的合成和绝对构型

新合成卡西酮的出现仍然是公众健康关注的问题。事实上，已知的产品（药物）正在迅速被新的结构相关替代品所取代，制造商利用卡西酮基本结构的修改来规避立法。另一方面，一些合成卡西酮衍生物代表了具有抗抑郁特性的重要药物。在寻找药学相关类似物的过程中，本研究的主要目标是设计和表征新型环状 α-四氢萘酮基合成卡西酮衍生物。我们合成了一系列衍生物并验证了它们的化学结构。随后，通过配备圆二色性（CD）检测器的高效液相色谱（HPLC）完成手性分离，直接提供被分析物质的对映体在252 nm处的CD光谱。利用密度泛函理论计算，我们获得了溶液中选定对映体的稳定构象异构体及其相对丰度，我们用它来模拟它们的光谱。实验和计算数据已用于确定六种迄今未知的合成卡西酮的绝对构型。