Dipartimento di Chimica, Università degli Studi di Milano, Milan 20133, Italy.
J Nat Prod. 2020 Oct 23;83(10):2894-2901. doi: 10.1021/acs.jnatprod.0c00436. Epub 2020 Sep 29.
The chemical reactivity of cannabidiol is based on its ability to undergo intramolecular cyclization driven by the addition of a phenolic group to one of its two double bonds. The main products of this cyclization are Δ-THC (-Δ-9-tetrahydrocannabinol) and Δ-THC (-Δ-8-tetrahydrocannabinol). These two cannabinoids are isomers, and the first one is a frequently investigated psychoactive compound and pharmaceutical agent. The isomers Δ--THC (-Δ-8--tetrahydrocannabinol) and Δ--THC (-Δ-4,8--tetrahydrocannabinol) have been identified as additional products of intramolecular cyclization. The use of Lewis and protic acids in different solvents has been studied to investigate the possible modulation of the reactivity of CBD (cannabidiol). The complete NMR spectroscopic characterizations of the four isomers are reported. High-performance liquid chromatography analysis and H NMR spectra of the reaction mixture were used to assess the percentage ratio of the compounds formed.
大麻二酚的化学反应性基于其在酚基团加成到其两个双键之一时发生分子内环化的能力。该环化的主要产物是 Δ-THC（-Δ-9-四氢大麻酚）和 Δ-THC（-Δ-8-四氢大麻酚）。这两种大麻素是同分异构体，前者是一种经常被研究的精神活性化合物和药物制剂。已经确定同分异构体 Δ--THC（-Δ-8--四氢大麻酚）和 Δ--THC（-Δ-4,8--四氢大麻酚）是分子内环化的其他产物。已经研究了路易斯酸和质子酸在不同溶剂中的使用，以研究 CBD（大麻二酚）的反应性的可能调节。报告了四个同分异构体的完整 NMR 光谱特征。使用高效液相色谱分析和反应混合物的 H NMR 光谱评估了形成的化合物的百分比比例。
