Saekee Amporn, Kuhakarn Chutima, Chakarawet Khetpakorn, Hongthong Sakchai
Department of Chemistry and Center of Excellence for Innovation in Chemistry, (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
Acta Crystallogr E Crystallogr Commun. 2025 Feb 14;81(Pt 3):219-223. doi: 10.1107/S2056989025001070. eCollection 2025 Mar 1.
5,10-Dihy-droxy-9-meth-oxy-2,2-dimethyl-12-(2-methyl-but-3-en-2-yl)-2,6-pyrano[3,2-]xanthen-6-one, CHO (), is a prenylated xanthone that was synthesized from 5,9,10-trihy-droxy-2,2-dimethyl-12-(2-methyl-but-3-en-2-yl)-2,6-pyrano[3,2-]xanthen-6-one or macluraxanthone (), a known compound isolated from Pierre. The present study describes the synthesis of compound by methyl-ation reaction of , and its crystallographic characterization. Compound 2 features a planar xanthone core and a bent pyrano ring adopting a half-boat conformation. An intermolecular O-H⋯O hydrogen bond between the hydroxyl hydrogen donor and the ketone acceptor organizes the molecules into a one-dimensional network along the -axis direction. Perpendicular to this network, π-π stacking interactions form the three-dimensional supramolecular architecture. These two key intermolecular interactions are distinctly revealed in the Hirshfeld surface analysis.
5,10 - 二羟基 - 9 - 甲氧基 - 2,2 - 二甲基 - 12 - (2 - 甲基 - 丁 - 3 - 烯 - 2 - 基) - 2,6 - 吡喃并[3,2 - ]呫吨 - 6 - 酮，CHO（），是一种异戊烯基呫吨酮，它由5,9,10 - 三羟基 - 2,2 - 二甲基 - 12 - (2 - 甲基 - 丁 - 3 - 烯 - 2 - 基) - 2,6 - 吡喃并[3,2 - ]呫吨 - 6 - 酮或桑色素呫吨酮（）合成，桑色素呫吨酮是从皮埃尔中分离出的一种已知化合物。本研究描述了通过对的甲基化反应合成化合物及其晶体学表征。化合物2具有一个平面的呫吨酮核心和一个呈半船式构象的弯曲吡喃环。羟基氢供体和酮受体之间的分子间O - H⋯O氢键将分子沿轴方向组织成一维网络。垂直于该网络，π - π堆积相互作用形成三维超分子结构。这两种关键的分子间相互作用在 Hirshfeld 表面分析中得到了清晰的揭示。
