氯代-1,4-二羟基蒽醌类中间体的合成、表征与性质

以多种氯代苯酐和对苯二酚为起始原料、无水三氯化铝为催化剂，通过Ffiedel—Crafts反应合成了多种氯代-1，4-二羟基蒽醌，利用UV-Vis、IR和^1HNMR等对制得的化合物进行了结构表征．结果表明：苯环上的氯原子对氯代苯酐的酰化活性具有明显的致钝作用，氯原子数量越多致钝作用越强，α-氯原子的致钝作用明显高于β-氯原子，表明氯原子的共轭效应是影响氯代苯酐酰化活性的主导因素；氯代-1，4-二羟基蒽醌分子中，氯原子的共轭效应提高了羰基的电子云密度，使分子内的氢键缔合增强，氯原子的诱导效应降低了异环的电子云密度．

Synthesis, Characterization and Properties of Chloro- 1,4- Dihydroxyanthraquinones

A series of chloro-1,4-dihydroxyanthraquinones were synthesized by the reaction of hydroquinone with chlorophenylanhydrides and anhydrous aluminium chloride as catalyst according to Friedel-Crafts reaction. All the compounds were characterized by UV-Vis, IR and ^1HNMR. The results show that the chlorine of phenyl has inactivation effect on acylating ability of chlorophenylanhydride. The inactivation effect increases with the increase of the number of chlorines and the a-chlorine performs stronger effect than r-chlorine, which show that the conjugation of chlorine is the key to affecting the acylating ability of chlorophenylanhydrides. In molecule of chloro-1,4- dihydroxyanthraquinones, the conjugation of chlorine increases the density of electron cloud of carbonyl groups and their H-bonding combination for the chlorohydroxyanthraquinones. The induction effect of chlorine decreases the density of electron cloud of another aromatic ring.