几种仲醇的选择性氧化研究  

The chemoselective oxidation of vicinal polyols

作　　者：刘敏[1] 刘娟[1] 李本浩 李夏冰[1] 李宝林[1] 

机构地区：[1]药用资源与天然药物化学教育部重点实验室,陕西师范大学化学化工学院,陕西西安710119

出　　处：《陕西师范大学学报（自然科学版）》2016年第3期75-78,共4页Journal of Shaanxi Normal University：Natural Science Edition

基　　金：国家自然科学基金(21272144)

摘　　要：为了将几种邻位醇中的仲羟基选择性催化氧化成相应的酮羰基,首先以2,9-二甲基-1,10-菲啰啉(neocuproine)、三氟甲磺酸(HOTf)和醋酸钯为原料反应生成钯的配合物[(neocuproine)Pd(OAc)]2(OTf)2;并以此配合物为催化剂,对苯醌或氧气为氧化剂,乙腈与水的混合物(体积比为9∶1)为溶剂,实现了1,2-O-异丙叉基-α-D-呋喃葡萄糖、1-苯基-1,2-乙二醇和1,2-癸二醇中仲羟基的选择性氧化,获得了预期的结果。尤其是对1-苯基-1,2-乙二醇的选择性氧化产率高达93.0%。This article presents a method for the selectively oxidation of the secondary hydroxyl group into the corresponding keto-carbonyl group.The complex [（neocuproine）Pd（OAc）]2（OTf）2synthesized from neocuproine（2,9-dimethyl-1,10-phenanthroline）, HOTf and Pd（OAc）2,was used as a catalyst to the selective oxidation of several vicinal polyols with pbenzoquinone or O2 as oxidant by using the mixture of acetonitrile and water（9∶1）as a solvent.This catalytic system was applied to the oxidation of several vicinal polyols including 1,2-Oisopropylidene-α-D-glucofuranose, 1-phenylethane-1,2-diol and 1,2-decanediol to afford correspondingα-hydroxy ketones in good yields.Especially for the selective oxidation of 1-phenylethane-1,2-diol,the chemical yield was up to 93.0%.

关 键 词：邻位醇 PD催化剂 选择性氧化 

分 类 号：O622.3[理学—有机化学]