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通过对环氧化合物的亲核加成或直接还原可以得到各种各样的醇
环氧化合物和醇反应可以得到邻烷氧基醇、和硫醇反应可以得到邻烷硫基醇、和卤化氢反应生成邻卤醇、和水反应生成邻二醇、和叠氮酸反应生成邻叠氮基醇、和仲胺反应可以得到邻位叔胺基醇、和格氏试剂反应得到碳链增长两个的醇、用硼氢化钠、氢化 铝锂或氢气还原环氧化合物可以得到醇。
环氧化合物和叠氮酸反应生成邻叠氮基醇示例
To a solution of cis-2,3-epoxybutane (2 g, 27.74 mmol) in methanol/water (83 ML/8 ML), sodium azide (2.7 g, 41.61 mmol) and ammonium chloride (2.97 g, 55.48 mmol) were added.. The reaction mixture was stirred at reflux temperature for 16 hours.. Then cooled to room temperature and evaporated all solvent.. The residue was extracted with ethyl acetate.. The combined organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (2.6 g, 82percent). EI-MS m/z 88 (M+N2).
硼氢化钠还原环氧化合物得到醇示例
A mixture of 39.2 g (71.2 mmol) of (2S,3R,4R,5S)-2,5-bis-(N-(((benzyl)oxy) carbonyl) amino) -3,4-epoxy-1,6-diphenylhexane in 600 ml of THF was treated under N2 atmosphere with 13 g (0.36 mol) of sodium borohydride.. The resulting mixture was treated dropwise with 27.7 ml (0.36 mol) of trifluoroacetic acid.. After being stirred for 3.5 h at ambient temperature, the resulting mixture was quenched with 1N aqueous HCl, diluted with water, and stirred for 16 h. The resulting mixture was filtered, washed with water, and dried to provide 22.85 g (58percent) of the desired compound as a white solid.
环氧化合物和醇反应可以得到邻烷氧基醇示例
To a solution of sodium (0.12 g) in benzyl alcohol (3.69 g) was added 1-tert-butoxy-carbonyl-3,4-epoxypyrrolidine (1.07 g) and the mixture stirred at 60.deg. C. for 15 hours.water was added and the mixture extracted with dichloromethane.The organic extract was dried (magnesium sulphate) and evaporated down under reduced pressure.The residue was washed with cold hexane and dried under vacuum to give the title compound (0.88 g) as a white solid. 1H NMR (CDCl3) : 1.46 (s, 9H), 3.25 -3.7 (m, 4H), 3.91 (s, 1H), 4.30 (s, 1H),4.54 (m, 2H), 4.70 (d, 1H), 7.3-7.45 (m, 5H).
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