有机还原剂在1，2-环氧化合物选择性开环反应中的研究
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摘要
环氧乙烷官能团广泛存在于自然界。环氧乙烷的开环产物是有机合成中非常有用的构筑单元。本论文主要研究了利用还原性有机分子对一些合成中有应用价值的环氧的开环反应,并对近年内环氧乙烷类化合物的开环反应进行了简明小结。主要内容有：
一、利用汉斯酯1,4-二氢吡啶这一辅酶NAD(P)H模型化合物为还原剂,有效地实现了2-硝基苯氧甲基环氧乙烷的还原环化反应。在钯碳的催化下,汉斯酯首先将2-硝基苯氧甲基环氧乙烷的硝基还原为氨基,后者对环氧乙烷基团进行分子内亲核开环反应,生成相应的2H-1,4-苯并噁嗪——这一天然产物中广泛存在结构。该反应是辅酶NAD(P)H模型化合物在噁嗪类化合物合成中的第一例应用。
二、用可见光催化实现了α，β-环氧酮向β-羟基酮的温和转化。使用三(2,2＇-双吡啶)钌(Ⅱ)六氟磷酸为光催化剂,用15 W的普通照明用荧光灯即可实现二异丙基乙基胺向α,β-环氧酮的光诱导电子转移反应,以很高的产率生成α,β-环氧酮的开环产物——β-羟基酮。
The 1,2-epoxide functional groups are present extensively in nature. The ring-opening products of the 1,2-epoxide are powerful building blocks in organic synthesis. Besides a concise review on the new progress made in this field in recent years, this thesis focuses on synthetically useful ring-opening reactions of 1, 2-epoxides by employing organic reducing agents. The results are obtained as following:
1. Hantzsch 1,4-dihydropyridine, an analogue of NAD(P)H, was develped as an efficient reduing agent in reductive cyclization of 2-nitrophenoxymethyloxiranes. In the presence of Pd/C as a catalyst, the tandem reduction and intramolecular 1, 2-epoxide opening of substituted 2-nitrophenoxymethyloxiranes gave corresponding 2H-1,4-benzoxazine, a structural subunit of many naturally occurring compounds. It was the first application of model compounds of coenzyme NAD(P)H in the synthesis of oxazinic series.
2. A facile visible light photocatalysis system was employed to transformation ofα,β-epoxyketones toβ-hydroxyketones. Under irradiation by a 15 W fluorescent lamp with Tris(2,2'-bipyridyl)ruthenium(II) hexafluorophosphate as a catalyst, the photoinduced electron transfer reaction from ethyl diisopropyl amine to a,β-epoxyketones took place smoothly and producdβ-hydroxyketones in high yields.
一、利用汉斯酯1,4-二氢吡啶这一辅酶NAD(P)H模型化合物为还原剂,有效地实现了2-硝基苯氧甲基环氧乙烷的还原环化反应。在钯碳的催化下,汉斯酯首先将2-硝基苯氧甲基环氧乙烷的硝基还原为氨基,后者对环氧乙烷基团进行分子内亲核开环反应,生成相应的2H-1,4-苯并噁嗪——这一天然产物中广泛存在结构。该反应是辅酶NAD(P)H模型化合物在噁嗪类化合物合成中的第一例应用。
二、用可见光催化实现了α，β-环氧酮向β-羟基酮的温和转化。使用三(2,2＇-双吡啶)钌(Ⅱ)六氟磷酸为光催化剂,用15 W的普通照明用荧光灯即可实现二异丙基乙基胺向α,β-环氧酮的光诱导电子转移反应,以很高的产率生成α,β-环氧酮的开环产物——β-羟基酮。
The 1,2-epoxide functional groups are present extensively in nature. The ring-opening products of the 1,2-epoxide are powerful building blocks in organic synthesis. Besides a concise review on the new progress made in this field in recent years, this thesis focuses on synthetically useful ring-opening reactions of 1, 2-epoxides by employing organic reducing agents. The results are obtained as following:
1. Hantzsch 1,4-dihydropyridine, an analogue of NAD(P)H, was develped as an efficient reduing agent in reductive cyclization of 2-nitrophenoxymethyloxiranes. In the presence of Pd/C as a catalyst, the tandem reduction and intramolecular 1, 2-epoxide opening of substituted 2-nitrophenoxymethyloxiranes gave corresponding 2H-1,4-benzoxazine, a structural subunit of many naturally occurring compounds. It was the first application of model compounds of coenzyme NAD(P)H in the synthesis of oxazinic series.
2. A facile visible light photocatalysis system was employed to transformation ofα,β-epoxyketones toβ-hydroxyketones. Under irradiation by a 15 W fluorescent lamp with Tris(2,2'-bipyridyl)ruthenium(II) hexafluorophosphate as a catalyst, the photoinduced electron transfer reaction from ethyl diisopropyl amine to a,β-epoxyketones took place smoothly and producdβ-hydroxyketones in high yields.
引文
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