摘要
随着科学技术的进步和人民生活水平的不断提高,人们对材料、信息和能源的要求也越来越高。而材料是科学和工业技术发展的基础和先导,新材料是各种新的科学技术及改造传统工业技术的物质基础,一种新材料的出现和使用往往会给技术进步、新行业的形成乃至整个经济和社会的发展带来巨大变化。
由于螺环化合物的独特结构和特点,使其功能和应用也越来越广泛。因此,人们对螺环化合物研究和认识也越来越深入,其多种新优点和优势也将被陆续发现。不管是含有螺环结构的树状大分子化合物还是含有手性轴的螺环化合物,都将更广泛的被研究和应用,给人类的生产、生活等带来更大的帮助,加速人类社会的发展速度,对人类社会的进步产生深远的影响。
本论文主要由以下几部分组成:
1合成出了螺环三代树状大分子化合物(17)。
首先,以4,4′-二环己二酮单缩乙二醇为最初原料,合成出了化合物(1),α,β,γ,δ-四[4-(4-氧代环己烷基)环己叉]卟啉(6)。同时根据文献资料,合成了1,3-茚二酮,接着在浓硫酸中,100℃下经芳构化反应,合成出了三聚茚-5,10,15-三酮(9)。
其次,将化合物(1)在CaO存在的条件下,利用羟醛缩合与Cannizzaro反应合成出了化合物化合物(16)。
在次,以对苯二甲醛为原料,经过四步反应,最终合成出3-[4-(2,2-二氰基)乙烯基苯基]-9-(4-甲酰基苯基)-2,4,8,10-四氧杂-螺[5.5]-十一烷(12)。
最后,我们用化合物(12),在酸性条件下,与化合物(16)进行缩醛反应,得到了最后的目标化合物(17)。
2合成出了三种具有手性轴的多螺环化合物3,15-双{8-(1,4-二氧杂螺[4.5]癸烷基)}-7,11,18,21-四氧杂三螺[5.2.2.5.2.2]二十一烷(18)、3,15-(4-(二氰基亚甲基环己烷基))-7,11,18,21-四氧杂三螺[5.2.2.5.2.2]二十一烷(19)和3,15-聚{7,11,18,21-四氧杂三螺[5.2.2.5.2.2]二十一烷}(20)。同时根据文献资料又合成出了不具有手性轴的化合物7,11,18,21-四氧杂三螺[5.2.2.5.2.2]二十一烷(21)。通过对比,讨论了多螺环手性化合物手性环境的变化规律。
3分别采用水和正丁醇做溶剂,制备出了三种多羟基化合物:2,2,6,6-四羟甲基环己醇(22)、2,2,3,3,5,5,6,6-八羟基甲基-1,4-环己二醇(23)和3,3,3′,3′,5,5,5′,5′-八羟甲基-4,4′-二环己二醇(24),并对其反应机理和条件进行了相关讨论。
然后,以这三种多羟基化合物为原料,在酸性条件下合成出了多种缩醛酮类的化合物。
中间体和产物进行了IR,~1H-NMR等结构表征。
People will have a higher quality requirement to material,information and energy,with the progress in science and the living standard.What's more,material is the precursor and foundation in the fields of industry and technology.As a foundation,new materials always speed up rebuilding different technologies and traditional industries.One kind of new material also brings the huge changes in technology,economy and even the whole world.
The spiro-compounds have a wide range between function and their applications,because of its unique structure.As the study on the spiro-compounds become much deeper,more and more advantages also will be found.So the dendrimers including the spiro and the chiral multi-spiro compounds will have a better investigation and application in the future.In the meantime,the development and progress of our society will be speeded up.
The thesis was made up of several parts as follows:
1.The dendritic compound(17) including the spiro was prepared.
Firstly,compound(1) and(6) was prepared using the 4-(1,4-dioxaspiro[4.5]decan-8-yl) cyclohexanone as the raw material.And then compound(9) was also prepared using the 1H-in dene-1,3(2H)-dione prepared according to the reference.
Secondly,compound(16) was synthesized by the reaction of compound(1) with trioxymethylene in the presence of calcium hydroxide.
Thirdly,2-(4-(9-(4-formylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-3-yl)benzylidene) malononitrile(12) was prepared using terephthalaldehyde as the raw material through four steps.
Finally,compound(17) was synthesized by the reaction of(12) with(16) in the presence of acid.
2.3,15-bi {8-(1,4-dioxaspiro[4.5]decyl)}-7,11,18,21-tetraoxatrispiro[5.2.2.5.2.2]heneicosane (18),3,15-(4-(bicyanomethylenecyclohexyl))-7,11,18,21-tetraoxatrispiro[5.2.2.5.2.2]heneicos ane(19) and 3,15-poly{7,11,18,21- tetraoxatrispiro[5.2.2.5.2.2]heneicosane(20) including chiral axis were prepared separately,and then 7,11,18,21-tetra- oxatrispiro[5.2.2.5.2.2]heneicos ane(21) was also prepared according to the reference.At last,the ~1HNMR law of multi-spiro chiral compounds was investigated in the thesis.
3.2,2,6,6-tetrahydroxymethylcyclohexanol(22),2,2,3,3,5,5,6,6-octohydroxymethylcy-1,4-c yclohexanediol(23) and 3,3,3',3',5,5,5',5'-octohydroxymethylcy-4,4'-bicycloh-exanediol(24) were prepared separately following several acetal compounds synthesized by(22),(23) and (24).
The compounds was characterized by IR,~1H-NMR et al.
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