芴衍生物及含芴环甾体化合物的合成研究
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摘要
本论文主要包括芴衍生物和含芴环甾体化合物的合成研究。
一、芴衍生物的合成研究：
溴代芴酮、硝基芴酮及溴代硝基芴酮作为煤焦油分离产品芴的衍生物,被广泛应用于医药、塑料、染料及光电功能材料等领域,在世界范围内的需求量日益增大,对其制备工艺技术的开发也一直是研究热点。但国内外现有生产制备技术存在种种不足,比如产率低、成本高、反应物分离纯化困难以及环境污染大等,不易实现工业化。本论文针对现有合成工艺的缺陷,对芴类衍生物的合成工艺进行了优化研究。
研究内容：(1)以芴为原料,通过氧化、溴代、硝化等反应制备溴代芴酮、硝基芴酮及溴代硝基芴酮,包括芴酮、2-溴芴酮、2-硝基芴酮、2,4,7-三硝基芴酮、2,7-二硝基芴酮、2-溴-7-硝基芴酮及2,7-二溴-7-硝基芴酮7种化合物的合成。通过正交试验确定以下工艺参数：a.最佳反应时间和反应温度；b.最佳原料的配比。对上述其中5种芴衍生物的综合实验条件进行了优化,所优化的工艺采用空气氧化、水为溶剂等绿色节能技术,具有绿色高效、成本低廉、操作简便等创新优势,易于实现工业化,为进一步放大生产研究提供了理论依据及工艺技术参数。为了配合合成实验需要,本论文探索建立了反相高效液相色谱法对产物2,7-二溴-4-硝基芴酮及其原料2,7-二溴芴酮、副产物芴酮衍生物的定性、定量分析方法,取得了较好的结果。(2)依据本论文在合成硝基芴酮类化合物时所开发的以水为溶剂的新型液-液体系硝化方法,本论文对以溴苯为原料制备2,4-二硝基-溴苯的硝化反应进行了综合实验条件的优化,取得了较好的反应效果。
二、含芴环甾体化合物的合成研究：
胆甾醇等甾体化合物广泛存在于自然界,含量丰富。因其具有的结构特点被作为合成基元用于制备各种功能材料,广泛应用于化妆品、液晶材料、凝胶剂、医药、人造膜等领域,具有重要的学术价值和应用前景。芴类化合物作为煤焦油的下游产品,是医药、塑料、染料及光电功能材料等的重要原料,应用十分广泛。然而,将甾体化合物与芴类化合物结合在一起的研究尚未见文献报道。
本论文设计合成了新型的含芴环甾体化合物,所合成的化合物有望应用于液晶材料、凝胶剂及分子标记等领域。具体研究内容是：以胆甾醇和2,7-二溴-4-硝基-芴酮为原料合成含芴环甾体化合物2-胆甾醚基-7-溴-4-硝基芴酮,再进行还原反应制备可进行聚合反应的单体2-胆甾醚基-7-溴-4-氨基-9-芴醇,并对各步单元反应进行了条件优化。
此外,作为重要的有机功能材料,聚芳胺类化合物在材料科学和高分子化学中具有重要的应用价值,可作为半导体器件、导电材料和有机电致发光材料和光致发光材料以及光、磁记录材料等而广泛使用。在上述研究中,新型聚合物单体的设计与合成具有重要意义。本论文以胆甾醇和2,4-二硝基溴苯为原料合成了2,4-二硝基苯基胆甾醚,再进行还原反应制备出聚苯胺单体4-胆甾基-1,3-苯二胺,并对相转移催化下的成醚反应进行了条件优化。
This paper includes studies on the synthesis of fluorene derivatives and steroids containing fluorene ring.
1. Synthesis of fluorene derivatives:
Bromo-, nitro-, and bromonitrofluorenones as derivatives of fluorene, which is separated from coal tar, are widely used in areas such as medicinal and pharmaceutical agents, plastic additives, organic dyes and organic light-emitting materials. As the worldwide demand increases, the exploration of their preparation methods remains research focus. However, the current preparation methods at home and abroad have various disadvantages including low yield, high costs, difficult separation, environmental pollution and difficult industrialization. Based on the defects of these current preparation methods, this paper developed and optimized the preparation methods for fluorene derivatives.
Research content:(1) Bromo-, nitro-, and bromonitrofluorenones were synthesized from fluorene through oxidation, bromination and nitration, including 7 compounds as fluorenone,2-bromofluorenone,2-nitro-fluorenone,2,4,7-trinitro-fluorenone,2,7-dinitrofluorenone,2-bromo-7-nitro-fluorenone and 2,7-dibromo-4-nitro-fluorenone. The process parameters were determined by orthogonal experiment as follows:a. the best reaction time and temperature; b. the best ratio among starting materials. The comprehensive experiment conditions of 5 compounds above were optimized, and the optimal preparation methods use green technologies like air oxidation, water as solvent, hence poccessing innovative superiorities of being cost-effective, easy-to-operate, and easy to be industrialized. The newly-developed synthetic methods provide the theoretical foundation and processing parameters for further amplified synthesis research. In order to coordinate the need of synthetic work, this paper explores and establishs a qualitative and quantitative determination method for 2,7-dibromo-4 -nitro-fluorenone,2,7-dibromo-fluorenone and fluorenone derivatives by reverse high performance liquid chromatography. (2) Based on the new liquid-liquid nitration method developed in the preparation of nitrofluorenones, the comprehensive experiment conditions of nitration of bromobenzene to synthesize 2,4-dinitro-l-bromo-benzene were optimized and it obtained good reaction result.
2. Synthesis of steroids containing fluorene:
Cholesterol and other steroid compounds were widely distributed in nature with abundance. For their structural characteristics, they are used as synthetic building block to synthesize many functional materials, and have braod applications in cosmetics and toiletries, liquid crystals, organogel, artificial membrane and medical fields with importand academic value and application prospect. Fluorene derivatives as downstream products from coal tar are importand building blocks in the synthesis of medicinal and pharmaceutical agents, plastic additives, organic dyes and organic light-emitting materials. However, there is no document reporting the combination of the two compounds.
This paper designs and synthesizes new compounds of steroid containing fluorene ring, which may have the potential application in liquid crystals, organogel and molecular marker fields. The research content is as follows:2-cholesteryl-7-bromo-4-nitro-fluorenone was synthesized from cholesterol and 2,7-dibromo-4-nitro-fluorenone and then reduced to monomer 2-cholesteryl-7-bromo-4-amino-9-fluorenol, the experiment conditions of each step were optimized.
Besides, poly-aromatic amine compounds as important organic functional materials have important application in materials and polymer chemistry, ranging from semiconductor device, conductive material, organic electroluminescent material, photoluminescent material to light and magnetic recording fields. In the above studies, it is important to design and synthesize new monomers. In this paper,4-cholesteryl-1,3-dinitro-benzene was synthesized from cholesterol and 2,4-dinitro-1-bromo-benzene and then reduced to monomer 4-cholesteryl-1,3-diamino-benzene, and the experiment conditions of phase transfer catalysed etherification were optimized.
一、芴衍生物的合成研究：
溴代芴酮、硝基芴酮及溴代硝基芴酮作为煤焦油分离产品芴的衍生物,被广泛应用于医药、塑料、染料及光电功能材料等领域,在世界范围内的需求量日益增大,对其制备工艺技术的开发也一直是研究热点。但国内外现有生产制备技术存在种种不足,比如产率低、成本高、反应物分离纯化困难以及环境污染大等,不易实现工业化。本论文针对现有合成工艺的缺陷,对芴类衍生物的合成工艺进行了优化研究。
研究内容：(1)以芴为原料,通过氧化、溴代、硝化等反应制备溴代芴酮、硝基芴酮及溴代硝基芴酮,包括芴酮、2-溴芴酮、2-硝基芴酮、2,4,7-三硝基芴酮、2,7-二硝基芴酮、2-溴-7-硝基芴酮及2,7-二溴-7-硝基芴酮7种化合物的合成。通过正交试验确定以下工艺参数：a.最佳反应时间和反应温度；b.最佳原料的配比。对上述其中5种芴衍生物的综合实验条件进行了优化,所优化的工艺采用空气氧化、水为溶剂等绿色节能技术,具有绿色高效、成本低廉、操作简便等创新优势,易于实现工业化,为进一步放大生产研究提供了理论依据及工艺技术参数。为了配合合成实验需要,本论文探索建立了反相高效液相色谱法对产物2,7-二溴-4-硝基芴酮及其原料2,7-二溴芴酮、副产物芴酮衍生物的定性、定量分析方法,取得了较好的结果。(2)依据本论文在合成硝基芴酮类化合物时所开发的以水为溶剂的新型液-液体系硝化方法,本论文对以溴苯为原料制备2,4-二硝基-溴苯的硝化反应进行了综合实验条件的优化,取得了较好的反应效果。
二、含芴环甾体化合物的合成研究：
胆甾醇等甾体化合物广泛存在于自然界,含量丰富。因其具有的结构特点被作为合成基元用于制备各种功能材料,广泛应用于化妆品、液晶材料、凝胶剂、医药、人造膜等领域,具有重要的学术价值和应用前景。芴类化合物作为煤焦油的下游产品,是医药、塑料、染料及光电功能材料等的重要原料,应用十分广泛。然而,将甾体化合物与芴类化合物结合在一起的研究尚未见文献报道。
本论文设计合成了新型的含芴环甾体化合物,所合成的化合物有望应用于液晶材料、凝胶剂及分子标记等领域。具体研究内容是：以胆甾醇和2,7-二溴-4-硝基-芴酮为原料合成含芴环甾体化合物2-胆甾醚基-7-溴-4-硝基芴酮,再进行还原反应制备可进行聚合反应的单体2-胆甾醚基-7-溴-4-氨基-9-芴醇,并对各步单元反应进行了条件优化。
此外,作为重要的有机功能材料,聚芳胺类化合物在材料科学和高分子化学中具有重要的应用价值,可作为半导体器件、导电材料和有机电致发光材料和光致发光材料以及光、磁记录材料等而广泛使用。在上述研究中,新型聚合物单体的设计与合成具有重要意义。本论文以胆甾醇和2,4-二硝基溴苯为原料合成了2,4-二硝基苯基胆甾醚,再进行还原反应制备出聚苯胺单体4-胆甾基-1,3-苯二胺,并对相转移催化下的成醚反应进行了条件优化。
This paper includes studies on the synthesis of fluorene derivatives and steroids containing fluorene ring.
1. Synthesis of fluorene derivatives:
Bromo-, nitro-, and bromonitrofluorenones as derivatives of fluorene, which is separated from coal tar, are widely used in areas such as medicinal and pharmaceutical agents, plastic additives, organic dyes and organic light-emitting materials. As the worldwide demand increases, the exploration of their preparation methods remains research focus. However, the current preparation methods at home and abroad have various disadvantages including low yield, high costs, difficult separation, environmental pollution and difficult industrialization. Based on the defects of these current preparation methods, this paper developed and optimized the preparation methods for fluorene derivatives.
Research content:(1) Bromo-, nitro-, and bromonitrofluorenones were synthesized from fluorene through oxidation, bromination and nitration, including 7 compounds as fluorenone,2-bromofluorenone,2-nitro-fluorenone,2,4,7-trinitro-fluorenone,2,7-dinitrofluorenone,2-bromo-7-nitro-fluorenone and 2,7-dibromo-4-nitro-fluorenone. The process parameters were determined by orthogonal experiment as follows:a. the best reaction time and temperature; b. the best ratio among starting materials. The comprehensive experiment conditions of 5 compounds above were optimized, and the optimal preparation methods use green technologies like air oxidation, water as solvent, hence poccessing innovative superiorities of being cost-effective, easy-to-operate, and easy to be industrialized. The newly-developed synthetic methods provide the theoretical foundation and processing parameters for further amplified synthesis research. In order to coordinate the need of synthetic work, this paper explores and establishs a qualitative and quantitative determination method for 2,7-dibromo-4 -nitro-fluorenone,2,7-dibromo-fluorenone and fluorenone derivatives by reverse high performance liquid chromatography. (2) Based on the new liquid-liquid nitration method developed in the preparation of nitrofluorenones, the comprehensive experiment conditions of nitration of bromobenzene to synthesize 2,4-dinitro-l-bromo-benzene were optimized and it obtained good reaction result.
2. Synthesis of steroids containing fluorene:
Cholesterol and other steroid compounds were widely distributed in nature with abundance. For their structural characteristics, they are used as synthetic building block to synthesize many functional materials, and have braod applications in cosmetics and toiletries, liquid crystals, organogel, artificial membrane and medical fields with importand academic value and application prospect. Fluorene derivatives as downstream products from coal tar are importand building blocks in the synthesis of medicinal and pharmaceutical agents, plastic additives, organic dyes and organic light-emitting materials. However, there is no document reporting the combination of the two compounds.
This paper designs and synthesizes new compounds of steroid containing fluorene ring, which may have the potential application in liquid crystals, organogel and molecular marker fields. The research content is as follows:2-cholesteryl-7-bromo-4-nitro-fluorenone was synthesized from cholesterol and 2,7-dibromo-4-nitro-fluorenone and then reduced to monomer 2-cholesteryl-7-bromo-4-amino-9-fluorenol, the experiment conditions of each step were optimized.
Besides, poly-aromatic amine compounds as important organic functional materials have important application in materials and polymer chemistry, ranging from semiconductor device, conductive material, organic electroluminescent material, photoluminescent material to light and magnetic recording fields. In the above studies, it is important to design and synthesize new monomers. In this paper,4-cholesteryl-1,3-dinitro-benzene was synthesized from cholesterol and 2,4-dinitro-1-bromo-benzene and then reduced to monomer 4-cholesteryl-1,3-diamino-benzene, and the experiment conditions of phase transfer catalysed etherification were optimized.
引文
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