托尼卟吩模型中各结构单元的合成及表征
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摘要
托尼卟吩化合物是一种细菌卟吩类化合物，属于天然环状四吡咯化合物，它在癌症的化学治疗和光动力治疗方面都具有非常的重要意义，其合成和应用研究是目前天然产物化学的重要研究内容和热点。本文通过对卟吩化合物及吡咯类单体化合物的各种合成方法进行分析、比较，为托尼卟吩化合物的全合成路线及其中各结构单体化合物的合成路线的设计提供了依据。
根据“3+1”合成法，设计出托尼卟吩结构模型的全合成路线，对托尼卟吩结构模型B环结构单元3-甲基-3-烯-2-吡咯酮、C环结构单元2-乙氧羰基-3-溴-4-甲基-5-甲酰基吡咯、D环结构单元2-溴-3-甲基-5-甲酰基吡咯以及B-C二咯甲叉化合物2-乙氧羰基-3-溴-4-甲基-5-((4-甲基-5-氧代-1H-吡咯-2(5H-)-甲叉)甲基-1H-吡咯等吡咯衍生物的合成进行了研究，通过元素分析、红外光谱(IR)、~1H核磁共振光谱(NMR)、气相色谱(GC)以及质谱(MS)等检测手段对所合成化合物的结构进行了表征。
吡咯研究结果表明，托尼卟吩结构模型较好地反映了天然托尼卟吩化合物的结构特征。合成所得到的化合物的结构、性能指标与设计要求一致，各目标化合物的合成路线简捷、反应的选择性较好。其中托尼卟吩结构模型C环结构单元和D环结构单元都采用两条合成路线成功获得了目标化合物。各化合物的合成路线设计新颖、方案切实可行。
Tolyporphin is a kind of bacteriochlorins, which belong to natural cyclictetrapyrrole compounds. It plays an important role on chemical treatment and phototherapyof cancer so the research on its synthesis and application is presently an important studycontent and hotspots of the chemistry of natural products. In this dissertation, the methodsto synthesize tolyporphin model and its segments were summarized through the analysisand comparison to various synthesis methods of chlorins and pyrrole derivatives.
The total synthesis way of the tolyporphin model was designed according to the"3+1" synthesis method. The synthesis of several pyrrole derivatives and adipyrrylmethene were studied, such as the ring-B,C,D building block of the tolyporphinmodel——3-methyl-1H-pyrrol-2(5H)-one, ethyl 3-bromo-5-formyl-4-methyl-1H-pyrrole-2-carboxylate and 5-bromo-4-methyl-1H-pyrrole-2-carbaldehyde, and B-C-semichlorinof the tolyporphin model——(Z)-ethyl 3-bromo-4-methyl-5-((4-methyl-5-oxo-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrole-2-carboxylate.The structures of the synthetic productswere characterized by elemental analysis, infrared (IR), ~1H nuclear magnetic resonance(NMR), gas chromatography (GO)and mass spectra (MS).
The results came to the following conclusions: the tolyporphin model reflected thestructural characteristic of natural tolyporphin compounds; the structures and performanceindexes of the products conformed to the design requirement, the synthesis ways of thetarget compounds were brief and had good selectivity; the ring-C,D building block of thetolyporphin model were all synthesized sucessfully by two methods respectively; thesynthesis design of each compound was novel, practical and effective.
根据“3+1”合成法，设计出托尼卟吩结构模型的全合成路线，对托尼卟吩结构模型B环结构单元3-甲基-3-烯-2-吡咯酮、C环结构单元2-乙氧羰基-3-溴-4-甲基-5-甲酰基吡咯、D环结构单元2-溴-3-甲基-5-甲酰基吡咯以及B-C二咯甲叉化合物2-乙氧羰基-3-溴-4-甲基-5-((4-甲基-5-氧代-1H-吡咯-2(5H-)-甲叉)甲基-1H-吡咯等吡咯衍生物的合成进行了研究，通过元素分析、红外光谱(IR)、~1H核磁共振光谱(NMR)、气相色谱(GC)以及质谱(MS)等检测手段对所合成化合物的结构进行了表征。
吡咯研究结果表明，托尼卟吩结构模型较好地反映了天然托尼卟吩化合物的结构特征。合成所得到的化合物的结构、性能指标与设计要求一致，各目标化合物的合成路线简捷、反应的选择性较好。其中托尼卟吩结构模型C环结构单元和D环结构单元都采用两条合成路线成功获得了目标化合物。各化合物的合成路线设计新颖、方案切实可行。
Tolyporphin is a kind of bacteriochlorins, which belong to natural cyclictetrapyrrole compounds. It plays an important role on chemical treatment and phototherapyof cancer so the research on its synthesis and application is presently an important studycontent and hotspots of the chemistry of natural products. In this dissertation, the methodsto synthesize tolyporphin model and its segments were summarized through the analysisand comparison to various synthesis methods of chlorins and pyrrole derivatives.
The total synthesis way of the tolyporphin model was designed according to the"3+1" synthesis method. The synthesis of several pyrrole derivatives and adipyrrylmethene were studied, such as the ring-B,C,D building block of the tolyporphinmodel——3-methyl-1H-pyrrol-2(5H)-one, ethyl 3-bromo-5-formyl-4-methyl-1H-pyrrole-2-carboxylate and 5-bromo-4-methyl-1H-pyrrole-2-carbaldehyde, and B-C-semichlorinof the tolyporphin model——(Z)-ethyl 3-bromo-4-methyl-5-((4-methyl-5-oxo-1H-pyrrol-2(5H)-ylidene)methyl)-1H-pyrrole-2-carboxylate.The structures of the synthetic productswere characterized by elemental analysis, infrared (IR), ~1H nuclear magnetic resonance(NMR), gas chromatography (GO)and mass spectra (MS).
The results came to the following conclusions: the tolyporphin model reflected thestructural characteristic of natural tolyporphin compounds; the structures and performanceindexes of the products conformed to the design requirement, the synthesis ways of thetarget compounds were brief and had good selectivity; the ring-C,D building block of thetolyporphin model were all synthesized sucessfully by two methods respectively; thesynthesis design of each compound was novel, practical and effective.
引文
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