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酚类

酚类是一大类化合物,它们主要特征是分子中含有一个羟基(-OH)直接连接在苯环上。这类化合物广泛存在于自然界中,并且具有重要的生物、医药及工业应用价值。

结构与分类

酚类化合物的基本结构为苯环上的氧原子与羟基相连。根据羟基的位置不同,可将酚分为单酚和多酚两大类:

  • 单酚:每个分子仅有一个酚羟基。
  • 多酚:含有两个或多个酚羟基的化合物。
生物学意义
  1. 天然来源:酚广泛存在于植物、动物以及微生物中,如咖啡因中的茶酚、儿茶素等。
  2. 抗氧化作用:许多酚类物质具有较强的抗氧化性,能够清除体内的自由基,保护细胞免受氧化损伤。
  3. 抗菌活性:部分酚类化合物展示出显著的抗菌效果,可用于食品保鲜或开发抗生素。
工业应用
  1. 农药和杀虫剂:利用某些酚类化合物对特定昆虫的选择性毒性进行害虫控制。
  2. 染料工业:许多天然及合成染料都基于酚结构设计而成。
  3. 医药领域:作为原料或药物成分,例如阿司匹林的核心成分水杨酸就属于苯酚衍生物。
工业生产

酚类可以通过多种途径制备:

  • 通过煤焦油蒸馏或石油裂解得到的粗酚进行精炼获得。
  • 以苯或其他芳烃为原料,在催化剂作用下与水反应生成苯酚,此过程称为菲林斯勒反应(Fischer–Strassmann反应)。
注意事项

尽管酚类化合物具有广泛的应用前景,但它们也可能带来毒性问题。例如强酸性的酚类物质会对皮肤造成刺激甚至腐蚀。因此在使用时需注意安全防护措施。

以上是对酚类的简单介绍,涵盖了其基本定义、生物学意义及工业应用等方面的内容。

中文名称 英文名称 CAS号 化学式 结构式图片
—— (R)-3-(1-hydroxyethyl)phenol —— C8H10O2
(R)-3-(1-hydroxyethyl)phenol
—— 4-hydroxy-3-methoxyphenylpropanal 1192280-94-6 C10H12O3
4-hydroxy-3-methoxyphenylpropanal
—— 1-(4-hydroxy-3-methoxyphenyl)propyl acetate —— C12H16O4
1-(4-hydroxy-3-methoxyphenyl)propyl acetate
—— 2-(((6-methylpyridin-2-yl)imino)methyl)phenol 59129-91-8 C13H12N2O
2-(((6-methylpyridin-2-yl)imino)methyl)phenol
—— tert-butyl (adamantan-2-ylmethyl)(2-hydroxyphenethyl)carbamate —— C24H35NO3
tert-butyl (adamantan-2-ylmethyl)(2-hydroxyphenethyl)carbamate
—— N-(1-deoxy-D-fructos-1-yl)dopamine —— C14H21NO7
N-(1-deoxy-D-fructos-1-yl)dopamine
—— N-(3-methoxy-4-hydroxybenzyl)-N-methylnonanamide —— C18H29NO3
N-(3-methoxy-4-hydroxybenzyl)-N-methylnonanamide
—— 8-Hydroxynonivamide —— C17H27NO4
8-Hydroxynonivamide
—— 3-chloro-6-(salicylidenehydrazinyl)pyridazine —— C11H9ClN4O
3-chloro-6-(salicylidenehydrazinyl)pyridazine
—— (S)-1-(3-hydroxyphenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium bromide 1412902-90-9 Br*C18H24NO
(S)-1-(3-hydroxyphenyl)-N,N-dimethyl-N-((S)-1-phenylethyl)ethanaminium bromide
—— 2,4-dimethoxy-N-(2-hydroxy-3-methoxybenzylidene)benzenamine —— C16H17NO4
2,4-dimethoxy-N-(2-hydroxy-3-methoxybenzylidene)benzenamine
—— 2-amino-5-(3-hydroxy-4-methoxy-benzylidene)-1-methyl-1,5-dihydro-imidazol-4-one —— C12H13N3O3
2-amino-5-(3-hydroxy-4-methoxy-benzylidene)-1-methyl-1,5-dihydro-imidazol-4-one
—— 2-amino-5-(4-hydroxy-3,5-dimethoxy-benzylidene)-1-methyl-1,5-dihydro-imidazol-4-one —— C13H15N3O4
2-amino-5-(4-hydroxy-3,5-dimethoxy-benzylidene)-1-methyl-1,5-dihydro-imidazol-4-one
—— N,N'-disalicylidene-2,6-diaminopyridine —— C19H15N3O2
N,N'-disalicylidene-2,6-diaminopyridine
—— (E)-4-[(2-hydroxyphenyl)imino]pentan-2-one —— C11H13NO2
(E)-4-[(2-hydroxyphenyl)imino]pentan-2-one
—— 2-(4-hydroxyphenyl)ethyl acrylate —— C11H12O3
2-(4-hydroxyphenyl)ethyl acrylate
—— tetrachloroiodophenol —— C6HCl4IO
tetrachloroiodophenol
—— 2-methoxy-6-(N-morpholinyl)methylphenol —— C12H17NO3
2-methoxy-6-(N-morpholinyl)methylphenol
—— threo-4-hydroxy-N-methyl-methylphenidate —— C15H21NO3
threo-4-hydroxy-N-methyl-methylphenidate
—— (S)-metoprolol succinic acid —— C4H6O4*2C15H25NO3
(S)-metoprolol succinic acid
—— succinic acid bis-(4-hydroxy-phenethyl ester) —— C20H22O6
succinic acid bis-(4-hydroxy-phenethyl ester)
—— 2-cyclohexyl-2-(2-hydroxy-6-methylphenyl)aminoacetonitrile —— C15H20N2O
2-cyclohexyl-2-(2-hydroxy-6-methylphenyl)aminoacetonitrile
—— 2,2-dimethyl-1-(2-hydroxy-6-methylphenyl)aminopropane-1-carbonitrile —— C13H18N2O
2,2-dimethyl-1-(2-hydroxy-6-methylphenyl)aminopropane-1-carbonitrile
—— 1-(2-hydroxy-6-methylphenyl)aminononane-1-carbonitrile —— C17H26N2O
1-(2-hydroxy-6-methylphenyl)aminononane-1-carbonitrile
—— (R)-3,4-dihydroxymandelonitrile 190383-25-6 C8H7NO3
(R)-3,4-dihydroxymandelonitrile
—— ZINC00039089 —— C9H13NO3*H
ZINC00039089
—— 7-hydroxy-1-(4-methyl-1-piperazinyl)-2,3-dihydronaphthalene —— C15H20N2O
7-hydroxy-1-(4-methyl-1-piperazinyl)-2,3-dihydronaphthalene
—— (E)-3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)-N-(2-mercaptoethyl)propanamide —— C11H13BrN2O3S
(E)-3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)-N-(2-mercaptoethyl)propanamide
—— hydroxytyrosol tris(methyl carbonate) —— C14H16O9
hydroxytyrosol tris(methyl carbonate)
—— 1,3,5-cis-tris((2-hydroxy-5-methoxybenzyl)amino)cyclohexane —— C30H39N3O6
1,3,5-cis-tris((2-hydroxy-5-methoxybenzyl)amino)cyclohexane
—— 3-(2-hydroxy-5-nitro-phenylimino)-1,3-dihydroindol-2-one —— C14H9N3O4
3-(2-hydroxy-5-nitro-phenylimino)-1,3-dihydroindol-2-one
—— 1,3,5-cis-tris((2-hydroxy-5-nitrobenzyl)amino)cyclohexane —— C27H30N6O9
1,3,5-cis-tris((2-hydroxy-5-nitrobenzyl)amino)cyclohexane
—— ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate —— C11H12F2O3
ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate
—— 4-hydroxy-2-(3-hydroxypropyl)-5-methoxyisophthalaldehyde —— C12H14O5
4-hydroxy-2-(3-hydroxypropyl)-5-methoxyisophthalaldehyde
—— 4-chloro-3,5-(dimethyl-D6)-phenol —— C8H9ClO
4-chloro-3,5-(dimethyl-D6)-phenol
—— 2-bromo-4-(pentafluorosulfanyl)phenol —— C6H4BrF5OS
2-bromo-4-(pentafluorosulfanyl)phenol
—— 6-benzyl-3-(4-hydroxyphenyl)thiazolo[3,2-b]-1,2,4-triazin-7-one —— C18H13N3O2S
6-benzyl-3-(4-hydroxyphenyl)thiazolo[3,2-b]-1,2,4-triazin-7-one
—— trans-6,7-Dihydro-7-(4-hydroxy-3-methoxyphenyl)-4,9-dimethoxy-2,11-dipropyldibenzo<e,g><1,4>dioxocin-6-ylmethanol —— C30H36O7
trans-6,7-Dihydro-7-(4-hydroxy-3-methoxyphenyl)-4,9-dimethoxy-2,11-dipropyldibenzo<e,g><1,4>dioxocin-6-ylmethanol
—— (R)-tert-butyl (3-hydroxy-3-(3-hydroxyphenyl)propyl)carbamate —— C14H21NO4
(R)-tert-butyl (3-hydroxy-3-(3-hydroxyphenyl)propyl)carbamate
—— threo-1-(4-hydroxy-3-methoxyphenyl)-1-methoxy-2-<2-methoxy-4-(3-hydroxy-1-propenyl)phenoxy>-3-hydroxypropane —— C21H26O7
threo-1-(4-hydroxy-3-methoxyphenyl)-1-methoxy-2-<2-methoxy-4-(3-hydroxy-1-propenyl)phenoxy>-3-hydroxypropane
—— 5-chloro-4-nitrobenzene-1,3-diol —— C6H4ClNO4
5-chloro-4-nitrobenzene-1,3-diol
—— rac-gnetifolin F —— C25H24O7
rac-gnetifolin F
—— 4,4'-((1E,4E)-penta-1,4-diene-1,5-diyl)bis(2-methoxyphenol) —— C19H20O4
4,4'-((1E,4E)-penta-1,4-diene-1,5-diyl)bis(2-methoxyphenol)
—— coniferyl stearate —— C28H46O4
coniferyl stearate
—— 1,2-bis(2',4'-dihydroxyphenylthio)ethane —— C14H14O4S2
1,2-bis(2',4'-dihydroxyphenylthio)ethane
—— 2-iminobenzo[d][1,3]oxathiol-6-ol —— C7H5NO2S
2-iminobenzo[d][1,3]oxathiol-6-ol
—— 3-isopropyl-5-[4-(2-methoxyethyl)phenoxymethyl]oxazolidine —— C16H25NO3
3-isopropyl-5-[4-(2-methoxyethyl)phenoxymethyl]oxazolidine
—— N-isopropyl-3-<<4'-(2''-methoxyethyl)phenyl>oxy>-2-oxo-1-propylamine —— C15H23NO3
N-isopropyl-3-<<4'-(2''-methoxyethyl)phenyl>oxy>-2-oxo-1-propylamine
—— 1-(3-ethoxy-4-hydroxyphenyl)-5-hydroxydodecan-3-one —— C20H32O4
1-(3-ethoxy-4-hydroxyphenyl)-5-hydroxydodecan-3-one
—— N-succinyltyramine —— C12H15NO4
N-succinyltyramine