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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
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one —— C20H18N2O4S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-hydroxyphenyl)imino-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid —— C16H17NO5S2
2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]pentanoic acid
—— (2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C21H22N2O5S
(2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (2Z)-2-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]-3-oxo-3-pyrrolidin-1-ylpropanenitrile —— C23H19N3O4S
(2Z)-2-[(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]-3-oxo-3-pyrrolidin-1-ylpropanenitrile
—— (2Z,5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C20H19BrN2O4S
(2Z,5Z)-5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— (2Z,5Z)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-3-(2-ethoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one —— C20H18BrClN2O3S
(2Z,5Z)-5-(3-bromo-5-chloro-4-hydroxybenzylidene)-3-(2-ethoxyethyl)-2-(phenylimino)-1,3-thiazolidin-4-one
—— ethyl (2Z)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-morpholin-4-yl-2-oxoethyl)-4-oxo-1,3-thiazolidin-2-ylidene]acetate —— C21H24N2O7S
ethyl (2Z)-2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-morpholin-4-yl-2-oxoethyl)-4-oxo-1,3-thiazolidin-2-ylidene]acetate
—— (5Z)-3-(3-hydroxyphenyl)-5-(1H-pyrrol-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H10N2O2S2
(5Z)-3-(3-hydroxyphenyl)-5-(1H-pyrrol-2-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-2-(5-chloro-2-hydroxyphenyl)imino-5-[(E)-3-(furan-2-yl)prop-2-enylidene]-1,3-thiazolidin-4-one —— C16H11ClN2O3S
(5Z)-2-(5-chloro-2-hydroxyphenyl)imino-5-[(E)-3-(furan-2-yl)prop-2-enylidene]-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(2,5-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-2-(2,5-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methoxyphenyl)-1,3-thiazolidine-2,4-dione —— C18H15NO5S
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-methoxyphenyl)-1,3-thiazolidine-2,4-dione
—— (5Z)-2-(2,5-dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H18N2O3S
(5Z)-2-(2,5-dimethylphenyl)imino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— N-(2-hydroxy-4-nitrophenyl)-2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C21H17N3O5S2
N-(2-hydroxy-4-nitrophenyl)-2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— N-(2-hydroxy-5-nitrophenyl)-4-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C23H21N3O5S2
N-(2-hydroxy-5-nitrophenyl)-4-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— N-(2-hydroxy-4-nitrophenyl)-4-[(5Z)-4-oxo-5-[(E)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide —— C22H19N3O5S2
N-(2-hydroxy-4-nitrophenyl)-4-[(5Z)-4-oxo-5-[(E)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamide
—— N-(2-hydroxy-4-nitrophenyl)-2-[(5Z)-4-oxo-5-[(E)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C20H15N3O5S2
N-(2-hydroxy-4-nitrophenyl)-2-[(5Z)-4-oxo-5-[(E)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— (5R)-5-hydroxy-3-(2-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one —— C14H16O4
(5R)-5-hydroxy-3-(2-hydroxy-3-methoxyphenyl)-5-methylcyclohex-2-en-1-one
—— (5Z)-3-hexyl-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C17H21NO3S2
(5Z)-3-hexyl-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-3-(2-ethylphenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one —— C19H17NO3S2
(5Z)-3-(2-ethylphenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— (5Z)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-3-(3-nitrobenzyl)-1,3-thiazolidine-2,4-dione —— C17H10BrN3O7S
(5Z)-5-(3-bromo-4-hydroxy-5-nitrobenzylidene)-3-(3-nitrobenzyl)-1,3-thiazolidine-2,4-dione
—— (4E)-2-(2-bromophenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one —— C16H9BrN2O5
(4E)-2-(2-bromophenyl)-4-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-oxazol-5-one
—— 1-[(3S,4R)-4-chloro-1,1-dioxothiolan-3-yl]-3-(2-hydroxy-4-nitrophenyl)thiourea —— C11H12ClN3O5S2
1-[(3S,4R)-4-chloro-1,1-dioxothiolan-3-yl]-3-(2-hydroxy-4-nitrophenyl)thiourea
—— 1-[(3S)-1,1-dioxothiolan-3-yl]-3-(2-hydroxy-4-nitrophenyl)thiourea —— C11H13N3O5S2
1-[(3S)-1,1-dioxothiolan-3-yl]-3-(2-hydroxy-4-nitrophenyl)thiourea
—— 4-[(S)-4,5-dihydro-1H-imidazol-2-yl-(4-methylpiperazin-1-yl)methyl]phenol —— C15H22N4O
4-[(S)-4,5-dihydro-1H-imidazol-2-yl-(4-methylpiperazin-1-yl)methyl]phenol
—— (5Z)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,6-dimethylphenyl)imino-3-phenyl-1,3-thiazolidin-4-one —— C25H20Br2N2O3S
(5Z)-5-[(2,3-dibromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(2,6-dimethylphenyl)imino-3-phenyl-1,3-thiazolidin-4-one
—— 5-(2-Bromo-5-hydroxybenzylidene)-3-(2-methylphenyl)-2-[(2-methylphenyl)imino]-1,3-thiazolidin-4-one —— C24H19BrN2O2S
5-(2-Bromo-5-hydroxybenzylidene)-3-(2-methylphenyl)-2-[(2-methylphenyl)imino]-1,3-thiazolidin-4-one
—— 4-[(R)-4,5-dihydro-1H-imidazol-2-yl-(4-methylpiperazin-1-yl)methyl]phenol —— C15H22N4O
4-[(R)-4,5-dihydro-1H-imidazol-2-yl-(4-methylpiperazin-1-yl)methyl]phenol
—— 1-(2-hydroxy-4-nitrophenyl)-3-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]urea —— C12H15N3O6S
1-(2-hydroxy-4-nitrophenyl)-3-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]urea
—— (5Z)-2-[(2,4-dimethoxyphenyl)amino]-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4(5H)-one —— C19H18N2O5S
(5Z)-2-[(2,4-dimethoxyphenyl)amino]-5-(4-hydroxy-3-methoxybenzylidene)-1,3-thiazol-4(5H)-one
—— 3-[(S)-4,5-dihydro-1H-imidazol-2-yl-(4-methylpiperazin-1-yl)methyl]phenol —— C15H22N4O
3-[(S)-4,5-dihydro-1H-imidazol-2-yl-(4-methylpiperazin-1-yl)methyl]phenol
—— 2-[2-[(3R)-3-(1,3-benzodioxol-5-yl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]-5-methoxyphenol —— C24H19N3O4S2
2-[2-[(3R)-3-(1,3-benzodioxol-5-yl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]-5-methoxyphenol
—— 2-[2-[(3R)-3-(4-fluorophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]-5-methoxyphenol —— C23H18FN3O2S2
2-[2-[(3R)-3-(4-fluorophenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-yl]-5-methoxyphenol
—— (5Z)-3-butyl-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C14H15NO4S
(5Z)-3-butyl-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— (5Z)-3-butyl-2-butylimino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C19H26N2O3S
(5Z)-3-butyl-2-butylimino-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (5Z)-3-tert-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H17NO3S2
(5Z)-3-tert-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid —— C17H19NO5S2
2-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanoic acid
—— (5Z)-3-(2,5-dimethylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO4S2
(5Z)-3-(2,5-dimethylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C15H17NO4S
(5Z)-3-butyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— (5Z)-3-(4-ethylphenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO3S2
(5Z)-3-(4-ethylphenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(2,4-dimethoxyphenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO5S2
(5Z)-3-(2,4-dimethoxyphenyl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-[2-(3,4-dimethoxyphenyl)ethyl]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C22H23NO6S2
(5Z)-3-[2-(3,4-dimethoxyphenyl)ethyl]-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(2-ethylphenyl)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5Z)-3-(2-ethylphenyl)-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(4-ethylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C20H19NO4S2
(5Z)-3-(4-ethylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-tert-butyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H19NO4S2
(5Z)-3-tert-butyl-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(4-butylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C22H23NO4S2
(5Z)-3-(4-butylphenyl)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H11NO4S2
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-(2-ethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-(2-ethylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(4-ethylphenyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5Z)-3-(4-ethylphenyl)-5-[(3-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-3-(2-ethylphenyl)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO2S2
(5Z)-3-(2-ethylphenyl)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-[2-(4-methoxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C19H17NO4S2
(5Z)-5-[(3,4-dihydroxyphenyl)methylidene]-3-[2-(4-methoxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one