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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
—— 2-[Benzotriazol-1-yl-(3-hydroxyanilino)methyl]-4-nitrophenol —— C19H15N5O4
2-[Benzotriazol-1-yl-(3-hydroxyanilino)methyl]-4-nitrophenol
—— (4R)-4-butyl-4-(hydroxymethyl)-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione —— C20H22N2O4
(4R)-4-butyl-4-(hydroxymethyl)-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
—— 4-[(1S,3S)-1,3-dihydroxybutyl]-3-[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol —— C14H22O6
4-[(1S,3S)-1,3-dihydroxybutyl]-3-[(1S,3R)-1,3-dihydroxybutyl]benzene-1,2-diol
—— (5Z)-5-[(Z)-3-(furan-2-yl)prop-2-enylidene]-3-(4-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H11NO3S2
(5Z)-5-[(Z)-3-(furan-2-yl)prop-2-enylidene]-3-(4-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-[(5-Bromo-2-hydroxy-3-iodophenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one —— C22H26BrIN2O2S
5-[(5-Bromo-2-hydroxy-3-iodophenyl)methylidene]-3-cyclohexyl-2-cyclohexylimino-1,3-thiazolidin-4-one
—— (5E)-5-[(Z)-3-(furan-2-yl)prop-2-enylidene]-3-(4-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H11NO3S2
(5E)-5-[(Z)-3-(furan-2-yl)prop-2-enylidene]-3-(4-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]acetamide —— C18H16N2O4S3
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]acetamide
—— 2-chloro-6-(N-hydroxy-C-undecylcarbonimidoyl)phenol —— C18H28ClNO2
2-chloro-6-(N-hydroxy-C-undecylcarbonimidoyl)phenol
—— N-[2-(4-hydroxyphenyl)ethyl]-4-[(5E)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide —— C20H20N2O3S3
N-[2-(4-hydroxyphenyl)ethyl]-4-[(5E)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[(5E)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide —— C20H20N2O4S3
N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[(5E)-4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-[(4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-[(4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 3,4,5-trihydroxy-N-[(2-methyl-1-phenylpropylidene)amino]benzamide —— C17H18N2O4
3,4,5-trihydroxy-N-[(2-methyl-1-phenylpropylidene)amino]benzamide
—— N-[1-(2-hydroxyphenyl)ethylideneamino]-2-phenylcyclopropane-1-carboxamide —— C18H18N2O2
N-[1-(2-hydroxyphenyl)ethylideneamino]-2-phenylcyclopropane-1-carboxamide
—— (Z)-2-(4-bromophenyl)sulfonyl-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C16H12BrNO4S
(Z)-2-(4-bromophenyl)sulfonyl-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— methyl (4E)-1-cyclohexyl-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate —— C20H23NO4
methyl (4E)-1-cyclohexyl-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— (4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,2,5-thiadiazolidin-3-one —— C10H10N2O3S
(4E)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,2,5-thiadiazolidin-3-one
—— 2-[4-[(2R)-butan-2-yl]phenoxy]-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C20H24N2O4
2-[4-[(2R)-butan-2-yl]phenoxy]-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-2-imino-3-(1,3-thiazol-2-yl)-1,3-thiazolidin-4-one —— C13H9N3O2S2
(5E)-5-[(4-hydroxyphenyl)methylidene]-2-imino-3-(1,3-thiazol-2-yl)-1,3-thiazolidin-4-one
—— 5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one —— C18H16N2O3S
5-[(2-Hydroxy-3-methoxyphenyl)methylidene]-3-methyl-2-phenylimino-1,3-thiazolidin-4-one
—— (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-hydroxy-4-nitrophenyl)-2-phenylimidazol-4-one —— C23H17N3O6
(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(2-hydroxy-4-nitrophenyl)-2-phenylimidazol-4-one
—— 2-[4-[(2S)-butan-2-yl]phenoxy]-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C20H24N2O4
2-[4-[(2S)-butan-2-yl]phenoxy]-N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— (Z)-2-[4-(furan-2-yl)thiophen-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C18H13NO3S
(Z)-2-[4-(furan-2-yl)thiophen-2-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— 2-[(5E)-5-[(4-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O5S
2-[(5E)-5-[(4-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 3-[(5-tert-butyl-2-hydroxy-3-nitrophenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one —— C21H22N2O6
3-[(5-tert-butyl-2-hydroxy-3-nitrophenyl)methylidene]-5,6-dimethoxy-1H-indol-2-one
—— propan-2-yl 2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H20BrClN2O4S
propan-2-yl 2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2R)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide —— C19H18N2O5S2
(2R)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide
—— N-[[4-(diethylamino)phenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide —— C18H20N4O4
N-[[4-(diethylamino)phenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide
—— 2-[(5E)-5-[(3-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O4S2
2-[(5E)-5-[(3-chlorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 4-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide —— C21H22N2O5S2
4-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[(2S)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide
—— 4-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide —— C21H22N2O5S2
4-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylbutanamide
—— 2-[(5E)-5-[(3-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide —— C20H17ClN2O5S
2-[(5E)-5-[(3-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]acetamide
—— 3-[(5E)-5-[(2-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide —— C21H19ClN2O5S
3-[(5E)-5-[(2-chlorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-[(3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-[(3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 4-[(5E)-5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-(4-hydroxyphenyl)ethyl]butanamide —— C22H22N2O3S2
4-[(5E)-5-benzylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-N-[2-(4-hydroxyphenyl)ethyl]butanamide
—— (Z)-4-(1,3-benzothiazol-2-yl)-5-(3-hydroxy-4-methoxyphenyl)pent-4-enoic acid —— C19H17NO4S
(Z)-4-(1,3-benzothiazol-2-yl)-5-(3-hydroxy-4-methoxyphenyl)pent-4-enoic acid
—— 2-methoxy-5-[(Z)-2-(5-phenyl-1,3-benzoxazol-2-yl)ethenyl]phenol —— C22H17NO3
2-methoxy-5-[(Z)-2-(5-phenyl-1,3-benzoxazol-2-yl)ethenyl]phenol
—— 5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-(3-bromophenyl)imino-1,3-thiazolidin-4-one —— C16H9Br2N3O4S
5-[(3-Bromo-4-hydroxy-5-nitrophenyl)methylidene]-2-(3-bromophenyl)imino-1,3-thiazolidin-4-one
—— 2,6-Dimethoxy-4-[[[2-nitro-4-(trifluoromethyl)phenyl]hydrazinylidene]methyl]phenol —— C16H14F3N3O5
2,6-Dimethoxy-4-[[[2-nitro-4-(trifluoromethyl)phenyl]hydrazinylidene]methyl]phenol
—— (10Z)-10-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-phenyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one —— C23H18N2O3S
(10Z)-10-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-phenyl-6-thia-1,8-diazatricyclo[7.3.0.03,7]dodeca-3(7),4,8-trien-2-one
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-4-oxo-5-[(Z)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide —— C22H20N2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-4-oxo-5-[(Z)-3-phenylprop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide
—— (Z)-1-(4-hydroxy-3-methoxyphenyl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one —— C15H14O3S
(Z)-1-(4-hydroxy-3-methoxyphenyl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one
—— 3-Nitrophenyl-3-nitro-4-hydroxyphenylsulfon 38037-93-3 C12H8N2O7S
3-Nitrophenyl-3-nitro-4-hydroxyphenylsulfon
—— 3-(3-Hydroxy-4-methoxyphenyl)-2-(4-phenyl-1,3-thiazol-2-yl)prop-2-enenitrile —— C19H14N2O2S
3-(3-Hydroxy-4-methoxyphenyl)-2-(4-phenyl-1,3-thiazol-2-yl)prop-2-enenitrile
—— N-(2,4-difluorophenyl)-2-[5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H16F2N2O6S
N-(2,4-difluorophenyl)-2-[5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3,5-dimethylphenyl)imino-1,3-thiazolidin-4-one —— C19H17ClN2O3S
5-[(3-Chloro-4-hydroxy-5-methoxyphenyl)methylidene]-2-(3,5-dimethylphenyl)imino-1,3-thiazolidin-4-one
—— ZINC;[anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;hydroxide —— C15H17N3O3SZn+2
ZINC;[anilino(sulfoniumylidene)methyl]-[(3-methoxy-2-oxoniophenyl)methylideneamino]azanide;hydroxide
—— 2-Methoxy-4-{[(3-nitropyridin-4-yl)amino]methyl}phenol —— C13H13N3O4
2-Methoxy-4-{[(3-nitropyridin-4-yl)amino]methyl}phenol
—— 2-chloro-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-3-carboxamide —— C13H9ClN4O4
2-chloro-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-3-carboxamide
—— 2,6-Dichloro-4-(3,5-dichloro-4-hydroxy-2,6-dinitroanilino)-3,5-dinitrophenol —— C12H3Cl4N5O10
2,6-Dichloro-4-(3,5-dichloro-4-hydroxy-2,6-dinitroanilino)-3,5-dinitrophenol
—— 5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one —— C24H20N2O2S
5-[(4-Hydroxy-3,5-dimethylphenyl)methylidene]-3-phenyl-2-phenylimino-1,3-thiazolidin-4-one