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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
—— N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-N-(3-methylphenyl)butanediamide —— C19H21N3O4
N'-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-N-(3-methylphenyl)butanediamide
—— 4-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(4-fluorophenyl)pyrazolidine-3,5-dione —— C17H12ClFN2O4
4-[(5-Chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(4-fluorophenyl)pyrazolidine-3,5-dione
—— 3-[2-(3,4-Dihydroxyphenyl)ethylcarbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid —— C17H19NO5
3-[2-(3,4-Dihydroxyphenyl)ethylcarbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methyl-4-nitrobenzamide —— C16H15N3O5
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-3-methyl-4-nitrobenzamide
—— N-[[4-(diethylamino)phenyl]methylideneamino]-3,4,5-trihydroxybenzamide —— C18H21N3O4
N-[[4-(diethylamino)phenyl]methylideneamino]-3,4,5-trihydroxybenzamide
—— ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27BrN2O6S
ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[1-(4-methylphenyl)sulfonylindol-3-yl]prop-2-enamide —— C25H18N4O6S
2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[1-(4-methylphenyl)sulfonylindol-3-yl]prop-2-enamide
—— 4-[[4-(5-Phenyl-3,4-dihydropyrazol-2-yl)phenyl]methylideneamino]phenol —— C22H19N3O
4-[[4-(5-Phenyl-3,4-dihydropyrazol-2-yl)phenyl]methylideneamino]phenol
—— 3,4,5-trihydroxy-N-(1-phenylethylideneamino)benzamide —— C15H14N2O4
3,4,5-trihydroxy-N-(1-phenylethylideneamino)benzamide
—— N-[1-(4-ethylphenyl)ethylideneamino]-3,4,5-trihydroxybenzamide —— C17H18N2O4
N-[1-(4-ethylphenyl)ethylideneamino]-3,4,5-trihydroxybenzamide
—— 5-[(3-Chloro-4-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H11ClFNO3S
5-[(3-Chloro-4-hydroxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— 6-Ethenyl-5-(2-hydroxy-4,6-dimethoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C24H28O5
6-Ethenyl-5-(2-hydroxy-4,6-dimethoxyphenyl)-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— N-(1-cyclopropylethylideneamino)-3,4,5-trihydroxybenzamide —— C12H14N2O4
N-(1-cyclopropylethylideneamino)-3,4,5-trihydroxybenzamide
—— 3,4,5-trihydroxy-N-[(2,3,4-trimethoxyphenyl)methylideneamino]benzamide —— C17H18N2O7
3,4,5-trihydroxy-N-[(2,3,4-trimethoxyphenyl)methylideneamino]benzamide
—— 2-(2,4-Dihydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C16H22N2O3+2
2-(2,4-Dihydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylideneamino]-3-nitrobenzamide —— C15H12BrN3O5
N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylideneamino]-3-nitrobenzamide
—— 1-[(5R)-5-hydroxy-3-(2-methylpropyl)-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one —— C17H21F3N2O3
1-[(5R)-5-hydroxy-3-(2-methylpropyl)-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one
—— 1-[(5R)-3-cyclohexyl-5-hydroxy-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one —— C19H23F3N2O3
1-[(5R)-3-cyclohexyl-5-hydroxy-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one
—— 1-[(5S)-3-cyclohexyl-5-hydroxy-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one —— C19H23F3N2O3
1-[(5S)-3-cyclohexyl-5-hydroxy-5-(trifluoromethyl)-4H-pyrazol-1-yl]-3-(2-hydroxyphenyl)propan-1-one
—— (3R,7R)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-2H-[1,3]thiazolo[3,2-a]pyridine-8-carbonitrile —— C22H20N2O4S
(3R,7R)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-2H-[1,3]thiazolo[3,2-a]pyridine-8-carbonitrile
—— 6-Ethenyl-5-[2-hydroxy-5-(trifluoromethoxy)phenyl]-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione —— C23H23F3O4
6-Ethenyl-5-[2-hydroxy-5-(trifluoromethoxy)phenyl]-2,3,4a,8a-tetramethyl-5,8-dihydronaphthalene-1,4-dione
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(piperidin-1-ylmethyl)-1,3-thiazolidine-2,4-dione —— C17H20N2O4S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-3-(piperidin-1-ylmethyl)-1,3-thiazolidine-2,4-dione
—— (3S,7R)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-2H-[1,3]thiazolo[3,2-a]pyridine-8-carbonitrile —— C22H20N2O4S
(3S,7R)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-2H-[1,3]thiazolo[3,2-a]pyridine-8-carbonitrile
—— 2-(4-Ethylpiperazin-4-ium-1-yl)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H20N3O2S+
2-(4-Ethylpiperazin-4-ium-1-yl)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— 2-[4-(2-Hydroxyethyl)piperazin-4-ium-1-yl]-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H20N3O3S+
2-[4-(2-Hydroxyethyl)piperazin-4-ium-1-yl]-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-[2-[2-[(4-hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]-2-oxoethoxy]acetamide —— C20H22N4O7
N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-[2-[2-[(4-hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]-2-oxoethoxy]acetamide
—— (3S,7S)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-2H-[1,3]thiazolo[3,2-a]pyridine-8-carbonitrile —— C22H20N2O4S
(3S,7S)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-(4-methylphenyl)-5-oxo-6,7-dihydro-2H-[1,3]thiazolo[3,2-a]pyridine-8-carbonitrile
—— ethyl (4R)-6-[(4-fluoro-3-methylphenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C22H23FN2O7S
ethyl (4R)-6-[(4-fluoro-3-methylphenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (4R)-6-[(3-chloro-4-fluorophenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H20ClFN2O7S
ethyl (4R)-6-[(3-chloro-4-fluorophenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— ethyl (4S)-6-[(3-chloro-4-fluorophenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C21H20ClFN2O7S
ethyl (4S)-6-[(3-chloro-4-fluorophenyl)sulfonylmethyl]-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2,3,4a,8a-Tetrachloro-6-ethenyl-5-(2-hydroxy-4,6-dimethoxyphenyl)-5,8-dihydronaphthalene-1,4-dione —— C20H16Cl4O5
2,3,4a,8a-Tetrachloro-6-ethenyl-5-(2-hydroxy-4,6-dimethoxyphenyl)-5,8-dihydronaphthalene-1,4-dione
—— N-[1-(4-hydroxyphenyl)ethyl]-2-(thiophen-2-yl)acetamide —— C14H15NO2S
N-[1-(4-hydroxyphenyl)ethyl]-2-(thiophen-2-yl)acetamide
—— 7-ethenyl-8-(2-hydroxy-3-methylphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H22O3
7-ethenyl-8-(2-hydroxy-3-methylphenyl)-3,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 3,4,5-trihydroxy-N-[1-(4-nitrophenyl)ethylideneamino]benzamide —— C15H13N3O6
3,4,5-trihydroxy-N-[1-(4-nitrophenyl)ethylideneamino]benzamide
—— 3-(3,4-dihydroxyphenyl)-N-[(3-methoxy-4-propoxyphenyl)methylideneamino]propanamide —— C20H24N2O5
3-(3,4-dihydroxyphenyl)-N-[(3-methoxy-4-propoxyphenyl)methylideneamino]propanamide
—— Propan-2-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-sulfanylidene-1,3-diazinane-5-carboxylate —— C16H20N2O4S
Propan-2-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methylidene-2-sulfanylidene-1,3-diazinane-5-carboxylate
—— 7-ethenyl-8-(2-hydroxy-3-methylphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C22H24O3
7-ethenyl-8-(2-hydroxy-3-methylphenyl)-2,3,8a-trimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— 1-[3-Acetyl-4,6-dihydroxy-2-(4-hydroxyphenyl)-6-methylcyclohex-3-en-1-yl]ethanone —— C17H20O5
1-[3-Acetyl-4,6-dihydroxy-2-(4-hydroxyphenyl)-6-methylcyclohex-3-en-1-yl]ethanone
—— 3,4,5-trihydroxy-N-[1-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]ethylideneamino]benzamide —— C17H14F3N3O5
3,4,5-trihydroxy-N-[1-[3-[(2,2,2-trifluoroacetyl)amino]phenyl]ethylideneamino]benzamide
—— (8S)-3-(furan-2-ylmethyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C20H19N3O4S
(8S)-3-(furan-2-ylmethyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8R)-3-(furan-2-ylmethyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C20H19N3O4S
(8R)-3-(furan-2-ylmethyl)-8-(4-hydroxy-3-methoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— 2-[(4-Hydroxyphenyl)methylidene]-6-methylcyclohexan-1-one —— C14H16O2
2-[(4-Hydroxyphenyl)methylidene]-6-methylcyclohexan-1-one
—— 4-Hydroxy-3-nitrobenzenesulfonate —— C6H4NO6S-
4-Hydroxy-3-nitrobenzenesulfonate
—— 4-hydroxy-N-[2-[(4-hydroxy-3-nitrobenzoyl)hydrazinylidene]ethylideneamino]-3-nitrobenzamide —— C16H12N6O8
4-hydroxy-N-[2-[(4-hydroxy-3-nitrobenzoyl)hydrazinylidene]ethylideneamino]-3-nitrobenzamide
—— ethyl 5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl 5-(3,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-chloro-2-(N-hydroxy-C-pentylcarbonimidoyl)phenol —— C12H16ClNO2
4-chloro-2-(N-hydroxy-C-pentylcarbonimidoyl)phenol
—— 5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-ethoxyphenyl)imino-3-propyl-1,3-thiazolidin-4-one —— C22H23BrN2O4S
5-[(2-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-(4-ethoxyphenyl)imino-3-propyl-1,3-thiazolidin-4-one
—— methyl N-[1-(2,4-dihydroxyphenyl)ethenylamino]carbamate —— C10H12N2O4
methyl N-[1-(2,4-dihydroxyphenyl)ethenylamino]carbamate
—— 2-(2-Hydroxy-3-methoxyphenyl)ethanimidamide —— C9H12N2O2
2-(2-Hydroxy-3-methoxyphenyl)ethanimidamide
—— 4-Fluorbenzoesaeure-5-nitrosalicyliden-hydrazon 41377-08-6 C14H10FN3O4
4-Fluorbenzoesaeure-5-nitrosalicyliden-hydrazon