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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
—— 4-chloro-5-nitro-2-[[(2Z)-2-(1,3,3-trimethylindol-2-ylidene)ethylidene]amino]phenol —— C19H18ClN3O3
4-chloro-5-nitro-2-[[(2Z)-2-(1,3,3-trimethylindol-2-ylidene)ethylidene]amino]phenol
—— (2S)-2-(2,3-dihydroxyphenyl)-3-(1,3,4-thiadiazol-2-yl)-1,3-thiazolidin-4-one —— C11H9N3O3S2
(2S)-2-(2,3-dihydroxyphenyl)-3-(1,3,4-thiadiazol-2-yl)-1,3-thiazolidin-4-one
—— (3Z)-2-amino-4-(3,5-dibromo-4-hydroxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile —— C13H6Br2N4O
(3Z)-2-amino-4-(3,5-dibromo-4-hydroxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile
—— (2S)-2-(4-hydroxyphenyl)propanenitrile —— C9H9NO
(2S)-2-(4-hydroxyphenyl)propanenitrile
—— 4-[(2R)-2-hydroxy-3-[2-(2-methylphenoxy)ethylamino]propoxy]-2,3,6-trimethylphenol —— C21H29NO4
4-[(2R)-2-hydroxy-3-[2-(2-methylphenoxy)ethylamino]propoxy]-2,3,6-trimethylphenol
—— 2-[(3R)-4-hydroxy-5,6,7,8-tetrahydro-3H-1,2,4-benzotriazin-3-yl]-6-methoxyphenol —— C14H17N3O3
2-[(3R)-4-hydroxy-5,6,7,8-tetrahydro-3H-1,2,4-benzotriazin-3-yl]-6-methoxyphenol
—— (1R,5S,6S)-5-ethyl-4-(4-hydroxyphenyl)-6-methylcyclohex-3-ene-1-carboxylic acid —— C16H20O3
(1R,5S,6S)-5-ethyl-4-(4-hydroxyphenyl)-6-methylcyclohex-3-ene-1-carboxylic acid
—— (3R,3aR)-3-(2-hydroxyphenyl)-2,3,3a,6-tetrahydropyrazolo[3,4-d][1,3]thiazol-5-one —— C10H9N3O2S
(3R,3aR)-3-(2-hydroxyphenyl)-2,3,3a,6-tetrahydropyrazolo[3,4-d][1,3]thiazol-5-one
—— (2Z)-2-{[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene}-1-benzothiophen-3(2H)-one —— C19H11NO5S
(2Z)-2-{[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene}-1-benzothiophen-3(2H)-one
—— (4S)-2-amino-4-(2-hydroxy-4-methoxyphenyl)-4,5-dihydro-1H-pyrimidin-6-one —— C11H13N3O3
(4S)-2-amino-4-(2-hydroxy-4-methoxyphenyl)-4,5-dihydro-1H-pyrimidin-6-one
—— 5-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-1,3-dimethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione —— C17H18N2O4S
5-[4-hydroxy-3-methoxy-5-(prop-2-en-1-yl)benzylidene]-1,3-dimethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
—— (5E)-5-(5-bromo-2-hydroxybenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione —— C16H10BrNO3S
(5E)-5-(5-bromo-2-hydroxybenzylidene)-3-phenyl-1,3-thiazolidine-2,4-dione
—— (E)-2-benzoyl-3-(4-hydroxy-2-methylanilino)prop-2-enenitrile —— C17H14N2O2
(E)-2-benzoyl-3-(4-hydroxy-2-methylanilino)prop-2-enenitrile
—— 4-[(Z)-2-(1-methylpyridin-1-ium-2-yl)ethenyl]benzene-1,2-diol —— C14H14NO2+
4-[(Z)-2-(1-methylpyridin-1-ium-2-yl)ethenyl]benzene-1,2-diol
—— N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2-(3-methylanilino)acetamide —— C16H16N4O4
N-[(Z)-(5-hydroxy-2-nitrophenyl)methylideneamino]-2-(3-methylanilino)acetamide
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-[(N-methylanilino)methyl]triazole-4-carboxamide —— C21H21N9O4
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-[(N-methylanilino)methyl]triazole-4-carboxamide
—— 2-[[bis[(2R)-2-hydroxypropyl]amino]methyl]-5-[[[(2R)-2-hydroxypropyl]-[(2S)-2-hydroxypropyl]amino]methyl]benzene-1,4-diol —— C20H36N2O6
2-[[bis[(2R)-2-hydroxypropyl]amino]methyl]-5-[[[(2R)-2-hydroxypropyl]-[(2S)-2-hydroxypropyl]amino]methyl]benzene-1,4-diol
—— 2-[(4R)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-6-nitrophenol —— C15H12N6O3
2-[(4R)-2-amino-1,4-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-4-yl]-6-nitrophenol
—— 2-[(2R,6S)-4-(4-chlorophenyl)-2-methyl-2-propyl-5,6-dihydro-1H-pyrimidin-6-yl]-6-methoxyphenol —— C21H25ClN2O2
2-[(2R,6S)-4-(4-chlorophenyl)-2-methyl-2-propyl-5,6-dihydro-1H-pyrimidin-6-yl]-6-methoxyphenol
—— 4-bromo-2-[(2S,6S)-4-(4-ethylphenyl)-2-propyl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C21H25BrN2O
4-bromo-2-[(2S,6S)-4-(4-ethylphenyl)-2-propyl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-chloro-2-[(2S,6S)-4-(4-ethylphenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C21H25ClN2O
4-chloro-2-[(2S,6S)-4-(4-ethylphenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6S)-4-(4-chlorophenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C19H20BrClN2O
4-bromo-2-[(2R,6S)-4-(4-chlorophenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-chloro-2-[(2R,6R)-4-(4-ethylphenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol —— C21H25ClN2O
4-chloro-2-[(2R,6R)-4-(4-ethylphenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]phenol
—— 4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-methyl-2-propyl-5,6-dihydro-1H-pyrimidin-6-yl]phenol —— C22H27BrN2O
4-bromo-2-[(2R,6R)-4-(4-ethylphenyl)-2-methyl-2-propyl-5,6-dihydro-1H-pyrimidin-6-yl]phenol
—— 2-[(2S,6S)-4-(4-chlorophenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C20H23ClN2O2
2-[(2S,6S)-4-(4-chlorophenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 2-[(2R,6S)-4-(4-chlorophenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol —— C20H23ClN2O2
2-[(2R,6S)-4-(4-chlorophenyl)-2-propan-2-yl-1,2,5,6-tetrahydropyrimidin-6-yl]-6-methoxyphenol
—— 5-[(2-Hydroxy-3,5-dinitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C11H6N4O7S
5-[(2-Hydroxy-3,5-dinitrophenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27BrN2O6S
ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O3S2
(5Z)-5-[(2-hydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (2Z)-5-(4-bromophenyl)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z)-5-(4-bromophenyl)-2-[(5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-[(E)-2-(1-benzyl-3,3-dimethylindol-1-ium-2-yl)ethenyl]-4,6-dinitrophenol —— C25H22N3O5+
2-[(E)-2-(1-benzyl-3,3-dimethylindol-1-ium-2-yl)ethenyl]-4,6-dinitrophenol
—— (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[4-[(5E)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-yl]-1,3-thiazol-4-one —— C24H20N4O4S2
(5Z)-5-[(2-hydroxyphenyl)methylidene]-2-[4-[(5E)-5-[(2-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]piperazin-1-yl]-1,3-thiazol-4-one
—— (Z)-3-(1,1-dioxidotetrahydrothiophen-3-yl)-5-(3-hydroxybenzylidene)-2-thioxothiazolidin-4-one —— C14H13NO4S3
(Z)-3-(1,1-dioxidotetrahydrothiophen-3-yl)-5-(3-hydroxybenzylidene)-2-thioxothiazolidin-4-one
—— (5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-(3-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H11BrN2O4S2
(5E)-5-[(3-bromo-4-hydroxy-5-nitrophenyl)methylidene]-3-(3-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(thiophen-2-yl)-N'-[(Z)-(2,4,6-tribromo-3-hydroxyphenyl)methylidene]acetohydrazide —— C13H9Br3N2O2S
2-(thiophen-2-yl)-N'-[(Z)-(2,4,6-tribromo-3-hydroxyphenyl)methylidene]acetohydrazide
—— 5-[(E)-1-(5-Bromo-2-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolan-4-one —— C19H17BrN2O3S
5-[(E)-1-(5-Bromo-2-hydroxyphenyl)methylidene]-3-(2-methoxyethyl)-2-(phenylimino)-1,3-thiazolan-4-one
—— ethyl (2Z,7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-[(3-nitrophenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21N3O7S
ethyl (2Z,7R)-7-(4-hydroxy-3-methoxyphenyl)-5-methyl-2-[(3-nitrophenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-chloro-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-4-hydroxy-2-methoxybenzamide —— C15H21ClN2O3
5-chloro-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-4-hydroxy-2-methoxybenzamide
—— 2-methoxy-5-[(Z)-[(2,4,6-trichlorophenyl)hydrazinylidene]methyl]phenol —— C14H11Cl3N2O2
2-methoxy-5-[(Z)-[(2,4,6-trichlorophenyl)hydrazinylidene]methyl]phenol
—— 5-chloro-N-[[(2R)-1-ethyl-1-methylpyrrolidin-1-ium-2-yl]methyl]-4-hydroxy-2-methoxybenzamide —— C16H24ClN2O3+
5-chloro-N-[[(2R)-1-ethyl-1-methylpyrrolidin-1-ium-2-yl]methyl]-4-hydroxy-2-methoxybenzamide
—— (S)-cyano-(4-hydroxy-3-methoxyphenyl)methanesulfonic acid —— C9H9NO5S
(S)-cyano-(4-hydroxy-3-methoxyphenyl)methanesulfonic acid
—— 4-nitro-2-[(4S)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-4-yl]phenol —— C12H12N4O3
4-nitro-2-[(4S)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-4-yl]phenol
—— (E)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-methyl-2-nitrophenyl)furan-2-yl]prop-2-enamide —— C21H14N4O7
(E)-2-cyano-N-(2-hydroxy-4-nitrophenyl)-3-[5-(4-methyl-2-nitrophenyl)furan-2-yl]prop-2-enamide
—— (2S,4R)-2-(2-hydroxy-5-nitrophenyl)-1,3-thiazolidine-4-carboxylic acid —— C10H10N2O5S
(2S,4R)-2-(2-hydroxy-5-nitrophenyl)-1,3-thiazolidine-4-carboxylic acid
—— (2-Hydroxyphenyl)methyl-[2-[(2-hydroxyphenyl)methylazanidyl]phenyl]azanide;iron(2+) —— C20H18FeN2O2
(2-Hydroxyphenyl)methyl-[2-[(2-hydroxyphenyl)methylazanidyl]phenyl]azanide;iron(2+)
—— (2R)-2-(4-hydroxyphenyl)-2-sulfoacetic acid —— C8H8O6S
(2R)-2-(4-hydroxyphenyl)-2-sulfoacetic acid
—— (2R)-2-(3-bromophenyl)-3-(5-chloro-2-hydroxyphenyl)-1,3-thiazolidin-4-one —— C15H11BrClNO2S
(2R)-2-(3-bromophenyl)-3-(5-chloro-2-hydroxyphenyl)-1,3-thiazolidin-4-one
—— methyl (2Z,5S)-2-[[4-(2-amino-2-oxoethoxy)-3-methoxyphenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H24ClN3O8S
methyl (2Z,5S)-2-[[4-(2-amino-2-oxoethoxy)-3-methoxyphenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-2-[(1-ethylpyrazol-3-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H22N4O4S
ethyl (2Z,5R)-2-[(1-ethylpyrazol-3-yl)methylidene]-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E,5S)-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-2-[(1,3,5-trimethylpyrazol-4-yl)methylidene]-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C28H27N5O4S
(2E,5S)-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-2-[(1,3,5-trimethylpyrazol-4-yl)methylidene]-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide