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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
—— 1-[(1R)-1-(2-hydroxyphenyl)ethyl]-1-methyl-3-[(1S)-1-phenylethyl]thiourea —— C18H22N2OS
1-[(1R)-1-(2-hydroxyphenyl)ethyl]-1-methyl-3-[(1S)-1-phenylethyl]thiourea
—— (5Z)-2-(4-ethylpiperazin-4-ium-1-yl)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H20N3O2S+
(5Z)-2-(4-ethylpiperazin-4-ium-1-yl)-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (5Z)-2-(4-acetylpiperazin-1-yl)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H17N3O3S
(5Z)-2-(4-acetylpiperazin-1-yl)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— (Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile —— C17H15NO4S
(Z)-3-(4-hydroxy-3-methoxyphenyl)-2-(4-methylphenyl)sulfonylprop-2-enenitrile
—— 3-{(Z)-[2-(4-ethylpiperazin-1-ium-1-yl)-4-oxo-1,3-thiazol-5(4H)-ylidene]methyl}phenolate —— C16H19N3O2S
3-{(Z)-[2-(4-ethylpiperazin-1-ium-1-yl)-4-oxo-1,3-thiazol-5(4H)-ylidene]methyl}phenolate
—— ethyl (4S,5R,6S)-4-hydroxy-6-(2-hydroxy-5-nitrophenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate —— C14H14F3N3O6S
ethyl (4S,5R,6S)-4-hydroxy-6-(2-hydroxy-5-nitrophenyl)-2-sulfanylidene-4-(trifluoromethyl)-1,3-diazinane-5-carboxylate
—— (5E)-3-(4-hydroxyphenyl)-5-(pyridin-4-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H10N2O2S2
(5E)-3-(4-hydroxyphenyl)-5-(pyridin-4-ylmethylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate —— C14H11BrNO5S2-
3-[(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoate
—— (Z)-3-(4-hydroxyphenyl)-5-(pyridin-4-ylmethylene)-2-thioxothiazolidin-4-one —— C15H10N2O2S2
(Z)-3-(4-hydroxyphenyl)-5-(pyridin-4-ylmethylene)-2-thioxothiazolidin-4-one
—— N-[(5E)-5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-4-hydroxy-3-methoxybenzamide —— C20H18N2O6S2
N-[(5E)-5-[(3,4-dimethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-4-hydroxy-3-methoxybenzamide
—— Diethyl-[(2-hydroxy-5-methoxyphenyl)methyl]azanium —— C12H20NO2+
Diethyl-[(2-hydroxy-5-methoxyphenyl)methyl]azanium
—— (4Z)-4-[(2-hydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one —— C11H9NO3
(4Z)-4-[(2-hydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one
—— 1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[3-[(2S)-2-methylpiperidin-1-yl]propyl]urea —— C20H33N3O2
1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[3-[(2S)-2-methylpiperidin-1-yl]propyl]urea
—— 1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[3-[(2R)-2-methylpiperidin-1-yl]propyl]urea —— C20H33N3O2
1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[3-[(2R)-2-methylpiperidin-1-yl]propyl]urea
—— N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,5-dimethylfuran-3-carboxamide —— C15H16N2O4
N-[(3-hydroxy-4-methoxyphenyl)methylideneamino]-2,5-dimethylfuran-3-carboxamide
—— 3,5-Diethyl 1-[(4-fluorophenyl)methyl]-4-(3-hydroxy-4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C25H26FNO6
3,5-Diethyl 1-[(4-fluorophenyl)methyl]-4-(3-hydroxy-4-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— methyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-methyl-5-oxo-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate —— C22H18BrNO5
methyl (4R)-4-(3-bromo-4-hydroxy-5-methoxyphenyl)-2-methyl-5-oxo-1,4-dihydroindeno[1,2-b]pyridine-3-carboxylate
—— (17E)-tricyclo[20.2.2.02,7]hexacosa-1(24),2(7),3,5,17,22,25-heptaene-3,5,24,25-tetrol —— C26H34O4
(17E)-tricyclo[20.2.2.02,7]hexacosa-1(24),2(7),3,5,17,22,25-heptaene-3,5,24,25-tetrol
—— N-[(Z)-1-(3,5-dihydroxyphenyl)ethylideneamino]-2-(3-methylphenoxy)acetamide —— C17H18N2O4
N-[(Z)-1-(3,5-dihydroxyphenyl)ethylideneamino]-2-(3-methylphenoxy)acetamide
—— (2Z,5E)-2-((3,5-dichlorophenyl)imino)-5-(4-hydroxy-3-methoxybenzylidene)thiazolidin-4-one —— C17H12Cl2N2O3S
(2Z,5E)-2-((3,5-dichlorophenyl)imino)-5-(4-hydroxy-3-methoxybenzylidene)thiazolidin-4-one
—— 2-[(Z)-3,5-Dichloro-phenylimino]-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-4-one 18101-21-8 C17H12Cl2N2O3S
2-[(Z)-3,5-Dichloro-phenylimino]-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-4-one
—— 4-methoxy-2-[2-[(2Z)-2-(1-pyridin-4-ylethylidene)hydrazinyl]-1,3-thiazol-4-yl]phenol —— C17H16N4O2S
4-methoxy-2-[2-[(2Z)-2-(1-pyridin-4-ylethylidene)hydrazinyl]-1,3-thiazol-4-yl]phenol
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(1H-indol-3-yl)acetamide —— C18H17N3O3
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-(1H-indol-3-yl)acetamide
—— 5-methoxy-2-[2-[(2Z)-2-[(5R)-3,3,5-trimethylcyclohexylidene]hydrazinyl]-1,3-thiazol-4-yl]phenol —— C19H25N3O2S
5-methoxy-2-[2-[(2Z)-2-[(5R)-3,3,5-trimethylcyclohexylidene]hydrazinyl]-1,3-thiazol-4-yl]phenol
—— N,N'-[(4,5-Dihydroxy-1,2-phenylene)bis(methylene)]bis(2-chloroacetamide) —— C12H14Cl2N2O4
N,N'-[(4,5-Dihydroxy-1,2-phenylene)bis(methylene)]bis(2-chloroacetamide)
—— 4-methoxy-2-[2-[(2Z)-2-(1-pyridin-3-ylethylidene)hydrazinyl]-1,3-thiazol-4-yl]phenol —— C17H16N4O2S
4-methoxy-2-[2-[(2Z)-2-(1-pyridin-3-ylethylidene)hydrazinyl]-1,3-thiazol-4-yl]phenol
—— 2-(2,4-dibromo-6-methoxyphenoxy)-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide —— C16H13Br2N3O6
2-(2,4-dibromo-6-methoxyphenoxy)-N-[(5-hydroxy-2-nitrophenyl)methylideneamino]acetamide
—— (7S)-5-amino-4-(4-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,1-dioxo-3,7-dihydro-2H-thieno[3,2-b]pyridine-6-carbonitrile —— C21H18FN3O4S
(7S)-5-amino-4-(4-fluorophenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,1-dioxo-3,7-dihydro-2H-thieno[3,2-b]pyridine-6-carbonitrile
—— (5R)-1-benzyl-5-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinane-2,4,6-trione —— C19H18N2O5
(5R)-1-benzyl-5-[(4-hydroxy-3-methoxyphenyl)methyl]-1,3-diazinane-2,4,6-trione
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide —— C20H20N2O4S3
N-[2-(3,4-dihydroxyphenyl)ethyl]-4-[4-oxo-2-sulfanylidene-5-(thiophen-2-ylmethylidene)-1,3-thiazolidin-3-yl]butanamide
—— 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-N-[(2-hydroxy-5-nitrophenyl)methylideneamino]heptanamide —— C14H6F13N3O4
2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-N-[(2-hydroxy-5-nitrophenyl)methylideneamino]heptanamide
—— (1S,5R)-N-[(4-hydroxyphenyl)methyl]-9-oxobicyclo[3.3.1]nonane-3-carboxamide —— C17H21NO3
(1S,5R)-N-[(4-hydroxyphenyl)methyl]-9-oxobicyclo[3.3.1]nonane-3-carboxamide
—— 1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(1S)-1-(5-methylfuran-2-yl)ethyl]urea —— C16H20N2O3
1-[(2-hydroxyphenyl)methyl]-1-methyl-3-[(1S)-1-(5-methylfuran-2-yl)ethyl]urea
—— 1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[(1S)-1-(5-methylfuran-2-yl)ethyl]urea —— C18H24N2O3
1-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]-3-[(1S)-1-(5-methylfuran-2-yl)ethyl]urea
—— N-(2-hydroxy-5-nitrophenyl)-6-[5-[(4-methylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide —— C23H23N3O5S2
N-(2-hydroxy-5-nitrophenyl)-6-[5-[(4-methylphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]hexanamide
—— 1-(3,4-Dimethylphenyl)-4-[(2-hydroxy-3-methylphenyl)methylidene]pyrazolidine-3,5-dione —— C19H18N2O3
1-(3,4-Dimethylphenyl)-4-[(2-hydroxy-3-methylphenyl)methylidene]pyrazolidine-3,5-dione
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[3-(furan-2-yl)prop-2-enylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H18N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[5-[3-(furan-2-yl)prop-2-enylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— ethyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-5-(3-methoxy-4-propan-2-yloxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H32N2O6S
ethyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-5-(3-methoxy-4-propan-2-yloxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N,N'-bis[(3-hydroxyphenyl)methylideneamino]decanediamide —— C24H30N4O4
N,N'-bis[(3-hydroxyphenyl)methylideneamino]decanediamide
—— 2-[5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-3-thiazolidinyl]-2-phenylacetic acid —— C19H15NO5S2
2-[5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-3-thiazolidinyl]-2-phenylacetic acid
—— 2-(4-hydroxy-3-nitrophenyl)-N-[2-(3-methoxy-3-methylbutyl)sulfanyl-1,3-benzothiazol-6-yl]acetamide —— C21H23N3O5S2
2-(4-hydroxy-3-nitrophenyl)-N-[2-(3-methoxy-3-methylbutyl)sulfanyl-1,3-benzothiazol-6-yl]acetamide
—— N-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylideneamino]-2-hydroxy-2-phenylacetamide —— C16H15ClN2O4
N-[(3-chloro-4-hydroxy-5-methoxyphenyl)methylideneamino]-2-hydroxy-2-phenylacetamide
—— (2S)-2-(3-chloro-4-hydroxyphenyl)-2-(methylamino)acetonitrile —— C9H9ClN2O
(2S)-2-(3-chloro-4-hydroxyphenyl)-2-(methylamino)acetonitrile
—— (2R)-2-(3-chloro-4-hydroxyphenyl)-2-(methylamino)acetonitrile —— C9H9ClN2O
(2R)-2-(3-chloro-4-hydroxyphenyl)-2-(methylamino)acetonitrile
—— 2-chloro-4-[(1R)-2-hydroxy-1-(methylamino)ethyl]phenol —— C9H12ClNO2
2-chloro-4-[(1R)-2-hydroxy-1-(methylamino)ethyl]phenol
—— (2S)-2-(3-chloro-4-hydroxyphenyl)-2-(diethylamino)acetonitrile —— C12H15ClN2O
(2S)-2-(3-chloro-4-hydroxyphenyl)-2-(diethylamino)acetonitrile
—— (2R)-2-(3-chloro-4-hydroxyphenyl)-2-(diethylamino)acetonitrile —— C12H15ClN2O
(2R)-2-(3-chloro-4-hydroxyphenyl)-2-(diethylamino)acetonitrile
—— 2-chloro-4-[(1S)-2-hydroxy-1-(methylamino)ethyl]phenol —— C9H12ClNO2
2-chloro-4-[(1S)-2-hydroxy-1-(methylamino)ethyl]phenol
—— (2S)-2-(3-chloro-4-hydroxyphenyl)-2-(propan-2-ylamino)acetonitrile —— C11H13ClN2O
(2S)-2-(3-chloro-4-hydroxyphenyl)-2-(propan-2-ylamino)acetonitrile
—— (2S)-2-(3-chloro-4-hydroxyphenyl)-2-(cyclopropylamino)acetonitrile —— C11H11ClN2O
(2S)-2-(3-chloro-4-hydroxyphenyl)-2-(cyclopropylamino)acetonitrile