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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
—— 6-Cyclopentyl-3-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-[2-(5-ethyl-2-hydroxy-4-methoxyphenyl)ethyl]oxane-2,4-dione —— C29H36N4O5
6-Cyclopentyl-3-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-[2-(5-ethyl-2-hydroxy-4-methoxyphenyl)ethyl]oxane-2,4-dione
—— 3-Methyl-4-(2,4,5-trihydroxy-3-methylphenyl)butan-2-one —— C12H16O4
3-Methyl-4-(2,4,5-trihydroxy-3-methylphenyl)butan-2-one
—— N'-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-N-(4-chloro-2-methylphenyl)butanediamide —— C19H19BrClN3O4
N'-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-N-(4-chloro-2-methylphenyl)butanediamide
—— Ethyl 2-(4-hydroxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)propanoate —— C13H16O3
Ethyl 2-(4-hydroxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)propanoate
—— N-[(Z)-(5-bromo-2,4-dimethoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C16H14BrN3O6
N-[(Z)-(5-bromo-2,4-dimethoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— 4-(2-Diethoxyphosphoryl-2-pyrazin-2-yliminoethyl)-2,6-dimethoxyphenol —— C18H24N3O6P
4-(2-Diethoxyphosphoryl-2-pyrazin-2-yliminoethyl)-2,6-dimethoxyphenol
—— ethyl (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylanilino)-4-oxothiophene-3-carboxylate —— C22H21NO5S
ethyl (5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylanilino)-4-oxothiophene-3-carboxylate
—— (4-Hydroxy-3,5-dimethylphenyl) 3,3-dimethylbutaneperoxoate —— C14H20O4
(4-Hydroxy-3,5-dimethylphenyl) 3,3-dimethylbutaneperoxoate
—— 2-Methoxy-4-[1-[methoxy(methyl)phosphoryl]oxy-2-(6-methylpyridin-3-yl)ethyl]-6-methylphenol —— C18H24NO5P
2-Methoxy-4-[1-[methoxy(methyl)phosphoryl]oxy-2-(6-methylpyridin-3-yl)ethyl]-6-methylphenol
—— (5Z)-3-benzyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C18H15NO4S
(5Z)-3-benzyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 5-Hexoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)pentan-2-one —— C18H28O5
5-Hexoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)pentan-2-one
—— 2,3,4-Trinitrosophenol —— C6H3N3O4
2,3,4-Trinitrosophenol
—— 1-[2-Hydroxy-5-(2-hydroxyethyl)phenyl]-3-methylbut-2-en-1-one —— C13H16O3
1-[2-Hydroxy-5-(2-hydroxyethyl)phenyl]-3-methylbut-2-en-1-one
—— N'-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-N-(4-methoxyphenyl)butanediamide —— C19H20BrN3O5
N'-[(Z)-(3-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-N-(4-methoxyphenyl)butanediamide
—— 1,3-Diethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C16H18N2O4S
1,3-Diethyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-[3-[1-(3-hydroxy-2-methoxyphenyl)ethylamino]cyclopentyl]-N-piperidin-4-ylbenzamide —— C26H35N3O3
4-[3-[1-(3-hydroxy-2-methoxyphenyl)ethylamino]cyclopentyl]-N-piperidin-4-ylbenzamide
—— (6E)-2,4-dibromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H8Br2N2O4
(6E)-2,4-dibromo-6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 1-(2,3-dimethylphenyl)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea —— C17H19N3O2S
1-(2,3-dimethylphenyl)-3-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea
—— 3,4,5-trihydroxy-N-[(Z)-(2-methoxy-5-methylsulfanylthiophen-3-yl)methylideneamino]benzamide —— C14H14N2O5S2
3,4,5-trihydroxy-N-[(Z)-(2-methoxy-5-methylsulfanylthiophen-3-yl)methylideneamino]benzamide
—— 4-[3-(Furan-2-ylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]phenol —— C20H19NO3
4-[3-(Furan-2-ylmethyl)-4-phenyl-1,3-oxazolidin-2-yl]phenol
—— Methyl 2-[3-(difluoromethyl)-4-hydroxyphenyl]acetate —— C10H10F2O3
Methyl 2-[3-(difluoromethyl)-4-hydroxyphenyl]acetate
—— 2-methoxy-5-[(Z)-(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylhydrazinylidene)methyl]phenol —— C18H18N4O2S
2-methoxy-5-[(Z)-(5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-ylhydrazinylidene)methyl]phenol
—— (6Z)-6-[5-(4-hydroxy-3-methoxyphenyl)pyrazolidin-3-ylidene]cyclohexa-2,4-dien-1-one —— C16H16N2O3
(6Z)-6-[5-(4-hydroxy-3-methoxyphenyl)pyrazolidin-3-ylidene]cyclohexa-2,4-dien-1-one
—— 3-[1-[1-[Bis(trihydroxymethyl)amino]-1-hydroxy-3-methylbutyl]cyclobutyl]-6-chlorobenzene-1,2,4,5-tetrol —— C17H26ClNO11
3-[1-[1-[Bis(trihydroxymethyl)amino]-1-hydroxy-3-methylbutyl]cyclobutyl]-6-chlorobenzene-1,2,4,5-tetrol
—— Fluoromethane;3-fluoro-2-methylphenol —— C8H10F2O
Fluoromethane;3-fluoro-2-methylphenol
—— 4-[2-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-yliminoethyl]-2,6-dimethoxyphenol —— C21H29N2O6P
4-[2-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-yliminoethyl]-2,6-dimethoxyphenol
—— (5Z)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C10H5BrClNO3S
(5Z)-5-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 5-[(3-Fluoro-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C15H13FN2O4S
5-[(3-Fluoro-4-hydroxy-5-methoxyphenyl)methylidene]-1-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— 4-[1-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-yliminoethyl]-2-methoxy-6-methylphenol —— C21H29N2O5P
4-[1-Di(propan-2-yloxy)phosphoryl-2-pyridin-3-yliminoethyl]-2-methoxy-6-methylphenol
—— 1-Amino-2-(2-amino-3,4,6-trihydroxyphenyl)ethane-1,1,2,2-tetrol —— C8H12N2O7
1-Amino-2-(2-amino-3,4,6-trihydroxyphenyl)ethane-1,1,2,2-tetrol
—— N-[(Z)-(3-bromo-4-phenylmethoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide —— C21H16BrN3O5
N-[(Z)-(3-bromo-4-phenylmethoxyphenyl)methylideneamino]-2-hydroxy-5-nitrobenzamide
—— (5Z)-5-[(2,3-dihydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H11NO4S2
(5Z)-5-[(2,3-dihydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-Bromophenol;ethane —— C8H11BrO
2-Bromophenol;ethane
—— methyl (2E)-5-amino-6-cyano-7-(4-hydroxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate —— C25H21N3O7S
methyl (2E)-5-amino-6-cyano-7-(4-hydroxy-3-methoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-oxo-7H-[1,3]thiazolo[3,2-a]pyridine-8-carboxylate
—— (5Z)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione —— C10H6N2O5S
(5Z)-5-[(2-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— (5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one —— C10H8N2O3S
(5Z)-5-[(2,4-dihydroxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one
—— 3-[(5Z)-5-[(3-hydroxy-2-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C14H13NO5S2
3-[(5Z)-5-[(3-hydroxy-2-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— ethyl (2Z)-2-(5-bromo-2-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19BrN2O4S
ethyl (2Z)-2-(5-bromo-2-hydroxybenzylidene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-bromobut-2-ene;N-[2-(3-hydroxyphenyl)ethyl]-N-methylacetamide —— C15H22BrNO2
1-bromobut-2-ene;N-[2-(3-hydroxyphenyl)ethyl]-N-methylacetamide
—— 4-[4-(3,4-Dimethoxyphenyl)buta-1,3-dienyl]-2-methoxyphenol —— C19H20O4
4-[4-(3,4-Dimethoxyphenyl)buta-1,3-dienyl]-2-methoxyphenol
—— 2-(2-Chloro-6-methylpyridin-3-yl)-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enenitrile —— C15H10ClN3O4
2-(2-Chloro-6-methylpyridin-3-yl)-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enenitrile
—— (2-Hydroxyphenyl)methoxy-methyl-oxophosphanium —— C8H10O3P+
(2-Hydroxyphenyl)methoxy-methyl-oxophosphanium
—— N-[6-[3-(2-hydroxyphenyl)propanoylamino]hexyl]-1-propan-2-ylideneoxoniomethanimidate —— C19H28N2O4
N-[6-[3-(2-hydroxyphenyl)propanoylamino]hexyl]-1-propan-2-ylideneoxoniomethanimidate
—— Ethyl (2Z)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-[2-(propan-2-yloxy)phenyl]-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C27H27BrN2O6S
Ethyl (2Z)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-[2-(propan-2-yloxy)phenyl]-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one —— C18H11BrF3NO3S2
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-sulfanylidene-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one
—— 2-(3-hydroxy-4-methoxyphenyl)-N-[2-(3-hydroxy-4-methoxyphenyl)ethynylsulfinyl]ethanesulfinamide —— C18H19NO6S2
2-(3-hydroxy-4-methoxyphenyl)-N-[2-(3-hydroxy-4-methoxyphenyl)ethynylsulfinyl]ethanesulfinamide
—— 4-Amino-3-nitrophenol;ethane —— C8H12N2O3
4-Amino-3-nitrophenol;ethane
—— 2-hydroxy-N-[(Z)-(5-methylfuran-2-yl)methylideneamino]-5-nitrobenzamide —— C13H11N3O5
2-hydroxy-N-[(Z)-(5-methylfuran-2-yl)methylideneamino]-5-nitrobenzamide
—— N-[(Z)-[3-bromo-4-[(2-chlorophenyl)methoxy]-5-methoxyphenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide —— C22H17BrClN3O6
N-[(Z)-[3-bromo-4-[(2-chlorophenyl)methoxy]-5-methoxyphenyl]methylideneamino]-2-hydroxy-5-nitrobenzamide
—— 2,4,5,6-Tetrakis(prop-2-ynyl)benzene-1,3-diol —— C18H14O2
2,4,5,6-Tetrakis(prop-2-ynyl)benzene-1,3-diol