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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
—— 5-(1-adamantyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-pyrazole-3-carboxamide —— C22H26N4O3
5-(1-adamantyl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-1H-pyrazole-3-carboxamide
—— 5-[(Z)-[(1-benzylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C20H18N6O2
5-[(Z)-[(1-benzylpyrazolo[3,4-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— (2Z,5Z)-5-benzylidene-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one —— C23H17N3O2S
(2Z,5Z)-5-benzylidene-2-[(Z)-benzylidenehydrazinylidene]-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one
—— 2-[[4-Methoxy-3-(2-morpholin-4-ylethoxy)phenyl]methoxy]-5-methylphenol —— C21H27NO5
2-[[4-Methoxy-3-(2-morpholin-4-ylethoxy)phenyl]methoxy]-5-methylphenol
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-oxo-1H-pyridazine-3-carboxamide —— C13H12N4O4
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-6-oxo-1H-pyridazine-3-carboxamide
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-imino-1-methylimidazolidin-4-one —— C12H12BrN3O3
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-2-imino-1-methylimidazolidin-4-one
—— 4-Fluoro-5,6-dimethylbenzene-1,2,3-triol —— C8H9FO3
4-Fluoro-5,6-dimethylbenzene-1,2,3-triol
—— 4-[(E)-2-(2,2-dimethyl-6-phenyl-1,3-dioxin-1-ium-4-yl)ethenyl]benzene-1,2-diol —— C20H19O4+
4-[(E)-2-(2,2-dimethyl-6-phenyl-1,3-dioxin-1-ium-4-yl)ethenyl]benzene-1,2-diol
—— 4-[(E)-2-(3,4-Dihydroxy-phenyl)-vinyl]-2,2-dimethyl-6-phenyl-2H-[1,3]dioxin-1-ylium; perchlorate —— C20H19O4*ClO4
4-[(E)-2-(3,4-Dihydroxy-phenyl)-vinyl]-2,2-dimethyl-6-phenyl-2H-[1,3]dioxin-1-ylium; perchlorate
—— ethyl (2Z)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18BrClN2O4S
ethyl (2Z)-2-[(5-bromo-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H8BrN3O6S2
(5Z)-5-[(3-bromo-2-hydroxy-5-nitrophenyl)methylidene]-3-(4-nitrophenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— (E)-but-2-enedioate;[3-[(dimethylazaniumyl)methyl]-2-hydroxy-5-methoxyphenyl]methyl-dimethylazanium —— C17H26N2O6
(E)-but-2-enedioate;[3-[(dimethylazaniumyl)methyl]-2-hydroxy-5-methoxyphenyl]methyl-dimethylazanium
—— Ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C24H20BrClN2O5S
Ethyl (2Z)-2-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-5-(4-chlorophenyl)-7-methyl-3-oxo-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— ethyl (2Z)-5-(1,3-benzodioxol-5-yl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22N2O7S
ethyl (2Z)-5-(1,3-benzodioxol-5-yl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-Amino-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylene]-3-oxo-4,7-dihydro-1,3-thiazolidino[3,2-a]pyridine-6,8-dicarbonitrile —— C22H14N4O3S
5-Amino-7-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methylene]-3-oxo-4,7-dihydro-1,3-thiazolidino[3,2-a]pyridine-6,8-dicarbonitrile
—— (5Z)-3-cyclohexyl-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H17NO2S2
(5Z)-3-cyclohexyl-5-[(4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— decyl N-hydroxycarbamate;1-hydroxy-1-methyl-3,3-dioctylurea;N-hydroxy-N-methylhexadecanamide;2-sulfanylethyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate —— C59H114N4O10S
decyl N-hydroxycarbamate;1-hydroxy-1-methyl-3,3-dioctylurea;N-hydroxy-N-methylhexadecanamide;2-sulfanylethyl 3-(4-hydroxy-3,5-dimethylphenyl)propanoate
—— ethyl (2Z)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C24H21ClN2O5S
ethyl (2Z)-5-(2-chlorophenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— Ethyl (2Z)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate —— C23H20N2O4S
Ethyl (2Z)-2-[(3-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-2H,3H,5H-[1,3]thiazolo[3,2-A]pyrimidine-6-carboxylate
—— 2-[4-[2,5-dihydroxy-4-(2-oxoethylamino)anilino]anilino]-N,N-diethylethanamine oxide —— C20H28N4O4
2-[4-[2,5-dihydroxy-4-(2-oxoethylamino)anilino]anilino]-N,N-diethylethanamine oxide
—— 2-[[4-[(2Z)-2-[(3-chloro-4-methylphenyl)methylidene]hydrazinyl]-6-(diethylamino)-1,3,5-triazin-2-yl]amino]-4-nitrophenol —— C21H23ClN8O3
2-[[4-[(2Z)-2-[(3-chloro-4-methylphenyl)methylidene]hydrazinyl]-6-(diethylamino)-1,3,5-triazin-2-yl]amino]-4-nitrophenol
—— 3-[(Z)-(pyridin-2-ylhydrazinylidene)methyl]phenol —— C12H11N3O
3-[(Z)-(pyridin-2-ylhydrazinylidene)methyl]phenol
—— Cambridge id 5622609 —— C19H13N3O4S
Cambridge id 5622609
—— 1-(3-Chloro-2,4-dihydroxyphenyl)-3-methylbutan-2-one —— C11H13ClO3
1-(3-Chloro-2,4-dihydroxyphenyl)-3-methylbutan-2-one
—— 2-[Amino(piperidin-4-ylidene)methyl]-5-fluorophenol —— C12H15FN2O
2-[Amino(piperidin-4-ylidene)methyl]-5-fluorophenol
—— 2-[2-[5-(1,3-Oxazol-5-yl)thiophen-2-yl]sulfonyl-5-pyridin-3-yl-1,3-dihydropyrazol-3-yl]phenol —— C21H16N4O4S2
2-[2-[5-(1,3-Oxazol-5-yl)thiophen-2-yl]sulfonyl-5-pyridin-3-yl-1,3-dihydropyrazol-3-yl]phenol
—— N'-(3-Hydroxy-4-methoxybenzylidene)-2-(2-toluidino)acetohydrazide 303066-03-7 C17H19N3O3
N'-(3-Hydroxy-4-methoxybenzylidene)-2-(2-toluidino)acetohydrazide
—— 3-(Hydroxymethyl)-6-methylbenzene-1,2,4,5-tetrol —— C8H10O5
3-(Hydroxymethyl)-6-methylbenzene-1,2,4,5-tetrol
—— 2-(Prop-2-ynylideneamino)benzene-1,4-diol —— C9H7NO2
2-(Prop-2-ynylideneamino)benzene-1,4-diol
—— 5-[(Z)-[(4,6-dipyrrolidin-1-yl-1,3,5-triazin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol —— C19H25N7O2
5-[(Z)-[(4,6-dipyrrolidin-1-yl-1,3,5-triazin-2-yl)hydrazinylidene]methyl]-2-methoxyphenol
—— N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-2-[(4-methylphenyl)amino]acetohydrazide (non-preferred name) —— C17H19N3O3
N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]-2-[(4-methylphenyl)amino]acetohydrazide (non-preferred name)
—— 1-Dimethoxyphosphoryl-3-(4-hydroxy-3-methylphenyl)propan-2-one —— C12H17O5P
1-Dimethoxyphosphoryl-3-(4-hydroxy-3-methylphenyl)propan-2-one
—— 2-[(2-Hydroxyphenyl)iminomethyl]propanedioic acid —— C10H9NO5
2-[(2-Hydroxyphenyl)iminomethyl]propanedioic acid
—— 4-nitro-2-[[(E)-2-nitroethenyl]amino]phenol —— C8H7N3O5
4-nitro-2-[[(E)-2-nitroethenyl]amino]phenol
—— 4-bromo-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]benzamide —— C14H10BrN3O4
4-bromo-N-[(E)-(5-hydroxy-2-nitrophenyl)methylideneamino]benzamide
—— 2-methoxy-5-[(E)-(phenylhydrazinylidene)methyl]phenol 5475-23-0 C14H14N2O2
2-methoxy-5-[(E)-(phenylhydrazinylidene)methyl]phenol
—— 2-chloro-4-nitro-6-[[(E)-2-nitroethenyl]amino]phenol —— C8H6ClN3O5
2-chloro-4-nitro-6-[[(E)-2-nitroethenyl]amino]phenol
—— 4-Bromo-2-methoxy-6-{[4-(3-phenyl-2-propen-1-yl)-1-piperazinyl]methyl}phenol —— C21H25BrN2O2
4-Bromo-2-methoxy-6-{[4-(3-phenyl-2-propen-1-yl)-1-piperazinyl]methyl}phenol
—— (E)-5-(5-Chloro-2-hydroxybenzylidene)-2-mercaptothiazol-4(5H)-one —— C10H6ClNO2S2
(E)-5-(5-Chloro-2-hydroxybenzylidene)-2-mercaptothiazol-4(5H)-one
—— 4-[1-[4-(2-Morpholin-4-ylethyl)piperazin-1-yl]ethyl]phenol —— C18H29N3O2
4-[1-[4-(2-Morpholin-4-ylethyl)piperazin-1-yl]ethyl]phenol
—— 2-(5-bromo-2-hydroxy-3-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one —— C16H8BrN3O4S
2-(5-bromo-2-hydroxy-3-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
—— (2E,5Z)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one —— C18H18N4O3S2
(2E,5Z)-2-[(5-ethyl-1,3,4-thiadiazol-2-yl)imino]-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-prop-2-enyl-1,3-thiazolidin-4-one
—— 2-(2-Bromo-5-chloro-4,6-dimethylpyridin-3-yl)-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enenitrile —— C16H11BrClN3O4
2-(2-Bromo-5-chloro-4,6-dimethylpyridin-3-yl)-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enenitrile
—— (Z)-3-(1,1-dioxidotetrahydrothiophen-3-yl)-5-(4-hydroxybenzylidene)-2-thioxothiazolidin-4-one —— C14H13NO4S3
(Z)-3-(1,1-dioxidotetrahydrothiophen-3-yl)-5-(4-hydroxybenzylidene)-2-thioxothiazolidin-4-one
—— 4-(3-Hydroxy-4-methoxyphenyl)-3-methylbutanal —— C12H16O3
4-(3-Hydroxy-4-methoxyphenyl)-3-methylbutanal
—— 3-[1-[1-[2,3-Bis(trihydroxymethyl)cyclopropyl]-3-methylbutyl]cyclobutyl]-6-chlorobenzene-1,2,4,5-tetrol —— C20H29ClO10
3-[1-[1-[2,3-Bis(trihydroxymethyl)cyclopropyl]-3-methylbutyl]cyclobutyl]-6-chlorobenzene-1,2,4,5-tetrol
—— 2-[[[1-(Tert-butylamino)-2-hydroxyethyl]amino]methyl]phenol —— C13H22N2O2
2-[[[1-(Tert-butylamino)-2-hydroxyethyl]amino]methyl]phenol
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione —— C14H14N2O4S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione
—— N-[(Z)-(4-bromophenyl)methylideneamino]-2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetamide —— C18H19BrN2O2S
N-[(Z)-(4-bromophenyl)methylideneamino]-2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetamide
—— 3-[4-[(3-butyl-2,4-dihydroxyphenyl)methyldiazenyl]phenyl]-4-methyl-4,5-dihydro-1H-pyridazin-6-one —— C22H26N4O3
3-[4-[(3-butyl-2,4-dihydroxyphenyl)methyldiazenyl]phenyl]-4-methyl-4,5-dihydro-1H-pyridazin-6-one