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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
—— 2-[2-[(2-Hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]benzoic acid —— C15H14N2O4
2-[2-[(2-Hydroxy-3-methoxyphenyl)methylidene]hydrazinyl]benzoic acid
—— 1-[(3-Hydroxy-4-methoxyphenyl)methylideneamino]-3-propan-2-ylthiourea —— C12H17N3O2S
1-[(3-Hydroxy-4-methoxyphenyl)methylideneamino]-3-propan-2-ylthiourea
—— methyl N'-benzyl-N-butyl-N-[(4-hydroxyphenyl)methyl]carbamimidothioate —— C20H26N2OS
methyl N'-benzyl-N-butyl-N-[(4-hydroxyphenyl)methyl]carbamimidothioate
—— 3-Benzyl-1-butyl-1-[(4-hydroxyphenyl)methyl]thiourea —— C19H24N2OS
3-Benzyl-1-butyl-1-[(4-hydroxyphenyl)methyl]thiourea
—— 4-{2-[(2,5-Dimethylphenyl)amino]-1,3-thiazol-4-yl}benzene-1,2-diol —— C17H16N2O2S
4-{2-[(2,5-Dimethylphenyl)amino]-1,3-thiazol-4-yl}benzene-1,2-diol
—— 7-Benzyl-2-(3-hydroxy-4-methoxyphenyl)-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol —— C23H23N3O3S
7-Benzyl-2-(3-hydroxy-4-methoxyphenyl)-1,2,5,6,7,8-hexahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ol
—— 4-({[5-(1,3-benzodioxol-5-yl)-1-methyl-1H-imidazol-2-yl]amino}methyl)-2-methoxyphenol —— C19H19N3O4
4-({[5-(1,3-benzodioxol-5-yl)-1-methyl-1H-imidazol-2-yl]amino}methyl)-2-methoxyphenol
—— 3,5-Dimethyl 1-[(adamantan-1-YL)methyl]-4-(4-hydroxy-3-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate —— C27H33NO6
3,5-Dimethyl 1-[(adamantan-1-YL)methyl]-4-(4-hydroxy-3-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylate
—— (4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H19N7O4
(4R)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-1-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 2-[(4-Hydroxy-2-methylanilino)methylidene]-6-methylcyclohexan-1-one —— C15H19NO2
2-[(4-Hydroxy-2-methylanilino)methylidene]-6-methylcyclohexan-1-one
—— 2-(2-hydroxyphenyl)-4-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine —— C16H16N4O
2-(2-hydroxyphenyl)-4-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine
—— 2-[(2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidenehydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl]-N-phenylacetamide —— C19H18N4O4S
2-[(2Z)-2-[(4-hydroxy-3-methoxyphenyl)methylidenehydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl]-N-phenylacetamide
—— 5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO3S2
5-[(3-Hydroxy-4-methoxyphenyl)methylidene]-3-(4-methylphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— N'-(4-tert-butylcyclohexylidene)-3,4,5-trihydroxybenzohydrazide —— C17H24N2O4
N'-(4-tert-butylcyclohexylidene)-3,4,5-trihydroxybenzohydrazide
—— 2-Methyl-6-(octylsulfanylmethyl)phenol —— C16H26OS
2-Methyl-6-(octylsulfanylmethyl)phenol
—— 5,11,17,23-Tetrakis(dicyclohexylmethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol —— C80H112O4
5,11,17,23-Tetrakis(dicyclohexylmethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— propan-2-yl 2-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O4S
propan-2-yl 2-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-7-methyl-3-oxo-5-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-Butyl-5-[(2-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one —— C20H20N2O2S
3-Butyl-5-[(2-hydroxyphenyl)methylidene]-2-phenylimino-1,3-thiazolidin-4-one
—— methyl (Z)-3-fluoro-3-(4-hydroxy-3-methylphenyl)sulfanyl-2-(trifluoromethyl)prop-2-enoate —— C12H10F4O3S
methyl (Z)-3-fluoro-3-(4-hydroxy-3-methylphenyl)sulfanyl-2-(trifluoromethyl)prop-2-enoate
—— 4-methoxy-2-[(Z,2S)-pent-3-en-2-yl]phenol —— C12H16O2
4-methoxy-2-[(Z,2S)-pent-3-en-2-yl]phenol
—— 3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one —— C26H24N2O2S
3-(4-Ethylphenyl)-2-(4-ethylphenyl)imino-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[(2-Hydroxy-5-nitroanilino)methylidene]-3-methyl-1-oxopyrido[1,2-a]benzimidazole-4-carbonitrile —— C20H13N5O4
2-[(2-Hydroxy-5-nitroanilino)methylidene]-3-methyl-1-oxopyrido[1,2-a]benzimidazole-4-carbonitrile
—— 1-(3-Chlorophenyl)-4-[(3,5-dibromo-2-hydroxyphenyl)methylidene]pyrazolidine-3,5-dione —— C16H9Br2ClN2O3
1-(3-Chlorophenyl)-4-[(3,5-dibromo-2-hydroxyphenyl)methylidene]pyrazolidine-3,5-dione
—— 4-[4-(3,4-dihydro-2H-1,5-benzodioxepin-6-yl)-3-methyl-1,2-oxazol-5-yl]benzene-1,3-diol —— C19H17NO5
4-[4-(3,4-dihydro-2H-1,5-benzodioxepin-6-yl)-3-methyl-1,2-oxazol-5-yl]benzene-1,3-diol
—— (5Z)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one —— C16H18N2O3S
(5Z)-2-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5-[(3-hydroxyphenyl)methylidene]-1,3-thiazol-4-one
—— 2,4-bis[(2S)-pentan-2-yl]phenol —— C16H26O
2,4-bis[(2S)-pentan-2-yl]phenol
—— 5,6-Dimethyl 7-(2-hydroxy-5-nitrophenyl)-2-oxo-2H,3H,5H,6H,7H-thiopyrano[2,3-D][1,3]thiazole-5,6-dicarboxylate —— C16H14N2O8S2
5,6-Dimethyl 7-(2-hydroxy-5-nitrophenyl)-2-oxo-2H,3H,5H,6H,7H-thiopyrano[2,3-D][1,3]thiazole-5,6-dicarboxylate
—— [4-(4-Hydroxyphenyl)but-1-en-2-ylamino]thiourea —— C11H15N3OS
[4-(4-Hydroxyphenyl)but-1-en-2-ylamino]thiourea
—— Allyl 5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-((2-oxo-2-(m-tolylamino)ethyl)thio)-1,4-dihydropyridine-3-carboxylate —— C27H27N3O5S
Allyl 5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-((2-oxo-2-(m-tolylamino)ethyl)thio)-1,4-dihydropyridine-3-carboxylate
—— (2Z,6R)-2-[(4-hydroxyphenyl)methylidene]-6-(piperidin-1-ylmethyl)cyclohexan-1-one —— C19H25NO2
(2Z,6R)-2-[(4-hydroxyphenyl)methylidene]-6-(piperidin-1-ylmethyl)cyclohexan-1-one
—— (2E,6Z)-2,6-bis[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]cyclohexan-1-one —— C26H26O5
(2E,6Z)-2,6-bis[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]cyclohexan-1-one
—— N-<β-(3.4-Dihydroxyphenyl)-ethyl>-cyclopropancarboxamid 42600-72-6 C12H15NO3
N-<β-(3.4-Dihydroxyphenyl)-ethyl>-cyclopropancarboxamid
—— (2Z,6S)-2-[(4-hydroxyphenyl)methylidene]-6-(piperidin-1-ylmethyl)cyclohexan-1-one —— C19H25NO2
(2Z,6S)-2-[(4-hydroxyphenyl)methylidene]-6-(piperidin-1-ylmethyl)cyclohexan-1-one
—— (2E,6Z)-2-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]-6-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]cyclohexan-1-one —— C26H26O5
(2E,6Z)-2-[(Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]-6-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enylidene]cyclohexan-1-one
—— N-[(Z)-2-(2,5-dihydroxyphenyl)ethenyl]-N-methylformamide —— C10H11NO3
N-[(Z)-2-(2,5-dihydroxyphenyl)ethenyl]-N-methylformamide
—— 3-(1,3-Benzothiazol-2-ylamino)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H10N4O4S3
3-(1,3-Benzothiazol-2-ylamino)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (5E)-5-[(2,3-dihydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O4S2
(5E)-5-[(2,3-dihydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 6-Amino-8-(4-HO-PH)2-ME-2,3,8,8A-tetrahydro-5,7,7(1H)isoquinolinetricarbonitrile —— C19H17N5O
6-Amino-8-(4-HO-PH)2-ME-2,3,8,8A-tetrahydro-5,7,7(1H)isoquinolinetricarbonitrile
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H22N2O4S2
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-N'-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]decanediamide —— C26H34N4O6
N-[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-N'-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]decanediamide
—— (5E)-5-[(2-hydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H20N2O3S2
(5E)-5-[(2-hydroxyphenyl)methylidene]-3-(3-morpholin-4-ylpropyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl 2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl 2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(4-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 5-[(3-Bromo-4-hydroxyphenyl)methylidene]-2-(3-bromophenyl)imino-1,3-thiazolidin-4-one —— C16H10Br2N2O2S
5-[(3-Bromo-4-hydroxyphenyl)methylidene]-2-(3-bromophenyl)imino-1,3-thiazolidin-4-one
—— 2-(4-Chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one —— C18H15ClN2O2S
2-(4-Chlorophenyl)imino-5-[(4-hydroxy-3,5-dimethylphenyl)methylidene]-1,3-thiazolidin-4-one
—— 2-[[(2R,6R)-2,6-dimethylmorpholin-4-yl]methyl]-6-methoxy-4-prop-2-enylphenol —— C17H25NO3
2-[[(2R,6R)-2,6-dimethylmorpholin-4-yl]methyl]-6-methoxy-4-prop-2-enylphenol
—— N-(3-chloro-4-methoxyphenyl)-2-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C20H17ClN2O6S
N-(3-chloro-4-methoxyphenyl)-2-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— 2-(5-Chloro-2-hydroxyphenyl)-3-(2-morpholin-4-ylethyl)-1,3-thiazinan-4-one —— C16H21ClN2O3S
2-(5-Chloro-2-hydroxyphenyl)-3-(2-morpholin-4-ylethyl)-1,3-thiazinan-4-one
—— (2S)-2-[3-(2,5-dihydroxyphenyl)propanoyl]cyclopentan-1-one —— C14H16O4
(2S)-2-[3-(2,5-dihydroxyphenyl)propanoyl]cyclopentan-1-one
—— 5-(5-Hydroxy-2-nitrophenyl)imino-2-phenylimino-1,3-thiazolidin-4-one —— C15H10N4O4S
5-(5-Hydroxy-2-nitrophenyl)imino-2-phenylimino-1,3-thiazolidin-4-one
—— [(S)-(2-hydroxyphenyl)-[2-[[(R)-(2-hydroxyphenyl)-phosphonomethyl]amino]ethylamino]methyl]phosphonic acid —— C16H22N2O8P2
[(S)-(2-hydroxyphenyl)-[2-[[(R)-(2-hydroxyphenyl)-phosphonomethyl]amino]ethylamino]methyl]phosphonic acid