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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
—— (5R)-3-[(E,2R,4R)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione —— C21H27NO5
(5R)-3-[(E,2R,4R)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione
—— (5R)-3-[(E,2S,4S)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione —— C21H27NO5
(5R)-3-[(E,2S,4S)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione
—— (5R)-3-[(E,2R,4S)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione —— C21H27NO5
(5R)-3-[(E,2R,4S)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione
—— [(R)-(2-hydroxyphenyl)-[2-[[(R)-(2-hydroxyphenyl)-phosphonomethyl]amino]ethylamino]methyl]phosphonic acid —— C16H22N2O8P2
[(R)-(2-hydroxyphenyl)-[2-[[(R)-(2-hydroxyphenyl)-phosphonomethyl]amino]ethylamino]methyl]phosphonic acid
—— (5R)-3-[(E,2S,4R)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione —— C21H27NO5
(5R)-3-[(E,2S,4R)-1-hydroxy-2,4-dimethyloct-6-enylidene]-5-[(S)-hydroxy-(4-hydroxyphenyl)methyl]pyrrolidine-2,4-dione
—— 2-[(E)-[[4-(2,5-dimethylanilino)-6-morpholin-4-yl-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-4,6-dinitrophenol —— C22H23N9O6
2-[(E)-[[4-(2,5-dimethylanilino)-6-morpholin-4-yl-1,3,5-triazin-2-yl]hydrazinylidene]methyl]-4,6-dinitrophenol
—— 3,4,5-trihydroxy-N-[1-(5-methylfuran-2-yl)ethylideneamino]benzamide —— C14H14N2O5
3,4,5-trihydroxy-N-[1-(5-methylfuran-2-yl)ethylideneamino]benzamide
—— (5R)-5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-2,3-diol —— C12H17NO2
(5R)-5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-2,3-diol
—— 4-[2-[6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1H-pyridin-2-ylidene]ethylidene]-2-methoxycyclohexa-2,5-dien-1-one —— C23H21NO4
4-[2-[6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1H-pyridin-2-ylidene]ethylidene]-2-methoxycyclohexa-2,5-dien-1-one
—— (5S)-5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-2,3-diol —— C12H17NO2
(5S)-5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-2,3-diol
—— (5R)-5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1,2-diol —— C12H17NO2
(5R)-5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1,2-diol
—— ethyl N-[(2-hydroxy-5-methylphenyl)methylideneamino]carbamate —— C11H14N2O3
ethyl N-[(2-hydroxy-5-methylphenyl)methylideneamino]carbamate
—— 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-[(3-bromophenyl)methylideneamino]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H10Br2N2O2S2
5-[(5-Bromo-2-hydroxyphenyl)methylidene]-3-[(3-bromophenyl)methylideneamino]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-fluorophenyl)imino-1,3-thiazolidin-4-one —— C17H12BrFN2O3S
5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-fluorophenyl)imino-1,3-thiazolidin-4-one
—— N-[(3-hydroxy-4-nitrophenyl)methylideneamino]-6-methylpyridine-3-carboxamide —— C14H12N4O4
N-[(3-hydroxy-4-nitrophenyl)methylideneamino]-6-methylpyridine-3-carboxamide
—— 2-(4-Chlorophenyl)sulfonyl-3-(2-hydroxy-3-methoxyphenyl)prop-2-enenitrile —— C16H12ClNO4S
2-(4-Chlorophenyl)sulfonyl-3-(2-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— 2-(4-Chlorophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile —— C16H12ClNO4S
2-(4-Chlorophenyl)sulfonyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile
—— 2-[(1S)-1-hydroxyprop-2-enyl]phenol —— C9H10O2
2-[(1S)-1-hydroxyprop-2-enyl]phenol
—— 5-(3,4,5-trihydroxyphenyl)-γ-valerolactone 264277-86-3 C11H12O5
5-(3,4,5-trihydroxyphenyl)-γ-valerolactone
—— N-[1-(3-hydroxyphenyl)ethylideneamino]nonanamide —— C17H26N2O2
N-[1-(3-hydroxyphenyl)ethylideneamino]nonanamide
—— 4-[(1S)-2-amino-1-hydroxyethyl]-2-bromophenol —— C8H10BrNO2
4-[(1S)-2-amino-1-hydroxyethyl]-2-bromophenol
—— 4-[(1S)-1-hydroxy-2-imidazol-1-ylethyl]benzene-1,2-diol —— C11H12N2O3
4-[(1S)-1-hydroxy-2-imidazol-1-ylethyl]benzene-1,2-diol
—— 4-[(1R)-1-hydroxy-2-imidazol-1-ylethyl]benzene-1,2-diol —— C11H12N2O3
4-[(1R)-1-hydroxy-2-imidazol-1-ylethyl]benzene-1,2-diol
—— 4-[(1S)-1-hydroxy-2-imidazol-1-ylethyl]phenol —— C11H12N2O2
4-[(1S)-1-hydroxy-2-imidazol-1-ylethyl]phenol
—— 4-[5-[(3-Hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C14H12NO4S2-
4-[5-[(3-Hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
—— (2S)-4-amino-2-(2-hydroxy-5-nitrophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-2H-chromene-3-carbonitrile —— C18H17N3O5
(2S)-4-amino-2-(2-hydroxy-5-nitrophenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-2H-chromene-3-carbonitrile
—— 1-[(2-Hydroxyphenyl)methyl]pyrrolidin-2-one —— C11H13NO2
1-[(2-Hydroxyphenyl)methyl]pyrrolidin-2-one
—— methyl (4R)-6-amino-5-cyano-4-(3,5-dibromo-4-hydroxyphenyl)-2-methyl-4H-pyran-3-carboxylate —— C15H12Br2N2O4
methyl (4R)-6-amino-5-cyano-4-(3,5-dibromo-4-hydroxyphenyl)-2-methyl-4H-pyran-3-carboxylate
—— N'-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)ethanimidamide —— C10H14N2O4
N'-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)ethanimidamide
—— 1-Benzyl-6-hydroxy-5-[(4-hydroxy-2-methylphenyl)iminomethyl]-4-methyl-2-oxopyridine-3-carbonitrile —— C22H19N3O3
1-Benzyl-6-hydroxy-5-[(4-hydroxy-2-methylphenyl)iminomethyl]-4-methyl-2-oxopyridine-3-carbonitrile
—— ethyl (4R,7R)-2-amino-4-(4-hydroxy-3-methoxyphenyl)-5-oxo-7-phenyl-4,6,7,8-tetrahydrochromene-3-carboxylate —— C25H25NO6
ethyl (4R,7R)-2-amino-4-(4-hydroxy-3-methoxyphenyl)-5-oxo-7-phenyl-4,6,7,8-tetrahydrochromene-3-carboxylate
—— (7R)-7-(4,5-dihydro-1H-imidazol-2-yl)bicyclo[4.2.0]octa-1(6),2,4-triene-2,3-diol —— C11H12N2O2
(7R)-7-(4,5-dihydro-1H-imidazol-2-yl)bicyclo[4.2.0]octa-1(6),2,4-triene-2,3-diol
—— 4-chloro-2-(N-hydroxy-C-propylcarbonimidoyl)phenol —— C10H12ClNO2
4-chloro-2-(N-hydroxy-C-propylcarbonimidoyl)phenol
—— 4-[5-[(4-Hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C14H12NO4S2-
4-[5-[(4-Hydroxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
—— ethyl (2Z,5R)-2-benzylidene-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H20N2O4S
ethyl (2Z,5R)-2-benzylidene-5-(4-hydroxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3,4,5-trihydroxy-N-[(E)-1-(5-methyl-3-nitropyrazol-1-yl)propan-2-ylideneamino]benzamide —— C14H15N5O6
3,4,5-trihydroxy-N-[(E)-1-(5-methyl-3-nitropyrazol-1-yl)propan-2-ylideneamino]benzamide
—— 2-(1,3-Dibenzyl-1,3-diazinane-1,3-diium-2-yl)-4-nitrophenol —— C24H27N3O3+2
2-(1,3-Dibenzyl-1,3-diazinane-1,3-diium-2-yl)-4-nitrophenol
—— N-[[1-[(2-chlorophenyl)methyl]-2-methylindol-3-yl]methylideneamino]-2-hydroxy-3-nitrobenzamide —— C24H19ClN4O4
N-[[1-[(2-chlorophenyl)methyl]-2-methylindol-3-yl]methylideneamino]-2-hydroxy-3-nitrobenzamide
—— 4-[(2-Hydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one —— C11H9NO3
4-[(2-Hydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one
—— 4-[(2,4-Dihydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one —— C11H9NO4
4-[(2,4-Dihydroxyphenyl)methylidene]-3-methylidene-1,2-oxazolidin-5-one
—— N-(2-hydroxy-4-nitrophenyl)-2-oxo-1-oxaspiro[4.5]decane-4-carboxamide —— C16H18N2O6
N-(2-hydroxy-4-nitrophenyl)-2-oxo-1-oxaspiro[4.5]decane-4-carboxamide
—— (5S)-3-hydroxy-5-(4-hydroxyphenyl)cyclohex-2-en-1-one —— C12H12O3
(5S)-3-hydroxy-5-(4-hydroxyphenyl)cyclohex-2-en-1-one
—— 3,4,5-trihydroxy-N-(thiophen-2-ylmethylideneamino)benzamide —— C12H10N2O4S
3,4,5-trihydroxy-N-(thiophen-2-ylmethylideneamino)benzamide
—— 4-[2-[(S)-methylsulfinyl]ethyl]benzene-1,2-diol —— C9H12O3S
4-[2-[(S)-methylsulfinyl]ethyl]benzene-1,2-diol
—— ethyl 5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H26N2O6S
ethyl 5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 8-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione —— C21H21ClO4
8-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-ethenyl-2,8a-dimethyl-5,8-dihydro-4aH-naphthalene-1,4-dione
—— Methyl 5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methylidene-4-oxopyrrolidine-3-carboxylate —— C15H15NO5
Methyl 5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methylidene-4-oxopyrrolidine-3-carboxylate
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-[[(2S)-2-methylpiperidin-1-yl]methyl]triazole-4-carboxamide —— C20H25N9O4
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-5-[[(2S)-2-methylpiperidin-1-yl]methyl]triazole-4-carboxamide
—— ethyl 2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H28N2O6S
ethyl 2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-5-(3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(5S)-5-methyl-4,5-dihydro-1H-imidazol-2-yl]phenol —— C10H12N2O
3-[(5S)-5-methyl-4,5-dihydro-1H-imidazol-2-yl]phenol