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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
—— (4-Hydroxy-3-methoxyphenyl)methyl-methylazanium —— C9H14NO2+
(4-Hydroxy-3-methoxyphenyl)methyl-methylazanium
—— 2-[(4aR,6R,6aS,10bS)-2,3,4,4a,6,6a,7,8,9,10b-decahydro-1H-benzo[c]chromen-6-yl]phenol —— C19H24O2
2-[(4aR,6R,6aS,10bS)-2,3,4,4a,6,6a,7,8,9,10b-decahydro-1H-benzo[c]chromen-6-yl]phenol
—— 2-[(5S)-3-thiophen-2-yl-4,5-dihydro-1H-pyrazol-5-yl]phenol —— C13H12N2OS
2-[(5S)-3-thiophen-2-yl-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— 2-[(5R)-3-phenyl-4,5-dihydro-1H-pyrazol-5-yl]phenol —— C15H14N2O
2-[(5R)-3-phenyl-4,5-dihydro-1H-pyrazol-5-yl]phenol
—— (2S)-3-(4-hydroxy-3-methoxyphenyl)-N-phenyl-2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)propanamide —— C17H16N5O3-
(2S)-3-(4-hydroxy-3-methoxyphenyl)-N-phenyl-2-(1,2,3-triaza-4-azanidacyclopenta-2,5-dien-5-yl)propanamide
—— 5-[(1S)-1-(2,2-dimethoxyethylamino)ethyl]-2-methoxyphenol —— C13H21NO4
5-[(1S)-1-(2,2-dimethoxyethylamino)ethyl]-2-methoxyphenol
—— (3-Hydroxy-4-methoxyphenyl)methyl-(2,2,2-trimethoxyethyl)azanium —— C13H22NO5+
(3-Hydroxy-4-methoxyphenyl)methyl-(2,2,2-trimethoxyethyl)azanium
—— 2,2-Dimethoxyethyl-[(4-hydroxy-3-methoxyphenyl)methyl]azanium —— C12H20NO4+
2,2-Dimethoxyethyl-[(4-hydroxy-3-methoxyphenyl)methyl]azanium
—— (4S)-4-[(4-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one —— C17H16N2O2
(4S)-4-[(4-hydroxyphenyl)methyl]-5-methyl-2-phenyl-4H-pyrazol-3-one
—— methyl (2S)-2-chloro-3,3,3-trifluoro-2-(4-hydroxyphenyl)propanoate —— C10H8ClF3O3
methyl (2S)-2-chloro-3,3,3-trifluoro-2-(4-hydroxyphenyl)propanoate
—— 3-Butyl-5-{2-hydroxy-3-nitrobenzylidene}-2-thioxo-1,3-thiazolidin-4-one —— C14H14N2O4S2
3-Butyl-5-{2-hydroxy-3-nitrobenzylidene}-2-thioxo-1,3-thiazolidin-4-one
—— prop-2-enyl (6S)-6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate —— C17H19ClN2O5
prop-2-enyl (6S)-6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— 2-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetate —— C13H10NO5S2-
2-[(5E)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetate
—— 2-(2-cyanophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide —— C17H15N3O4
2-(2-cyanophenoxy)-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]acetamide
—— ethyl (5R)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18ClN3O6S
ethyl (5R)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (5S)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18ClN3O6S
ethyl (5S)-5-(4-chlorophenyl)-2-[(4-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-5-(pyrrolidin-1-ium-1-ylmethyl)triazole-4-carboxamide —— C17H20N9O3+
1-(4-amino-1,2,5-oxadiazol-3-yl)-N-[(Z)-(3-hydroxyphenyl)methylideneamino]-5-(pyrrolidin-1-ium-1-ylmethyl)triazole-4-carboxamide
—— 2-(2-Bromo-4-hydroxy-5-methoxyphenyl)acetate —— C9H8BrO4-
2-(2-Bromo-4-hydroxy-5-methoxyphenyl)acetate
—— (4-hydroxy-3,5-dimethoxyphenyl)methyl-[[(2S)-oxolan-2-yl]methyl]azanium —— C14H22NO4+
(4-hydroxy-3,5-dimethoxyphenyl)methyl-[[(2S)-oxolan-2-yl]methyl]azanium
—— (2R,7S)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C22H28N2O4S
(2R,7S)-7-tert-butyl-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— (2S,7R)-7-tert-butyl-2-(2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one —— C21H26N2O3S
(2S,7R)-7-tert-butyl-2-(2-hydroxy-3-methoxyphenyl)-2,3,5,6,7,8-hexahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
—— 4-[(1R)-1-(2-hydroxyethylsulfanyl)-2-nitroethyl]phenol —— C10H13NO4S
4-[(1R)-1-(2-hydroxyethylsulfanyl)-2-nitroethyl]phenol
—— 2-ethoxyethyl (6S)-6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate —— C18H23ClN2O6
2-ethoxyethyl (6S)-6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— methyl (2R)-2-(2,4-dihydroxyphenyl)sulfanyl-2,3,3,3-tetrafluoropropanoate —— C10H8F4O4S
methyl (2R)-2-(2,4-dihydroxyphenyl)sulfanyl-2,3,3,3-tetrafluoropropanoate
—— 4-[(1S)-1-(2-hydroxyethylsulfanyl)-2-nitroethyl]phenol —— C10H13NO4S
4-[(1S)-1-(2-hydroxyethylsulfanyl)-2-nitroethyl]phenol
—— methyl (2S)-2-(2,4-dihydroxyphenyl)sulfanyl-2,3,3,3-tetrafluoropropanoate —— C10H8F4O4S
methyl (2S)-2-(2,4-dihydroxyphenyl)sulfanyl-2,3,3,3-tetrafluoropropanoate
—— (6S)-10-ethyl-4-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-1,4,10-triazaspiro[5.6]dodecan-9-one —— C20H31N3O3
(6S)-10-ethyl-4-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-1,4,10-triazaspiro[5.6]dodecan-9-one
—— (6R)-10-ethyl-4-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-1,4,10-triazaspiro[5.6]dodecan-9-one —— C20H31N3O3
(6R)-10-ethyl-4-[(3-hydroxy-4-methoxyphenyl)methyl]-1-methyl-1,4,10-triazaspiro[5.6]dodecan-9-one
—— (5R)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C30H27N3O5S
(5R)-5-(4-ethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 4-hydroxy-3-methoxy-N'-[(Z)-1-(5-nitrotetrazol-2-yl)prop-1-en-2-yl]benzohydrazide —— C12H13N7O5
4-hydroxy-3-methoxy-N'-[(Z)-1-(5-nitrotetrazol-2-yl)prop-1-en-2-yl]benzohydrazide
—— (2S)-2-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C15H14NO5S2-
(2S)-2-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
—— (4R,6S)-4-(2-hydroxy-5-nitrophenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid —— C13H12N4O5
(4R,6S)-4-(2-hydroxy-5-nitrophenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid
—— Benzyl-[(4-hydroxy-3-methoxyphenyl)methyl]azanium —— C15H18NO2+
Benzyl-[(4-hydroxy-3-methoxyphenyl)methyl]azanium
—— (8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,5,12,14-tetraoxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one —— C20H16O8
(8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-2,5,12,14-tetraoxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one
—— (4S)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide —— C18H16N4O4S
(4S)-4-(2-hydroxy-5-nitrophenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 3-[[(2R)-2-hydroxy-2-phenylethyl]iminomethyl]phenol —— C15H15NO2
3-[[(2R)-2-hydroxy-2-phenylethyl]iminomethyl]phenol
—— 3-[[(2S)-2-hydroxy-2-phenylethyl]iminomethyl]phenol —— C15H15NO2
3-[[(2S)-2-hydroxy-2-phenylethyl]iminomethyl]phenol
—— 2-adamantyl-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]azanium —— C20H30NO+
2-adamantyl-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]azanium
—— 4-Methoxy-2-[[4-[(3-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C19H25N3O4+2
4-Methoxy-2-[[4-[(3-nitrophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— (2R)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile —— C19H17N3O3S
(2R)-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
—— [5-(aminomethyl)-2-methoxyphenyl]oxidanium —— C8H12NO2+
[5-(aminomethyl)-2-methoxyphenyl]oxidanium
—— 2-(5-Bromo-2-hydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C16H23BrN2O2+2
2-(5-Bromo-2-hydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— (2R)-2-[4-[(R)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile —— C22H26N4O4+2
(2R)-2-[4-[(R)-cyano-(4-hydroxy-3-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]-2-(4-hydroxy-3-methoxyphenyl)acetonitrile
—— (4R)-4-(2-hydroxyphenyl)heptanal —— C13H18O2
(4R)-4-(2-hydroxyphenyl)heptanal
—— (4S)-4-(2-hydroxyphenyl)heptanal —— C13H18O2
(4S)-4-(2-hydroxyphenyl)heptanal
—— 2-[[4-[(2-Hydroxy-3-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-6-methoxyphenol —— C20H28N2O4+2
2-[[4-[(2-Hydroxy-3-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-6-methoxyphenol
—— Furan-2-ylmethyl-[(2-hydroxy-3-methoxyphenyl)methyl]azanium —— C13H16NO3+
Furan-2-ylmethyl-[(2-hydroxy-3-methoxyphenyl)methyl]azanium
—— cycloheptyl-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]azanium —— C17H28NO+
cycloheptyl-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]azanium
—— 2-(5-Bromo-2-hydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one —— C16H21BrN2O2+2
2-(5-Bromo-2-hydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-one
—— 2-[(2S,4R,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-3-ium-2-yl]phenol —— C17H20NO2+
2-[(2S,4R,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-3-ium-2-yl]phenol