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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
—— N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-6-methylpyridine-3-carbohydrazide —— C14H12N4O4
N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]-6-methylpyridine-3-carbohydrazide
—— N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(3-methylphenoxy)acetamide —— C16H15N3O5
N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(3-methylphenoxy)acetamide
—— N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2-methylphenoxy)acetamide —— C16H15N3O5
N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]-2-(2-methylphenoxy)acetamide
—— (4E)-3-hydroxy-4-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,5-dien-1-one —— C13H10N2O5
(4E)-3-hydroxy-4-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,5-dien-1-one
—— 4-tert-butyl-N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide —— C18H19N3O4
4-tert-butyl-N-[(Z)-(3-hydroxy-4-nitrophenyl)methylideneamino]benzamide
—— (2S)-N-[(2-hydroxyphenyl)methyl]-N-methyl-2-propan-2-ylsulfonylpropanamide —— C14H21NO4S
(2S)-N-[(2-hydroxyphenyl)methyl]-N-methyl-2-propan-2-ylsulfonylpropanamide
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylphenyl)-1,3-thiazol-4-one —— C18H15NO3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylphenyl)-1,3-thiazol-4-one
—— 3-(2-hydroxyphenyl)-N-[(Z)-(6-methylpyridin-2-yl)methylideneamino]propanamide —— C16H17N3O2
3-(2-hydroxyphenyl)-N-[(Z)-(6-methylpyridin-2-yl)methylideneamino]propanamide
—— 4-chloro-N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]benzohydrazide —— C14H10ClN3O4
4-chloro-N'-[(Z)-(5-hydroxy-2-nitrophenyl)methylidene]benzohydrazide
—— (E)-N-[2-(3,4-dihydroxyphenyl)ethenyl]formamide —— C9H9NO3
(E)-N-[2-(3,4-dihydroxyphenyl)ethenyl]formamide
—— 2-methoxy-4-[(2S)-1,3-thiazolidin-2-yl]phenol —— C10H13NO2S
2-methoxy-4-[(2S)-1,3-thiazolidin-2-yl]phenol
—— (4Z)-2-chloro-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-oxazol-5-one —— C11H8ClNO4
(4Z)-2-chloro-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-1,3-oxazol-5-one
—— 2-methoxy-4-[(2R)-1,3-thiazolidin-2-yl]phenol —— C10H13NO2S
2-methoxy-4-[(2R)-1,3-thiazolidin-2-yl]phenol
—— (5E)-2-[(dimethylamino)methyl]-5-[(4-hydroxyphenyl)methylidene]cyclopentan-1-one —— C15H19NO2
(5E)-2-[(dimethylamino)methyl]-5-[(4-hydroxyphenyl)methylidene]cyclopentan-1-one
—— 2-[(dimethylamino)methyl]-3-[(Z)-heptadec-10-enyl]-5-methoxybenzene-1,4-diol;hydrochloride —— C27H48ClNO3
2-[(dimethylamino)methyl]-3-[(Z)-heptadec-10-enyl]-5-methoxybenzene-1,4-diol;hydrochloride
—— 2-[(dimethylamino)methyl]-3-[(Z)-heptadec-10-enyl]-5-methoxybenzene-1,4-diol —— C27H47NO3
2-[(dimethylamino)methyl]-3-[(Z)-heptadec-10-enyl]-5-methoxybenzene-1,4-diol
—— (5E)-2-[(dimethylamino)methyl]-5-[(4-hydroxyphenyl)methylidene]cyclopentan-1-one;hydrochloride —— C15H20ClNO2
(5E)-2-[(dimethylamino)methyl]-5-[(4-hydroxyphenyl)methylidene]cyclopentan-1-one;hydrochloride
—— (7Z)-7-[(4-hydroxyphenyl)methylidene]-4'-methylspiro[2,4-dihydro-[1,3]thiazolo[3,2-b][1,2,4,5]tetrazine-3,1'-cyclohexane]-6-one —— C17H20N4O2S
(7Z)-7-[(4-hydroxyphenyl)methylidene]-4'-methylspiro[2,4-dihydro-[1,3]thiazolo[3,2-b][1,2,4,5]tetrazine-3,1'-cyclohexane]-6-one
—— methyl (4Z)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-propan-2-ylpyrrole-3-carboxylate —— C17H19NO4
methyl (4Z)-4-[(2-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-propan-2-ylpyrrole-3-carboxylate
—— methyl (4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-propan-2-ylpyrrole-3-carboxylate —— C18H21NO5
methyl (4Z)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-propan-2-ylpyrrole-3-carboxylate
—— (6Z)-6-[[[(2-hydroxy-3-methoxyphenyl)-[[(Z)-(5-methoxy-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]methyl]amino]methylidene]-2-methoxycyclohexa-2,4-dien-1-one —— C24H24N2O6
(6Z)-6-[[[(2-hydroxy-3-methoxyphenyl)-[[(Z)-(5-methoxy-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]methyl]amino]methylidene]-2-methoxycyclohexa-2,4-dien-1-one
—— 1-amino-3-[(E)-[1-(3-hydroxy-4-methoxyphenyl)-2-(3-hydroxy-2-oxo-1H-indol-3-yl)ethylidene]amino]urea —— C18H19N5O5
1-amino-3-[(E)-[1-(3-hydroxy-4-methoxyphenyl)-2-(3-hydroxy-2-oxo-1H-indol-3-yl)ethylidene]amino]urea
—— methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-1-[(4-methylphenyl)methyl]-5-oxopyrrole-3-carboxylate —— C23H23NO5
methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-1-[(4-methylphenyl)methyl]-5-oxopyrrole-3-carboxylate
—— (5E)-3-cyclohexyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C16H15Br2NO2S2
(5E)-3-cyclohexyl-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (E)-N-[2-(2,3-dihydroxyphenyl)ethenyl]formamide —— C9H9NO3
(E)-N-[2-(2,3-dihydroxyphenyl)ethenyl]formamide
—— methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-propan-2-ylpyrrole-3-carboxylate —— C18H21NO5
methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-propan-2-ylpyrrole-3-carboxylate
—— 4-[butylamino-(2-hydroxy-4-methoxyphenyl)methylidene]cyclohexa-2,5-dien-1-one —— C18H21NO3
4-[butylamino-(2-hydroxy-4-methoxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
—— (5Z)-3-cyclopropyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C14H13NO3S2
(5Z)-3-cyclopropyl-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— ethyl (2E,5R)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C22H19BrN2O5S2
ethyl (2E,5R)-2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 6-[[4-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,5-dien-1-ylidene]methylimino]-4-nitrocyclohexa-2,4-dien-1-one —— C20H14N4O6
6-[[4-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,5-dien-1-ylidene]methylimino]-4-nitrocyclohexa-2,4-dien-1-one
—— (5Z)-5-(ethoxymethylidene)-3-(4-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C12H11NO3S2
(5Z)-5-(ethoxymethylidene)-3-(4-hydroxyphenyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 5-butyl-2-[(E)-2-phenylethenyl]pyridine;2,4,6-trinitrophenol —— C23H22N4O7
5-butyl-2-[(E)-2-phenylethenyl]pyridine;2,4,6-trinitrophenol
—— 6-[(3-hydroxy-4-methylanilino)methylidene]cyclohexa-2,4-dien-1-one —— C14H13NO2
6-[(3-hydroxy-4-methylanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H10N2O4
6-[(2-hydroxy-4-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one —— C13H10N2O4
6-[(2-hydroxy-5-nitroanilino)methylidene]cyclohexa-2,4-dien-1-one
—— 2-[(E)-prop-1-enyl]sulfanylpyridine;2,4,6-trinitrophenol —— C14H12N4O7S
2-[(E)-prop-1-enyl]sulfanylpyridine;2,4,6-trinitrophenol
—— Grevilline B —— C18H12O7
Grevilline B
—— 2-[1-Hydroxy-2-(7-phenyl-2,3,6,7-tetrahydro-1H-[1,4]diazepin-5-yl)-vinyl]-4-methoxy-phenol —— C20H22N2O3
2-[1-Hydroxy-2-(7-phenyl-2,3,6,7-tetrahydro-1H-[1,4]diazepin-5-yl)-vinyl]-4-methoxy-phenol
—— 2-(Chloro-difluoro-methyl)-3-fluoro-3-(4-hydroxy-3-methyl-phenylsulfanyl)-acrylic acid methyl ester —— C12H10ClF3O3S
2-(Chloro-difluoro-methyl)-3-fluoro-3-(4-hydroxy-3-methyl-phenylsulfanyl)-acrylic acid methyl ester
—— Grevilline D —— C18H12O8
Grevilline D
—— 4-[(1S)-2-amino-1-hydroxyethyl]-3-chlorophenol —— C8H10ClNO2
4-[(1S)-2-amino-1-hydroxyethyl]-3-chlorophenol
—— diethyl (3aS,5R,7S,8S,9R,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate —— C35H35N3O6
diethyl (3aS,5R,7S,8S,9R,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate
—— diethyl (3aS,5R,7S,8R,9S,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate —— C35H35N3O6
diethyl (3aS,5R,7S,8R,9S,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate
—— diethyl (3aS,5R,7S,8R,9R,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate —— C35H35N3O6
diethyl (3aS,5R,7S,8R,9R,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate
—— diethyl (3aS,5R,7S,8S,9S,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate —— C35H35N3O6
diethyl (3aS,5R,7S,8S,9S,9bR)-5-(4-hydroxyphenyl)-1-methyl-6-oxo-3,8-diphenyl-4,5,7,8,9,9b-hexahydro-3aH-pyrazolo[3,4-c]isoquinoline-7,9-dicarboxylate
—— Pyrimidine-2,4,6(1H,3H,5H)-trione, 5-(4-hydroxy-3-methoxybenzylidene)-1-(4-methylpentyl)- —— C18H22N2O5
Pyrimidine-2,4,6(1H,3H,5H)-trione, 5-(4-hydroxy-3-methoxybenzylidene)-1-(4-methylpentyl)-
—— N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]dodecane-1-sulfonamide —— C20H34N2O3S
N-[(Z)-1-(3-hydroxyphenyl)ethylideneamino]dodecane-1-sulfonamide
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-(1,3-thiazol-2-ylamino)ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C26H23N5O4S2
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-oxo-2-(1,3-thiazol-2-ylamino)ethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-6-[2-(4-acetamidoanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H29N5O5S
(4R)-6-[2-(4-acetamidoanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-6-[2-(4-acetamidoanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H29N5O5S
(4S)-6-[2-(4-acetamidoanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide