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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
—— ethyl (2Z)-2-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H17BrCl2N2O4S
ethyl (2Z)-2-[(5-bromo-3-chloro-2-hydroxyphenyl)methylidene]-5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-amino-3,5,6-trichloro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-2-carboxamide —— C14H11Cl3N4O3
4-amino-3,5,6-trichloro-N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]pyridine-2-carboxamide
—— (5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C18H13BrFNO4S
(5Z)-5-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-3-[(4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— O-Methylnoradrenalin —— C9H13NO3
O-Methylnoradrenalin
—— 5-[(1S)-2-amino-1-hydroxyethyl]-3-chlorobenzene-1,2-diol —— C8H10ClNO3
5-[(1S)-2-amino-1-hydroxyethyl]-3-chlorobenzene-1,2-diol
—— (6E)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one —— C13H9N3O6
(6E)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-nitrocyclohexa-2,4-dien-1-one
—— ethyl (5Z)-2-(4-chloroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H18ClNO5S
ethyl (5Z)-2-(4-chloroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— (5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(4-fluorophenyl)imino-1,3-thiazolidin-4-one —— C16H10BrFN2O2S
(5E)-5-[(5-bromo-2-hydroxyphenyl)methylidene]-2-(4-fluorophenyl)imino-1,3-thiazolidin-4-one
—— (5E)-5-{[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene}-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile —— C18H11N3O6
(5E)-5-{[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene}-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino]-2-phenylimidazol-4-one —— C25H21N3O5
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-[[(E)-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino]-2-phenylimidazol-4-one
—— 1,3-Diethyl-5-[(2-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione —— C17H20N2O5S
1,3-Diethyl-5-[(2-hydroxy-3,5-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
—— ethyl (2Z)-5-(4-fluorophenyl)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H18FN3O6S
ethyl (2Z)-5-(4-fluorophenyl)-2-(2-hydroxy-3-nitrobenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-5-(2,3-dihydroxybenzylidene)-2-sulfanyl-1,3-thiazol-4(5H)-one —— C10H7NO3S2
(5Z)-5-(2,3-dihydroxybenzylidene)-2-sulfanyl-1,3-thiazol-4(5H)-one
—— ethyl (2Z)-5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2Z)-5-(2,4-dimethoxyphenyl)-2-[(4-hydroxy-3-methoxy-5-prop-2-enylphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (4E)-1-(3,4-dimethylphenyl)-4-(2-hydroxy-3-methylbenzylidene)pyrazolidine-3,5-dione —— C19H18N2O3
(4E)-1-(3,4-dimethylphenyl)-4-(2-hydroxy-3-methylbenzylidene)pyrazolidine-3,5-dione
—— 5-(2,4-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester —— C25H23N3O8S
5-(2,4-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester
—— ethyl (5Z)-2-(2,4-dichloroanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate —— C21H17Cl2NO5S
ethyl (5Z)-2-(2,4-dichloroanilino)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-4-oxothiophene-3-carboxylate
—— 3-(4-Ethylphenyl)-2-[(4-ethylphenyl)imino]-5-(4-hydroxybenzylidene)-1,3-thiazolidin-4-one —— C26H24N2O2S
3-(4-Ethylphenyl)-2-[(4-ethylphenyl)imino]-5-(4-hydroxybenzylidene)-1,3-thiazolidin-4-one
—— (Z)-5-((E)-3-(furan-2-yl)allylidene)-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one —— C16H11NO3S2
(Z)-5-((E)-3-(furan-2-yl)allylidene)-3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one
—— (4S)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18ClN3O3S
(4S)-1-(3-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-one —— C16H19N3O3S
(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-one
—— (4S)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H16N4O3S
(4S)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C21H18N4O3S
(4R)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— (4R)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H16N4O3S
(4R)-1-(1,3-benzothiazol-2-yl)-4-(3-hydroxy-4-methoxyphenyl)-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— 2-methoxy-4-[[(2S)-2-(5-methyl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol —— C16H20N2O3
2-methoxy-4-[[(2S)-2-(5-methyl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol
—— 2-[[(2R)-2-(5-ethyl-3-methyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-5-methoxyphenol —— C18H24N2O3
2-[[(2R)-2-(5-ethyl-3-methyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-5-methoxyphenol
—— 2-[[(2S)-2-(3,5-dimethyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-6-methoxyphenol —— C17H22N2O3
2-[[(2S)-2-(3,5-dimethyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-6-methoxyphenol
—— 2-methoxy-6-[[(2R)-2-(5-methyl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol —— C16H20N2O3
2-methoxy-6-[[(2R)-2-(5-methyl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol
—— 2-methoxy-6-[[(2R)-2-(5-propan-2-yl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
2-methoxy-6-[[(2R)-2-(5-propan-2-yl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol
—— 2-methoxy-5-[[(2S)-2-(5-propan-2-yl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
2-methoxy-5-[[(2S)-2-(5-propan-2-yl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol
—— 5-methoxy-2-[[(2R)-2-(5-propan-2-yl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol —— C18H24N2O3
5-methoxy-2-[[(2R)-2-(5-propan-2-yl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenol
—— 5-[[(2R)-2-(3,5-dimethyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-2-methoxyphenol —— C17H22N2O3
5-[[(2R)-2-(3,5-dimethyl-1,2-oxazol-4-yl)pyrrolidin-1-yl]methyl]-2-methoxyphenol
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-4-oxo-5-(thiophen-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]acetamide —— C18H16N2O4S3
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-4-oxo-5-(thiophen-2-ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5Z)-5-[(2-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide —— C21H19FN2O5S
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-[(5Z)-5-[(2-fluorophenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]propanamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(2-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide —— C21H20N2O6S
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5Z)-5-(2-methoxybenzylidene)-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-[(3-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide —— C21H19FN2O4S2
N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[(5E)-5-[(3-fluorophenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanamide
—— 2-[[(R)-(2-fluorophenyl)-(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]amino]-4-methylphenol —— C22H18FN3O2
2-[[(R)-(2-fluorophenyl)-(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]amino]-4-methylphenol
—— 5-[(E)-2-(1H-benzimidazol-2-yl)-2-(1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol —— C23H17N3O2S
5-[(E)-2-(1H-benzimidazol-2-yl)-2-(1,3-benzothiazol-2-yl)ethenyl]-2-methoxyphenol
—— (E)-2-(4-bromophenyl)sulfonyl-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile —— C16H12BrNO4S
(E)-2-(4-bromophenyl)sulfonyl-3-(3-hydroxy-4-methoxyphenyl)prop-2-enenitrile
—— (4S)-1-(2-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H18ClN3O3S
(4S)-1-(2-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4S)-1-(3-chloro-4-methylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H20ClN3O3S
(4S)-1-(3-chloro-4-methylphenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C20H21N5O3S
(4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4-ethylphenyl)-4-(3-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one —— C21H21N3O2S
(4R)-1-(4-ethylphenyl)-4-(3-hydroxyphenyl)-3-methyl-2,4-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one
—— (4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C20H21N5O3
(4R)-1-(4,6-dimethylpyrimidin-2-yl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylmethoxybenzamide —— C22H20N2O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-2-phenylmethoxybenzamide
—— (4S)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one —— C22H20N4O4S
(4S)-1-(1,3-benzothiazol-2-yl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-methyl-4,5-dihydro-2H-pyrazolo[3,4-b]pyridin-6-one
—— N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-(3-methylbutoxy)benzamide —— C20H24N2O4
N-[(Z)-(3-hydroxy-4-methoxyphenyl)methylideneamino]-4-(3-methylbutoxy)benzamide
—— 3-[(E)-N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate —— C16H18N8O3
3-[(E)-N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-propan-2-yltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate
—— (3E)-3-[7-(5-bromo-2-hydroxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C17H16BrNO4S
(3E)-3-[7-(5-bromo-2-hydroxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 3-[(E)-N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-thiophen-2-yltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate —— C17H14N8O3S
3-[(E)-N-[[1-(4-azaniumyl-1,2,5-oxadiazol-3-yl)-5-thiophen-2-yltriazole-4-carbonyl]amino]-C-methylcarbonimidoyl]phenolate