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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 (2E,5R)-2-[[2-[2-(benzylamino)-2-oxoethoxy]phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C33H31N3O7S
ethyl (2E,5R)-2-[[2-[2-(benzylamino)-2-oxoethoxy]phenyl]methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5R)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl (2Z,5R)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— [(2S)-1-amino-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C11H13NO4
[(2S)-1-amino-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [2-Oxo-2-[2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)ethylamino]ethyl] 2-(4-hydroxyphenyl)acetate —— C15H16N2O5S2
[2-Oxo-2-[2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)ethylamino]ethyl] 2-(4-hydroxyphenyl)acetate
—— [(2S)-1-(cyclopropylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate —— C14H17NO4
[(2S)-1-(cyclopropylamino)-1-oxopropan-2-yl] 2-(4-hydroxyphenyl)acetate
—— [2-Oxo-2-(2-phenylethylamino)ethyl] 2-(4-hydroxyphenyl)acetate —— C18H19NO4
[2-Oxo-2-(2-phenylethylamino)ethyl] 2-(4-hydroxyphenyl)acetate
—— ethyl (2Z,5S)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl (2Z,5S)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-3-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (2E,4E)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one —— C23H30N2O3
(2E,4E)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one
—— (2Z,4Z)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one —— C23H30N2O3
(2Z,4Z)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one
—— (2Z,4E)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one —— C23H30N2O3
(2Z,4E)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one
—— (2E,4Z)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one —— C23H30N2O3
(2E,4Z)-5-(dimethylamino)-1-[3-[(2Z,4Z)-5-(dimethylamino)-4-methylpenta-2,4-dienoyl]-2-hydroxy-5-methylphenyl]-4-methylpenta-2,4-dien-1-one
—— 2-methoxyethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate —— C16H19ClN2O5S
2-methoxyethyl (4R)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— (2E,5Z)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one —— C16H16ClNO3S
(2E,5Z)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one
—— (2E,5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one —— C16H16ClNO3S
(2E,5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one
—— (2Z,5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one —— C16H16ClNO3S
(2Z,5E)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-2-(3,3-dimethyl-2-oxobutylidene)-1,3-thiazolidin-4-one
—— 4-[(E)-[(5S)-5-methyl-2-morpholin-4-ylcyclohex-2-en-1-ylidene]methyl]phenol —— C18H23NO2
4-[(E)-[(5S)-5-methyl-2-morpholin-4-ylcyclohex-2-en-1-ylidene]methyl]phenol
—— 4-[(E)-[(5R)-5-methyl-2-morpholin-4-ylcyclohex-2-en-1-ylidene]methyl]phenol —— C18H23NO2
4-[(E)-[(5R)-5-methyl-2-morpholin-4-ylcyclohex-2-en-1-ylidene]methyl]phenol
—— (Z)-3-(3,6-dimethyl-1-benzofuran-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one —— C20H18O4
(Z)-3-(3,6-dimethyl-1-benzofuran-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
—— 1-[(2-Hydroxy-5-nitrophenyl)methyl]-3-(4-propan-2-ylphenyl)thiourea —— C17H19N3O3S
1-[(2-Hydroxy-5-nitrophenyl)methyl]-3-(4-propan-2-ylphenyl)thiourea
—— 1-[(2-Hydroxy-5-nitrophenyl)methyl]-3-(3-methoxyphenyl)thiourea —— C15H15N3O4S
1-[(2-Hydroxy-5-nitrophenyl)methyl]-3-(3-methoxyphenyl)thiourea
—— 1-(4-Butylphenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea —— C18H21N3O3S
1-(4-Butylphenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea
—— 1-(4-Ethylphenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea —— C16H17N3O3S
1-(4-Ethylphenyl)-3-[(2-hydroxy-5-nitrophenyl)methyl]thiourea
—— ethyl (2Z,5R)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C25H22BrN3O8S
ethyl (2Z,5R)-5-(2-bromo-4,5-dimethoxyphenyl)-2-[(2-hydroxy-5-nitrophenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(Z)-1-hydroxy-3-(2-hydroxy-3-methoxyphenyl)prop-2-enylidene]-6-methylpyran-2,4-dione —— C16H14O6
3-[(Z)-1-hydroxy-3-(2-hydroxy-3-methoxyphenyl)prop-2-enylidene]-6-methylpyran-2,4-dione
—— 4-[(4R)-2-amino-5-methyl-4H-imidazol-4-yl]phenol —— C10H11N3O
4-[(4R)-2-amino-5-methyl-4H-imidazol-4-yl]phenol
—— 4-[(4S)-2-amino-5-methyl-4H-imidazol-4-yl]phenol —— C10H11N3O
4-[(4S)-2-amino-5-methyl-4H-imidazol-4-yl]phenol
—— (4E)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-2-(4-nitrophenyl)pyrazol-3-one —— C24H19N3O6
(4E)-4-[(3-hydroxy-4-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-2-(4-nitrophenyl)pyrazol-3-one
—— methyl (4E)-4-[(3-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-prop-2-enylpyrrole-3-carboxylate —— C17H17NO4
methyl (4E)-4-[(3-hydroxyphenyl)methylidene]-2-methyl-5-oxo-1-prop-2-enylpyrrole-3-carboxylate
—— (5E)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxo-1-propylpyridine-3-carbonitrile —— C18H19N3O3
(5E)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxo-1-propylpyridine-3-carbonitrile
—— (5E)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxo-1-[[(2R)-oxolan-2-yl]methyl]pyridine-3-carbonitrile —— C20H21N3O4
(5E)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxo-1-[[(2R)-oxolan-2-yl]methyl]pyridine-3-carbonitrile
—— (4Z)-2-[(3R)-1,1-dioxothiolan-3-yl]-4-[(2-hydroxy-5-methylanilino)methylidene]-5-methylpyrazol-3-one —— C16H19N3O4S
(4Z)-2-[(3R)-1,1-dioxothiolan-3-yl]-4-[(2-hydroxy-5-methylanilino)methylidene]-5-methylpyrazol-3-one
—— ethyl (2E,5R)-5-(3,4-diethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl (2E,5R)-5-(3,4-diethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(3,4-diethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl (2E,5S)-5-(3,4-diethoxyphenyl)-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxo-1-[[(2S)-oxolan-2-yl]methyl]pyridine-3-carbonitrile —— C20H21N3O4
(5E)-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxo-1-[[(2S)-oxolan-2-yl]methyl]pyridine-3-carbonitrile
—— (4Z)-2-[(3S)-1,1-dioxothiolan-3-yl]-4-[(2-hydroxy-5-methylanilino)methylidene]-5-methylpyrazol-3-one —— C16H19N3O4S
(4Z)-2-[(3S)-1,1-dioxothiolan-3-yl]-4-[(2-hydroxy-5-methylanilino)methylidene]-5-methylpyrazol-3-one
—— ethyl (2E,5R)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl (2E,5R)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(3,4-diethoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C28H30N2O7S
ethyl (2E,5S)-5-(3,4-diethoxyphenyl)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H27BrN2O6S
ethyl (2E,5R)-2-[(2-bromo-4-hydroxy-5-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H28N2O6S
ethyl (2E,5S)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-7-methyl-3-oxo-5-(2-propan-2-yloxyphenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-1-[(3R)-1,1-dioxothiolan-3-yl]-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C19H19N3O5S
(5E)-1-[(3R)-1,1-dioxothiolan-3-yl]-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— (5E)-1-[(3S)-1,1-dioxothiolan-3-yl]-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile —— C19H19N3O5S
(5E)-1-[(3S)-1,1-dioxothiolan-3-yl]-5-[(4-hydroxy-2-methylanilino)methylidene]-4-methyl-2,6-dioxopyridine-3-carbonitrile
—— ethyl (2E,5R)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5R)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H30N2O7S
ethyl (2E,5S)-5-(3-ethoxy-4-prop-2-enoxyphenyl)-2-[(2-hydroxy-3-methoxyphenyl)methylidene]-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2,5-dimethylfuran-3-carboxamide —— C15H15BrN2O4
N-[(Z)-(2-bromo-5-hydroxy-4-methoxyphenyl)methylideneamino]-2,5-dimethylfuran-3-carboxamide
—— (3Z)-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]-1-(2-phenylethyl)pyrrolidine-2,5-dione —— C20H19NO5
(3Z)-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]-1-(2-phenylethyl)pyrrolidine-2,5-dione
—— (3Z)-1-(1,3-benzodioxol-5-yl)-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]pyrrolidine-2,5-dione —— C19H15NO7
(3Z)-1-(1,3-benzodioxol-5-yl)-3-[(3,4-dihydroxy-5-methoxyphenyl)methylidene]pyrrolidine-2,5-dione
—— (5E)-2-amino-5-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]-1,3-thiazol-4-one —— C14H9N3O5S
(5E)-2-amino-5-[[5-(2-hydroxy-5-nitrophenyl)furan-2-yl]methylidene]-1,3-thiazol-4-one
—— N-[(1R)-1-(1-adamantyl)ethyl]-3-(2-hydroxyphenyl)propanamide —— C21H29NO2
N-[(1R)-1-(1-adamantyl)ethyl]-3-(2-hydroxyphenyl)propanamide
—— (5Z)-3-[(4-chlorophenyl)methyl]-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one —— C17H11ClN2O4S2
(5Z)-3-[(4-chlorophenyl)methyl]-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— (1R,9S,13E,16S)-16-acetyl-13-[(2-hydroxy-3-methoxyphenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one —— C23H20N2O5S
(1R,9S,13E,16S)-16-acetyl-13-[(2-hydroxy-3-methoxyphenyl)methylidene]-9-methyl-8-oxa-12-thia-10,15-diazatetracyclo[7.6.1.02,7.011,15]hexadeca-2,4,6,10-tetraen-14-one