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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-[[4-[(3-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C20H27BrN2O3+2
4-[[4-[(3-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— Cyclopentyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]azanium —— C14H22NO3+
Cyclopentyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]azanium
—— methyl (2S)-2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate —— C10H9F3O5
methyl (2S)-2-(3,4-dihydroxyphenyl)-3,3,3-trifluoro-2-hydroxypropanoate
—— 2-(3-Bromo-4-hydroxy-5-methoxyphenyl)acetate —— C9H8BrO4-
2-(3-Bromo-4-hydroxy-5-methoxyphenyl)acetate
—— 2-(4-Hydroxy-3,5-dimethoxyphenyl)ethylazanium —— C10H16NO3+
2-(4-Hydroxy-3,5-dimethoxyphenyl)ethylazanium
—— (2R,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
(2R,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
—— (4R)-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-6-propylsulfanyl-3,4-dihydro-1H-pyridine-5-carbonitrile —— C16H18N2O3S
(4R)-4-(4-hydroxy-3-methoxyphenyl)-2-oxo-6-propylsulfanyl-3,4-dihydro-1H-pyridine-5-carbonitrile
—— N'-[(E)-1-(benzotriazol-1-yl)prop-1-en-2-yl]-4-hydroxy-3-methoxybenzohydrazide —— C17H17N5O3
N'-[(E)-1-(benzotriazol-1-yl)prop-1-en-2-yl]-4-hydroxy-3-methoxybenzohydrazide
—— (2R)-2-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate —— C15H14NO5S2-
(2R)-2-[5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoate
—— (11R,14Z)-11-(4-chlorophenyl)-14-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one —— C27H17ClN4O6S
(11R,14Z)-11-(4-chlorophenyl)-14-[(4-hydroxy-3,5-dinitrophenyl)methylidene]-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one
—— (5E)-2-(4-benzylpiperazin-4-ium-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one —— C22H24N3O3S+
(5E)-2-(4-benzylpiperazin-4-ium-1-yl)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one
—— 4-(6,6-Dimethyl-5,7-dinitro-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl)-2-methoxyphenol —— C17H24N4O6+2
4-(6,6-Dimethyl-5,7-dinitro-1,3-diazoniatricyclo[3.3.1.13,7]decan-2-yl)-2-methoxyphenol
—— 2-[(6R)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-4-nitrophenol —— C20H14N4O3
2-[(6R)-6,12-dihydrobenzimidazolo[1,2-c]quinazolin-6-yl]-4-nitrophenol
—— 2-[[4-[(4-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol —— C19H25BrN2O2+2
2-[[4-[(4-Bromophenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-4-methoxyphenol
—— (5Z)-5-(5-bromo-2-hydroxybenzylidene)-3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one —— C13H10BrNO2S2
(5Z)-5-(5-bromo-2-hydroxybenzylidene)-3-(prop-2-en-1-yl)-2-thioxo-1,3-thiazolidin-4-one
—— (2S)-2-(2-hydroxy-3-methoxyphenyl)-6-(3-methoxyanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile —— C19H17N3O4S
(2S)-2-(2-hydroxy-3-methoxyphenyl)-6-(3-methoxyanilino)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
—— (3E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]oxan-4-one —— C21H20O6
(3E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]oxan-4-one
—— (2S,4S)-3-acetyl-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-1,3-thiazolidine-4-carboxylate —— C13H13BrNO5S-
(2S,4S)-3-acetyl-2-(3-bromo-4-hydroxy-5-methoxyphenyl)-1,3-thiazolidine-4-carboxylate
—— Benzyl-[2-(dimethylazaniumyl)ethyl]-[(2-hydroxy-3-methoxyphenyl)methyl]azanium —— C19H28N2O2+2
Benzyl-[2-(dimethylazaniumyl)ethyl]-[(2-hydroxy-3-methoxyphenyl)methyl]azanium
—— methyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-2-methyl-5-oxo-3,4-dihydroindeno[1,2-b]pyridine-3-carboxylate —— C22H18ClNO5
methyl (4S)-4-(3-chloro-4-hydroxy-5-methoxyphenyl)-2-methyl-5-oxo-3,4-dihydroindeno[1,2-b]pyridine-3-carboxylate
—— 3-[(7S)-7-(4-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C18H19NO5S
3-[(7S)-7-(4-hydroxy-3-methoxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 3-[(7S)-7-(5-bromo-2-hydroxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione —— C17H16BrNO4S
3-[(7S)-7-(5-bromo-2-hydroxyphenyl)-1,4-thiazepan-5-ylidene]-6-methylpyran-2,4-dione
—— 4-[[4-[(3-Ethoxy-4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol —— C23H34N2O5+2
4-[[4-[(3-Ethoxy-4-methoxyphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]-2,6-dimethoxyphenol
—— 4-[(4-Benzylpiperazine-1,4-diium-1-yl)methyl]-2-bromo-6-methoxyphenol —— C19H25BrN2O2+2
4-[(4-Benzylpiperazine-1,4-diium-1-yl)methyl]-2-bromo-6-methoxyphenol
—— (5,5-Diethyl-4,6-dioxo-1,3-diazinan-2-ylidene)-[2-(4-hydroxyphenyl)ethyl]azanium —— C16H22N3O3+
(5,5-Diethyl-4,6-dioxo-1,3-diazinan-2-ylidene)-[2-(4-hydroxyphenyl)ethyl]azanium
—— (2R)-2-hydroxy-2-(3-hydroxy-4-methoxyphenyl)acetate —— C9H9O5-
(2R)-2-hydroxy-2-(3-hydroxy-4-methoxyphenyl)acetate
—— 2-(2-Hydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol —— C16H24N2O2+2
2-(2-Hydroxyphenyl)-5,7-dimethyl-1,3-diazoniatricyclo[3.3.1.13,7]decan-6-ol
—— 4-[(2S)-5-benzyl-2,3-dihydro-1,3,4-thiadiazol-2-yl]benzene-1,3-diol —— C15H14N2O2S
4-[(2S)-5-benzyl-2,3-dihydro-1,3,4-thiadiazol-2-yl]benzene-1,3-diol
—— 2-Methoxy-4-(morpholin-4-ium-4-ylmethyl)phenol —— C12H18NO3+
2-Methoxy-4-(morpholin-4-ium-4-ylmethyl)phenol
—— 4-Methoxy-2-[[4-[(4-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol —— C20H28N2O2+2
4-Methoxy-2-[[4-[(4-methylphenyl)methyl]piperazine-1,4-diium-1-yl]methyl]phenol
—— 4-(Carboxymethyl)-2-fluorophenolate —— C8H6FO3-
4-(Carboxymethyl)-2-fluorophenolate
—— 4-[(3R)-3-(benzylamino)butyl]-2-methoxyphenol —— C18H23NO2
4-[(3R)-3-(benzylamino)butyl]-2-methoxyphenol
—— [(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]azanium —— C8H12NO2+
[(2R)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]azanium
—— [(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-methylazanium —— C9H14NO2+
[(2S)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]-methylazanium
—— 2-[(1S)-1-(2-aminophenyl)sulfanyl-2-nitroethyl]-6-methoxyphenol —— C15H16N2O4S
2-[(1S)-1-(2-aminophenyl)sulfanyl-2-nitroethyl]-6-methoxyphenol
—— [(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]azanium —— C9H14NO3+
[(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]azanium
—— (2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethanaminium —— C9H14NO3+
(2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethanaminium
—— 2-(3,4-dihydroxyphenyl)ethyl-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]azanium —— C18H24NO3+
2-(3,4-dihydroxyphenyl)ethyl-[(2S)-4-(4-hydroxyphenyl)butan-2-yl]azanium
—— (2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethanaminium —— C8H12NO3+
(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethanaminium
—— ethyl (Z)-3-[(3R)-3-(5-chloro-2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]but-2-enoate —— C19H19ClN2O3S
ethyl (Z)-3-[(3R)-3-(5-chloro-2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]but-2-enoate
—— (E)-4-[(3S)-5-(2-chlorophenyl)-3-(2-hydroxy-5-methylphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C20H17ClN2O4
(E)-4-[(3S)-5-(2-chlorophenyl)-3-(2-hydroxy-5-methylphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— ethyl (Z)-3-[(3R)-3-(5-chloro-2-hydroxyphenyl)-5-(4-fluorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate —— C21H20ClFN2O3
ethyl (Z)-3-[(3R)-3-(5-chloro-2-hydroxyphenyl)-5-(4-fluorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate
—— ethyl (Z)-3-[(3S)-3-(5-chloro-2-hydroxyphenyl)-5-(4-fluorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate —— C21H20ClFN2O3
ethyl (Z)-3-[(3S)-3-(5-chloro-2-hydroxyphenyl)-5-(4-fluorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate
—— ethyl (Z)-3-[(3R)-3-(5-chloro-2-hydroxyphenyl)-5-(4-chlorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate —— C21H20Cl2N2O3
ethyl (Z)-3-[(3R)-3-(5-chloro-2-hydroxyphenyl)-5-(4-chlorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate
—— ethyl (Z)-3-[(3S)-3-(5-chloro-2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]but-2-enoate —— C19H19ClN2O3S
ethyl (Z)-3-[(3S)-3-(5-chloro-2-hydroxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazol-2-yl]but-2-enoate
—— (Z)-4-[(3S)-3-(2-hydroxyphenyl)-5-(5-methylfuran-2-yl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C18H16N2O5
(Z)-4-[(3S)-3-(2-hydroxyphenyl)-5-(5-methylfuran-2-yl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (Z)-4-[(3R)-3-(2-hydroxyphenyl)-5-(5-methylfuran-2-yl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C18H16N2O5
(Z)-4-[(3R)-3-(2-hydroxyphenyl)-5-(5-methylfuran-2-yl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (E)-4-[(3S)-3-(2-hydroxyphenyl)-5-pyridin-3-yl-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C18H15N3O4
(E)-4-[(3S)-3-(2-hydroxyphenyl)-5-pyridin-3-yl-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— (Z)-4-[(3R)-5-(1,3-benzodioxol-5-yl)-3-(2-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid —— C21H18N2O7
(Z)-4-[(3R)-5-(1,3-benzodioxol-5-yl)-3-(2-hydroxy-3-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-4-oxobut-2-enoic acid
—— ethyl (Z)-3-[(3S)-3-(5-chloro-2-hydroxyphenyl)-5-(4-chlorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate —— C21H20Cl2N2O3
ethyl (Z)-3-[(3S)-3-(5-chloro-2-hydroxyphenyl)-5-(4-chlorophenyl)-3,4-dihydropyrazol-2-yl]but-2-enoate