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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
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-(2-methyl-4-nitroanilino)-2-oxoethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H27N5O6S
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-6-[2-(2-methyl-4-nitroanilino)-2-oxoethyl]sulfanyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(4-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O5S
(4R)-5-cyano-6-[2-(4-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(4-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H28N4O5S
(4S)-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-[2-(4-methoxyanilino)-2-oxoethyl]sulfanyl-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(4-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H25FN4O4S
(4S)-5-cyano-6-[2-(4-fluoroanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-6-[2-(3-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H27ClN4O4S
(4S)-6-[2-(3-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(4-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O5S
(4S)-5-cyano-6-[2-(4-ethoxyanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2,6-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4S)-5-cyano-6-[2-(2,6-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(3,4-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4S)-5-cyano-6-[2-(3,4-dimethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-6-(2-anilino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C29H26N4O4S
(4S)-6-(2-anilino-2-oxoethyl)sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-6-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H25N5O4S2
(4R)-6-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-5-cyano-6-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4S)-5-cyano-6-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4R)-5-cyano-6-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C31H30N4O4S
(4R)-5-cyano-6-[2-(2-ethylanilino)-2-oxoethyl]sulfanyl-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (4S)-6-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide —— C30H25N5O4S2
(4S)-6-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-N-phenyl-1,4-dihydropyridine-3-carboxamide
—— (8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-2-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C22H19BrClN3O3S
(8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-2-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(4-butylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C25H26BrN3O3S
(8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(4-butylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-2-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C22H19BrClN3O3S
(8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-2-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-4-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C22H19BrClN3O3S
(8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-4-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2,4-dimethoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C23H22BrN3O5S
(8S)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2,4-dimethoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2,4-dimethoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C23H22BrN3O5S
(8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2,4-dimethoxyphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-4-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C22H19BrClN3O3S
(8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(3-chloro-4-methylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— (8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(4-butylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile —— C25H26BrN3O3S
(8R)-8-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(4-butylphenyl)-6-oxo-2,4,7,8-tetrahydropyrido[2,1-b][1,3,5]thiadiazine-9-carbonitrile
—— [(Z)-2-(3,4-dihydroxyphenyl)ethenyl] hydrogen sulfate —— C8H8O6S
[(Z)-2-(3,4-dihydroxyphenyl)ethenyl] hydrogen sulfate
—— (Z)-narain —— C3H9N3*C8H8O6S
(Z)-narain
—— (2E,5S)-5-(4-hydroxy-3-methoxyphenyl)-2-[(4-methoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C29H25N3O5S
(2E,5S)-5-(4-hydroxy-3-methoxyphenyl)-2-[(4-methoxyphenyl)methylidene]-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 2-((1S,2R)-2-Dipropylamino-cyclopropyl)-4-fluoro-phenol —— C15H22FNO
2-((1S,2R)-2-Dipropylamino-cyclopropyl)-4-fluoro-phenol
—— ethyl (2Z,5R)-2-[[5-bromo-2-(cyanomethoxy)phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H21BrClN3O6S
ethyl (2Z,5R)-2-[[5-bromo-2-(cyanomethoxy)phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2Z,5S)-2-[[5-bromo-2-(cyanomethoxy)phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C26H21BrClN3O6S
ethyl (2Z,5S)-2-[[5-bromo-2-(cyanomethoxy)phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-Methoxy-4-methyl-2-(3-methyl-but-2-enyl)-phenol —— C13H18O2
3-Methoxy-4-methyl-2-(3-methyl-but-2-enyl)-phenol
—— 2-Hydroxy-3-methyl-4,5-dinitrobenzenediazonium —— C7H5N4O5+
2-Hydroxy-3-methyl-4,5-dinitrobenzenediazonium
—— (1S,10R,11R)-11-methyl-12,13-dioxatricyclo[8.2.1.02,7]trideca-2(7),3,5,8-tetraen-3-ol —— C12H12O3
(1S,10R,11R)-11-methyl-12,13-dioxatricyclo[8.2.1.02,7]trideca-2(7),3,5,8-tetraen-3-ol
—— (2E)-N-[2-[3,5-dibromo-4-[3-[[(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]-2-hydroxypropoxy]phenyl]ethyl]-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanamide —— C31H30Br6N4O10
(2E)-N-[2-[3,5-dibromo-4-[3-[[(2E)-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoyl]amino]-2-hydroxypropoxy]phenyl]ethyl]-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanamide
—— (5E)-5-[(3,4-dihydroxyphenyl)methylidene]-3-[2-(4-hydroxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one —— C18H15NO4S2
(5E)-5-[(3,4-dihydroxyphenyl)methylidene]-3-[2-(4-hydroxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 36,42,48,53-Tetratert-butyl-3,6,29,32-tetraoxa-14,21-diazanonacyclo[32.15.7.140,44.151,55.02,46.07,12.015,20.023,28.033,38]octapentaconta-1,7,9,11,13,15,17,19,21,23,25,27,33,35,37,40(58),41,43,46,48,51,53,55(57)-tricosaene-57,58-diol —— C68H76N2O6
36,42,48,53-Tetratert-butyl-3,6,29,32-tetraoxa-14,21-diazanonacyclo[32.15.7.140,44.151,55.02,46.07,12.015,20.023,28.033,38]octapentaconta-1,7,9,11,13,15,17,19,21,23,25,27,33,35,37,40(58),41,43,46,48,51,53,55(57)-tricosaene-57,58-diol
—— [11,23-Ditert-butyl-25,26,27,28-tetrahydroxy-17-[(trimethylazaniumyl)methyl]-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]methyl-trimethylazanium;diiodide —— C44H60I2N2O4
[11,23-Ditert-butyl-25,26,27,28-tetrahydroxy-17-[(trimethylazaniumyl)methyl]-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]methyl-trimethylazanium;diiodide
—— (5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H10BrNO3S2
(5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-(3,5-Dibromo-2-hydroxy-4-methoxy-phenyl)-N-[2-(3,5-dibromo-4-hydroxy-phenyl)-ethyl]-2-[(Z)-hydroxyimino]-propionamide —— C18H16Br4N2O5
3-(3,5-Dibromo-2-hydroxy-4-methoxy-phenyl)-N-[2-(3,5-dibromo-4-hydroxy-phenyl)-ethyl]-2-[(Z)-hydroxyimino]-propionamide
—— (5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-[(2-chloro-4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione —— C17H10BrClFNO3S
(5E)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-[(2-chloro-4-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione
—— ethyl (2E,5R)-5-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C20H20N2O7S
ethyl (2E,5R)-5-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— ethyl (2E,5S)-5-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C20H20N2O7S
ethyl (2E,5S)-5-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5E)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one —— C12H10BrClN2O2S
(5E)-5-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one
—— 4-[(3E)-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[2-(4-oxocyclohexa-2,5-dien-1-ylidene)ethylidene]-1H-pyrazol-2-yl]benzoic acid —— C27H22N2O5
4-[(3E)-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3-[2-(4-oxocyclohexa-2,5-dien-1-ylidene)ethylidene]-1H-pyrazol-2-yl]benzoic acid
—— 3-Bromo-5-(5-tert-butyl-1,1,3,3-tetraoxo-1,3-dithian-2-yl)-4-hydroxybenzenediazonium —— C14H18BrN2O5S2+
3-Bromo-5-(5-tert-butyl-1,1,3,3-tetraoxo-1,3-dithian-2-yl)-4-hydroxybenzenediazonium
—— 2-Bromo-6-(5-tert-butyl-1,3-dithian-2-yl)-4-nitrophenol —— C14H18BrNO3S2
2-Bromo-6-(5-tert-butyl-1,3-dithian-2-yl)-4-nitrophenol
—— 2-[2-(3-Hydroxy-4-methoxyphenyl)pyrimidin-4-yl]-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one —— C18H16N4O3
2-[2-(3-Hydroxy-4-methoxyphenyl)pyrimidin-4-yl]-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one
—— 5-Hydroxy-2-pyridin-2-yl-1,2-benzoselenazol-3-one —— C12H8N2O2Se
5-Hydroxy-2-pyridin-2-yl-1,2-benzoselenazol-3-one
—— 2,4-Bis-imidazol-1-ylmethyl-6-methoxy-phenol —— C15H16N4O2
2,4-Bis-imidazol-1-ylmethyl-6-methoxy-phenol
—— 4-[2-(Cyclopentylamino)-1-hydroxyethyl]benzene-1,2-diol;hydrochloride —— C13H20ClNO3
4-[2-(Cyclopentylamino)-1-hydroxyethyl]benzene-1,2-diol;hydrochloride
—— 2-[2-[5-(4-Hydroxyphenyl)thiophen-2-yl]-1,1-dioxothian-2-yl]acetic acid —— C17H18O5S2
2-[2-[5-(4-Hydroxyphenyl)thiophen-2-yl]-1,1-dioxothian-2-yl]acetic acid
—— O-[(4-tert-butylphenyl)methyl] N-[(4-hydroxy-3-methoxyphenyl)methyl]carbamothioate —— C20H25NO3S
O-[(4-tert-butylphenyl)methyl] N-[(4-hydroxy-3-methoxyphenyl)methyl]carbamothioate
—— 2-(2-Hydroxy-5-nonylphenyl)ethyl hydrogen sulfate —— C17H28O5S
2-(2-Hydroxy-5-nonylphenyl)ethyl hydrogen sulfate