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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
—— (5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one —— C18H16N2O3S
(5E)-5-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-(3-methylphenyl)imino-1,3-thiazolidin-4-one
—— 1-[(3,4-Dihydroxyphenyl)methyl]-3-(2-ethylhexoxy)urea —— C16H26N2O4
1-[(3,4-Dihydroxyphenyl)methyl]-3-(2-ethylhexoxy)urea
—— 4-(2,3-Dimethoxypropyl)phenol —— C11H16O3
4-(2,3-Dimethoxypropyl)phenol
—— (E)-4-(4-hydroxy-3-nitrophenyl)-4-oxobut-2-enoic acid —— C10H7NO6
(E)-4-(4-hydroxy-3-nitrophenyl)-4-oxobut-2-enoic acid
—— 2-[3-(2-Aminoethylamino)-2-[(2-aminoethylamino)methyl]propyl]-4-bromophenol;tetrahydrochloride —— C14H29BrCl4N4O
2-[3-(2-Aminoethylamino)-2-[(2-aminoethylamino)methyl]propyl]-4-bromophenol;tetrahydrochloride
—— azanide;dichloroplatinum(2+);4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol —— C9H17Cl2N3O3Pt
azanide;dichloroplatinum(2+);4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
—— 2-(4-hydroxyphenyl)ethyl 6-[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethylamino]hexanoate 156388-73-7 C22H28Cl2N2O4
2-(4-hydroxyphenyl)ethyl 6-[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethylamino]hexanoate
—— 4-[4-[4-(dimethylamino)phenyl]-5-(2-phenylethyl)-2,3-dihydro-1H-imidazol-2-yl]-2,6-dimethoxyphenol —— C27H31N3O3
4-[4-[4-(dimethylamino)phenyl]-5-(2-phenylethyl)-2,3-dihydro-1H-imidazol-2-yl]-2,6-dimethoxyphenol
—— N-(4-hydroxyphenyl)acetamide;1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol —— C23H34N2O5
N-(4-hydroxyphenyl)acetamide;1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol
—— 9-(5-Bromo-2-hydroxyphenyl)-5,12-dioxa-2-azatricyclo[8.4.0.03,8]tetradeca-1(10),3(8)-diene-7,11-dione —— C17H14BrNO5
9-(5-Bromo-2-hydroxyphenyl)-5,12-dioxa-2-azatricyclo[8.4.0.03,8]tetradeca-1(10),3(8)-diene-7,11-dione
—— 8-(2,3-dihydroxyphenyl)-5-phenyl-2-methyl-8H-[1,2,4]triazolo[3,4-c][1,4]thiazin-3(2H)-one —— C18H15N3O3S
8-(2,3-dihydroxyphenyl)-5-phenyl-2-methyl-8H-[1,2,4]triazolo[3,4-c][1,4]thiazin-3(2H)-one
—— (cis)-4-(4-Methoxy-3-hydroxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1one —— C20H24N2O3
(cis)-4-(4-Methoxy-3-hydroxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydro-2H-phthalazin-1one
—— 2-(2-Hexyloctyl)benzene-1,4-diol —— C20H34O2
2-(2-Hexyloctyl)benzene-1,4-diol
—— 4-[2-Dimethoxyphosphoryl-1-(pyridin-3-ylamino)ethyl]-2,6-dimethylphenol —— C17H23N2O4P
4-[2-Dimethoxyphosphoryl-1-(pyridin-3-ylamino)ethyl]-2,6-dimethylphenol
—— 3-[(7E,9Z,11Z)-14-methylpentadeca-7,9,11-trienyl]benzene-1,2-diol —— C22H32O2
3-[(7E,9Z,11Z)-14-methylpentadeca-7,9,11-trienyl]benzene-1,2-diol
—— 1-adamantyl-3-hydroxy-4-(3,4-dihydroxyphenyl)-butan-1-one 791113-22-9 C20H26O4
1-adamantyl-3-hydroxy-4-(3,4-dihydroxyphenyl)-butan-1-one
—— methyl (2E,5S)-2-[[3-bromo-5-ethoxy-4-[2-(4-methylanilino)-2-oxoethoxy]phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C34H31BrClN3O8S
methyl (2E,5S)-2-[[3-bromo-5-ethoxy-4-[2-(4-methylanilino)-2-oxoethoxy]phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (2E,5R)-2-[[3-bromo-5-ethoxy-4-[2-(4-methylanilino)-2-oxoethoxy]phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C34H31BrClN3O8S
methyl (2E,5R)-2-[[3-bromo-5-ethoxy-4-[2-(4-methylanilino)-2-oxoethoxy]phenyl]methylidene]-5-(3-chloro-4-hydroxy-5-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (E,E)-2-acetaminocarbonyl-3-(3,4-dihydroxystyryl)acrylonitrile 368836-89-9 C12H10N2O3
(E,E)-2-acetaminocarbonyl-3-(3,4-dihydroxystyryl)acrylonitrile
—— (3S)-3-[(4-hydroxyphenyl)methyl]-1,4-dioxane-2,5-dione —— C11H10O5
(3S)-3-[(4-hydroxyphenyl)methyl]-1,4-dioxane-2,5-dione
—— 4-(2-Ethoxy-3-propan-2-yloxypropyl)phenol —— C14H22O3
4-(2-Ethoxy-3-propan-2-yloxypropyl)phenol
—— (3R)-3-[(4-hydroxyphenyl)methyl]-1,4-dioxane-2,5-dione —— C11H10O5
(3R)-3-[(4-hydroxyphenyl)methyl]-1,4-dioxane-2,5-dione
—— 2-(4-Hydroxyphenyl)ethanesulfinic acid —— C8H10O3S
2-(4-Hydroxyphenyl)ethanesulfinic acid
—— 4-methyl-2-[(1S,5S,6R)-6-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-yl]phenol —— C13H16O3
4-methyl-2-[(1S,5S,6R)-6-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-yl]phenol
—— ethyl (2Z,5R)-2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C21H16BrClN2O4S2
ethyl (2Z,5R)-2-[(3-bromo-5-chloro-2-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-thiophen-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3-[(Z)-6-(3-hydroxyphenyl)hex-3-en-1,5-diynyl]phenol —— C18H12O2
3-[(Z)-6-(3-hydroxyphenyl)hex-3-en-1,5-diynyl]phenol
—— 3-[(Z)-6-(3-hydroxyphenyl)hex-3-en-1,5-diynyl]phenol;oxygen(2-);vanadium —— C36H24O5V-2
3-[(Z)-6-(3-hydroxyphenyl)hex-3-en-1,5-diynyl]phenol;oxygen(2-);vanadium
—— 1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol;2-[[4-[(4R)-4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl]phenyl]hydrazinylidene]propanedinitrile —— C29H37N7O4
1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol;2-[[4-[(4R)-4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl]phenyl]hydrazinylidene]propanedinitrile
—— prop-2-enyl (4R)-6-[2-(5-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate —— C27H26ClN3O5S
prop-2-enyl (4R)-6-[2-(5-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
—— prop-2-enyl (4S)-6-[2-(5-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate —— C27H26ClN3O5S
prop-2-enyl (4S)-6-[2-(5-chloro-2-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
—— prop-2-enyl (4S)-6-[2-(3-chloro-4-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate —— C27H26ClN3O5S
prop-2-enyl (4S)-6-[2-(3-chloro-4-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
—— prop-2-enyl (4R)-6-[2-(3-chloro-4-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate —— C27H26ClN3O5S
prop-2-enyl (4R)-6-[2-(3-chloro-4-methylanilino)-2-oxoethyl]sulfanyl-5-cyano-4-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,4-dihydropyridine-3-carboxylate
—— 2,4,6-tris(2',4'-dihydroxy phenyl amino)-1,3,5-triazine —— C21H18N6O6
2,4,6-tris(2',4'-dihydroxy phenyl amino)-1,3,5-triazine
—— 3-[4-[[amino(thiophen-2-yl)methylidene]amino]phenyl]-N-(6-hydroxy-2,3,4-trimethoxyphenyl)propanamide —— C23H25N3O5S
3-[4-[[amino(thiophen-2-yl)methylidene]amino]phenyl]-N-(6-hydroxy-2,3,4-trimethoxyphenyl)propanamide
—— 4-[[(2,6-Dimethylpyridin-3-yl)amino]-di(propan-2-yloxy)phosphorylmethyl]-2-methoxy-6-methylphenol —— C22H33N2O5P
4-[[(2,6-Dimethylpyridin-3-yl)amino]-di(propan-2-yloxy)phosphorylmethyl]-2-methoxy-6-methylphenol
—— 4-[(2-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-(4-hydroxy-3-methylphenyl)but-1-enyl]-5-oxocyclopentyl}ethyl)sulfanyl]butanoic acid —— C22H30O6S
4-[(2-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-(4-hydroxy-3-methylphenyl)but-1-enyl]-5-oxocyclopentyl}ethyl)sulfanyl]butanoic acid
—— 5-chloro-3-[(2Z,4E)-5-(2,6-dimethyl-3-oxocyclohexyl)-3-methylpenta-2,4-dienyl]-2-hydroxy-4-methoxy-6-methylbenzaldehyde —— C23H29ClO4
5-chloro-3-[(2Z,4E)-5-(2,6-dimethyl-3-oxocyclohexyl)-3-methylpenta-2,4-dienyl]-2-hydroxy-4-methoxy-6-methylbenzaldehyde
—— 3-[1-(5-Nitropyrid-2-yl)-4-piperidinylamino]-1-(4-hydroxyphenoxy)-2-propanol 252578-00-0 C19H24N4O5
3-[1-(5-Nitropyrid-2-yl)-4-piperidinylamino]-1-(4-hydroxyphenoxy)-2-propanol
—— 3-[2-[(Dimethylamino)methyl]-6-(2-phenylethyl)cyclohepten-1-yl]phenol —— C24H31NO
3-[2-[(Dimethylamino)methyl]-6-(2-phenylethyl)cyclohepten-1-yl]phenol
—— 3-[2-[(Dimethylamino)methyl]-6-(2-phenylethyl)cyclohepten-1-yl]phenol;hydrochloride —— C24H32ClNO
3-[2-[(Dimethylamino)methyl]-6-(2-phenylethyl)cyclohepten-1-yl]phenol;hydrochloride
—— (2E,5S)-2-[(1-ethyl-3-methylpyrazol-4-yl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide —— C28H27N5O4S
(2E,5S)-2-[(1-ethyl-3-methylpyrazol-4-yl)methylidene]-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-3-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide
—— 3-[6-[(dimethylamino)methyl]-8,9-dihydro-7H-benzo[7]annulen-5-yl]phenol;hydrochloride —— C20H24ClNO
3-[6-[(dimethylamino)methyl]-8,9-dihydro-7H-benzo[7]annulen-5-yl]phenol;hydrochloride
—— 2-[3-(2H-benzimidazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate —— C19H18N2O3
2-[3-(2H-benzimidazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate
—— N,N'-bis[(4-hydroxyphenyl)methyl]propanediamide —— C17H18N2O4
N,N'-bis[(4-hydroxyphenyl)methyl]propanediamide
—— 1-(4-hydroxy-3-methoxyphenyl)dodecan-5-ol —— C19H32O3
1-(4-hydroxy-3-methoxyphenyl)dodecan-5-ol
—— N-(6-hydroxyhexyl)-3-(4-hydroxyphenyl)propanamide —— C15H23NO3
N-(6-hydroxyhexyl)-3-(4-hydroxyphenyl)propanamide
—— 6,7-dihydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide —— C18H29NO5
6,7-dihydroxy-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
—— 5-{[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino}-2-methoxyphenol 507488-12-2 C16H16N4O2S
5-{[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino}-2-methoxyphenol
—— (E,E)-2-(β-ethanolaminocarbonyl)-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile 368836-90-2 C16H18N2O5
(E,E)-2-(β-ethanolaminocarbonyl)-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile
—— N-[2-(3,4-dihydroxyphenyl)ethyl]-O-hexylurethane —— C17H27NO4
N-[2-(3,4-dihydroxyphenyl)ethyl]-O-hexylurethane