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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
—— 3,6-dichloro-benzene-1,2,4-triol 149312-96-9 C6H4Cl2O3
3,6-dichloro-benzene-1,2,4-triol
—— 2,4-Dihydroxyphenylethylidenebenzylamine 82488-62-8 C15H15NO2
2,4-Dihydroxyphenylethylidenebenzylamine
—— (2R)-N-Cyclopropyl-2-(4-hydroxyphenoxy)propanamide 496865-97-5 C12H15NO3
(2R)-N-Cyclopropyl-2-(4-hydroxyphenoxy)propanamide
—— 1-(2,4-dihydroxyphenyl)-3-(furan-2-yl)propenone 1356850-08-2 C13H10O4
1-(2,4-dihydroxyphenyl)-3-(furan-2-yl)propenone
—— 3,4,5-tribromophenol 116434-90-3 C6H3Br3O
3,4,5-tribromophenol
—— 4-[(1S)-1-Hydroxyethyl]benzene-1,3-diol 669088-57-7 C8H10O3
4-[(1S)-1-Hydroxyethyl]benzene-1,3-diol
—— (E)-3-(furan-2-yl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one 1345959-97-8 C13H10O4
(E)-3-(furan-2-yl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one
—— 2-iodo-4-(trifluoromethoxy) phenol 405517-54-6 C7H4F3IO2
2-iodo-4-(trifluoromethoxy) phenol
—— 1-[3-(2,4-Dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone 686717-90-8 C18H18N2O4
1-[3-(2,4-Dihydroxy-phenyl)-5-(2-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone
—— 1,3-Benzenediol, 4-(1-((3-(1H-imidazol-1-yl)propyl)imino)ethyl)- 1313999-39-1 C14H17N3O2
1,3-Benzenediol, 4-(1-((3-(1H-imidazol-1-yl)propyl)imino)ethyl)-
—— 2,5-dimethyl-1,3,4-trihydroxybenzene 4380-95-4 C8H10O3
2,5-dimethyl-1,3,4-trihydroxybenzene
—— 2,2,2-trichloro-1-(4-hydroxy-3-methoxy-phenyl)-ethanol 50597-26-7 C9H9Cl3O3
2,2,2-trichloro-1-(4-hydroxy-3-methoxy-phenyl)-ethanol
—— 2,4,5,6-tetramethyl-resorcinol 139054-54-9 C10H14O2
2,4,5,6-tetramethyl-resorcinol
—— 5-hydroxy-3-methylorcinaldehyde 858489-50-6 C9H10O4
5-hydroxy-3-methylorcinaldehyde
—— 4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol 1346653-06-2 C20H16ClN3O
4-chloro-2-(5-phenyl-1-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol
—— 2-(2-amino-6<i>H</i>-[1,3,4]thiadiazin-5-yl)-benzene-1,4-diol 60912-86-9 C9H9N3O2S
2-(2-amino-6<i>H</i>-[1,3,4]thiadiazin-5-yl)-benzene-1,4-diol
—— Carbamic acid, [(5-hydroxy-1,3-phenylene)bis(methylene)]bis[[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]-, bis(1,1-dimethylethyl) ester 289910-01-6 C32H54N4O9
Carbamic acid, [(5-hydroxy-1,3-phenylene)bis(methylene)]bis[[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]-, bis(1,1-dimethylethyl) ester
—— 4-(2-amino-thiazol-4-yl)-benzene-1,2,3-triol 20217-18-9 C9H8N2O3S
4-(2-amino-thiazol-4-yl)-benzene-1,2,3-triol
—— 4-(2-hydrazino-thiazol-4-yl)-benzene-1,2,3-triol 23251-23-2 C9H9N3O3S
4-(2-hydrazino-thiazol-4-yl)-benzene-1,2,3-triol
—— 4-hydroxy-2,6-dimethyl-benzaldehyde-oxime 855265-31-5 C9H11NO2
4-hydroxy-2,6-dimethyl-benzaldehyde-oxime
—— 2-methylthio-3,5-dimethylphenol 25674-57-1 C9H12OS
2-methylthio-3,5-dimethylphenol
—— 2,6-dibromo-3,5-dimethylphenol 83385-86-8 C8H8Br2O
2,6-dibromo-3,5-dimethylphenol
—— 1-(3,5-dimethylpiperidin-1-yl)-3-(4,6-dimethoxy-2-hydroxyphenyl)-3-(2-methylimidazol-4-yl)propan-1-one —— C22H31N3O4
1-(3,5-dimethylpiperidin-1-yl)-3-(4,6-dimethoxy-2-hydroxyphenyl)-3-(2-methylimidazol-4-yl)propan-1-one
—— 3-(2-hydroxyphenyl)-N-[4-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]butyl]propanamide 1450833-24-5 C19H30N2O6
3-(2-hydroxyphenyl)-N-[4-[(2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]butyl]propanamide
—— 2-[(E)-[(3-morpholin-4-ylpropyl)imino]methyl]phenol 1396756-29-8 C14H20N2O2
2-[(E)-[(3-morpholin-4-ylpropyl)imino]methyl]phenol
—— 3,6-dimethoxy-4,5-dichlorocatechol 109765-61-9 C8H8Cl2O4
3,6-dimethoxy-4,5-dichlorocatechol
—— 3-hydroxy-N-(4-hydroxy-3-methoxybenzyl)octanamide 1331858-67-3 C16H25NO4
3-hydroxy-N-(4-hydroxy-3-methoxybenzyl)octanamide
—— 4-bromo-3,6-dimethoxycatechol 109765-62-0 C8H9BrO4
4-bromo-3,6-dimethoxycatechol
—— 4-bromo-3,6-dimethoxysalicylaldehyde 65162-35-8 C9H9BrO4
4-bromo-3,6-dimethoxysalicylaldehyde
—— 2-methoxy-4-tert-butylcatechol 74752-72-0 C11H16O3
2-methoxy-4-tert-butylcatechol
—— 1-[(4-Tert-butylphenyl)methyl]-3-[1-(4-hydroxy-3-methoxyphenyl)ethyl]thiourea 1391847-98-5 C21H28N2O2S
1-[(4-Tert-butylphenyl)methyl]-3-[1-(4-hydroxy-3-methoxyphenyl)ethyl]thiourea
—— N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-4-methyl-1,2-dithiolane-4-carboxamide 1216851-85-2 C14H19NO3S2
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-4-methyl-1,2-dithiolane-4-carboxamide
—— 2-hydroxy-4-nitroaniline diazonium salt 24726-35-0 C6H4N3O3
2-hydroxy-4-nitroaniline diazonium salt
—— 3-(2-hydroxy-3,5-dinitrophenylhydrazo)pentane-2,4-dione 658080-19-4 C11H10N4O7
3-(2-hydroxy-3,5-dinitrophenylhydrazo)pentane-2,4-dione
—— 3-(N,N-dimethylcarbamoyloxy)-2,6-diiodo-5-methoxyphenol 139220-60-3 C10H11I2NO4
3-(N,N-dimethylcarbamoyloxy)-2,6-diiodo-5-methoxyphenol
—— 2,4,6-tri(phenylmethyloxy)phenol 22132-85-0 C27H24O4
2,4,6-tri(phenylmethyloxy)phenol
—— Methyl 11-(3,5-dihydroxyphenoxy)undecanoate 1150586-39-2 C18H28O5
Methyl 11-(3,5-dihydroxyphenoxy)undecanoate
—— 4-(3-hydroxyphenyl)-3-(dimethylaminomethyl)thiacyclohexan-4-ol 119558-20-2 C14H21NO2S
4-(3-hydroxyphenyl)-3-(dimethylaminomethyl)thiacyclohexan-4-ol
—— 3-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonic acid 1221900-45-3 C11H11N3O8S
3-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonic acid
—— (+/-)-1-(3,4-dimethoxy-2-hydroxyphenethyl)-5-ethyl-2-piperidone 89680-97-7 C17H25NO4
(+/-)-1-(3,4-dimethoxy-2-hydroxyphenethyl)-5-ethyl-2-piperidone
—— (+/-)-1-(3,4-dimethoxy-2-hydroxyphenethyl)-3-ethyl-2-piperidone 109741-73-3 C17H25NO4
(+/-)-1-(3,4-dimethoxy-2-hydroxyphenethyl)-3-ethyl-2-piperidone
—— methyl (6-hydroxy-2-methoxyphenyl)acetate 628330-49-4 C10H12O4
methyl (6-hydroxy-2-methoxyphenyl)acetate
—— 3,6-Dimethoxy-2-(3-methylbut-2-enyl)phenol 411232-95-6 C13H18O3
3,6-Dimethoxy-2-(3-methylbut-2-enyl)phenol
—— 4-chloro-2-methyl-3-nitrophenol 219312-11-5 C7H6ClNO3
4-chloro-2-methyl-3-nitrophenol
—— tert-butyl (R)-4-(4-hydroxyphenyl)-2,2-dimethyloxazolidine-3-carboxylate 143674-61-7 C16H23NO4
tert-butyl (R)-4-(4-hydroxyphenyl)-2,2-dimethyloxazolidine-3-carboxylate
—— 8-(p-hydroxyphenyl)octyl bromide 95962-76-8 C14H21BrO
8-(p-hydroxyphenyl)octyl bromide
—— 5-(benzyloxy)-4-bromo-2-hydroxybenzaldehyde 775335-97-2 C14H11BrO3
5-(benzyloxy)-4-bromo-2-hydroxybenzaldehyde
—— 2-<N-<1-(3,4-dihydroxyphenyl)ethyl>amino>acetaldehyde dimethyl acetal hydrochloride 92366-89-7 C12H19NO4*ClH
2-<N-<1-(3,4-dihydroxyphenyl)ethyl>amino>acetaldehyde dimethyl acetal hydrochloride
—— Diethyl [(3-chloro-4-hydroxyphenyl)methyl]propanedioate 124389-55-5 C14H17ClO5
Diethyl [(3-chloro-4-hydroxyphenyl)methyl]propanedioate
—— pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide 305339-15-5 C14H13N3O3
pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide