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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
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one 99985-06-5 C11H10N2O3S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 1,3-Benzenediol, 4-(1,2,3,6-tetrahydro-2,2,6,6-tetramethyl-4-pyridinyl)- 90747-13-0 C15H21NO2
1,3-Benzenediol, 4-(1,2,3,6-tetrahydro-2,2,6,6-tetramethyl-4-pyridinyl)-
—— diphenyl (2,5-dihydroxyphenyl)phosphonate 1384457-19-5 C18H15O5P
diphenyl (2,5-dihydroxyphenyl)phosphonate
—— 5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one 359899-47-1 C13H12BrNO3S2
5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— Ethyl (8Z)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-2-(4-methylphenyl)-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate 5667-90-3 C25H24N2O5S
Ethyl (8Z)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-2-(4-methylphenyl)-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate
—— Ethyl (8Z)-2-(3,4-dimethoxyphenyl)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate 5679-64-1 C26H26N2O7S
Ethyl (8Z)-2-(3,4-dimethoxyphenyl)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate
—— 3-bromo-2-hydroxy-6-methoxybenzaldehyde 29866-53-3 C8H7BrO3
3-bromo-2-hydroxy-6-methoxybenzaldehyde
—— 4-hydroxyphenyl-N,N-dimethylimide 33709-30-7 C9H11NO
4-hydroxyphenyl-N,N-dimethylimide
—— 1,2-Dimethoxy-4-[2-(methoxymethoxy)ethyl]benzene 1338236-55-7 C12H18O4
1,2-Dimethoxy-4-[2-(methoxymethoxy)ethyl]benzene
—— 4-chloro-2-[(3-dimethylaminopropylimino)methyl]phenol 1489230-36-5 C12H17ClN2O
4-chloro-2-[(3-dimethylaminopropylimino)methyl]phenol
—— 2-tert-butyl-4-fluoro-5-nitrophenol 873055-44-8 C10H12FNO3
2-tert-butyl-4-fluoro-5-nitrophenol
—— (E)-3-(3-hydroxy-4-methoxybenzylidene)-1-methylindolin-2-one 1148119-20-3 C17H15NO3
(E)-3-(3-hydroxy-4-methoxybenzylidene)-1-methylindolin-2-one
—— ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 5832-47-3 C25H23BrN2O6S
ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol 868849-46-1 C14H21NO2
4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol
—— methyl [2-(3,5-dibromo-4-hydroxyphenyl)ethyl]carbamate 62372-09-2 C10H11Br2NO3
methyl [2-(3,5-dibromo-4-hydroxyphenyl)ethyl]carbamate
—— tert-butyl (2-hydroxy-1-(3-hydroxyphenyl)ethyl)carbamate 1454273-67-6 C13H19NO4
tert-butyl (2-hydroxy-1-(3-hydroxyphenyl)ethyl)carbamate
—— Tert-butyl [3-hydroxy-2-methyl-4-(3-methylbutyl)phenyl] carbonate 679433-33-1 C17H26O4
Tert-butyl [3-hydroxy-2-methyl-4-(3-methylbutyl)phenyl] carbonate
—— 2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate 1159795-87-5 C18H29BrO5Si
2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate
—— (2-{N'-[1-(3-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-oxo-4,5-dihydro-thiazol-5-yl)-acetic acid 21938-65-8 C12H11N3O4S
(2-{N'-[1-(3-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-oxo-4,5-dihydro-thiazol-5-yl)-acetic acid
—— 1-(3-hydroxy-phenyl)-nonadecan-2-one 501-09-7 C25H42O2
1-(3-hydroxy-phenyl)-nonadecan-2-one
—— 5-methyl-thiophene-2-carbaldehyde-(4-hydroxy-phenylimine) 91569-00-5 C12H11NOS
5-methyl-thiophene-2-carbaldehyde-(4-hydroxy-phenylimine)
—— 4-tert-butyl-2-chloro-5-nitrophenol 873055-60-8 C10H12ClNO3
4-tert-butyl-2-chloro-5-nitrophenol
—— 4-dimethylaminomethyl-2,6-dimethylphenol 83037-96-1 C10H15NO
4-dimethylaminomethyl-2,6-dimethylphenol
—— 2-{(E)-[(5-Methylthiophen-2-yl)methylidene]amino}-4-nitrophenol 60957-41-7 C12H10N2O3S
2-{(E)-[(5-Methylthiophen-2-yl)methylidene]amino}-4-nitrophenol
—— 2-Hydroxy-5-methoxy-3-methylbenzylalkohol 5600-81-7 C9H12O3
2-Hydroxy-5-methoxy-3-methylbenzylalkohol
—— 2-[(1H-benzimidazol-2-ylhydrazinylidene)methyl]-4-methoxyphenol 130880-01-2 C15H14N4O2
2-[(1H-benzimidazol-2-ylhydrazinylidene)methyl]-4-methoxyphenol
—— 2-[[4-[(3-Chlorophenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol 6108-09-4 C19H23ClN2O2
2-[[4-[(3-Chlorophenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol
—— ethyl 4-(5-chloro-2-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 6375-59-3 C15H17ClN2O5
ethyl 4-(5-chloro-2-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 3-Chloro-6-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]pyridazine 160951-24-6 C15H15ClN2O3
3-Chloro-6-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]pyridazine
—— Ethyl 2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 6173-07-5 C21H17BrN2O4S2
Ethyl 2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 2-(2-hydroxy-5-methylphenyl)-4,4,8-trimethyl-5H-[1,2]thiazolo[5,4-c]quinoline-1-thione 6174-46-5 C20H20N2OS2
2-(2-hydroxy-5-methylphenyl)-4,4,8-trimethyl-5H-[1,2]thiazolo[5,4-c]quinoline-1-thione
—— 2,4-diamino-5-(3-allyl-4-hydroxy-5-methoxybenzyl)pyrimidine 121936-21-8 C15H18N4O2
2,4-diamino-5-(3-allyl-4-hydroxy-5-methoxybenzyl)pyrimidine
—— 6-(2-hydroxy-3-{2-[2-(4-hydroxy-3,5-dimethoxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-propyl)-2,2-dimethyl-[1,3]-dioxin-4-one 1139819-27-4 C23H32O7S2
6-(2-hydroxy-3-{2-[2-(4-hydroxy-3,5-dimethoxyphenyl)-ethyl]-[1,3]-dithian-2-yl}-propyl)-2,2-dimethyl-[1,3]-dioxin-4-one
—— 2-{2-[2-(4-hydroxy-3,5-dimethoxyphenyl)-ethyl]-[1,3]dithian-2-yl}acetaldehyde 1139819-23-0 C16H22O4S2
2-{2-[2-(4-hydroxy-3,5-dimethoxyphenyl)-ethyl]-[1,3]dithian-2-yl}acetaldehyde
—— Methyl 6-(4-hydroxy-3-nitrophenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate 6380-94-5 C14H15N3O6
Methyl 6-(4-hydroxy-3-nitrophenyl)-3,4-dimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
—— 3,3-bis-(4-hydroxy-3-methoxy-phenyl)-indolin-2-one 47561-94-4 C22H19NO5
3,3-bis-(4-hydroxy-3-methoxy-phenyl)-indolin-2-one
—— 4-Amino-5-hydroxy-benzocyclobuten 4082-27-3 C8H9NO
4-Amino-5-hydroxy-benzocyclobuten
—— 2,6-Dimethoxy-nitrosophenol 19628-74-1 C8H9NO4
2,6-Dimethoxy-nitrosophenol
—— 2,6-dimethoxy-4-hydroxyaniline 20032-71-7 C8H11NO3
2,6-dimethoxy-4-hydroxyaniline
—— 3,5-dimethoxy-4-nitrosophenol 136491-41-3 C8H9NO4
3,5-dimethoxy-4-nitrosophenol
—— 1-<2-<<2-hydroxy-3-(4-hydroxyphenoxy)propyl>amino>ethyl>urea 76167-26-5 C12H19N3O4
1-<2-<<2-hydroxy-3-(4-hydroxyphenoxy)propyl>amino>ethyl>urea
—— ICI 119033 76167-39-0 C19H25N3O4
ICI 119033
—— 1,1-Diethyl-3-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]urea 76167-29-8 C16H27N3O4
1,1-Diethyl-3-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]urea
—— 1,1-dimethyl-3-<2-<<2-hydroxy-3-(4-hydroxyphenoxy)propyl>amino>ethyl>urea 53672-84-7 C14H23N3O4
1,1-dimethyl-3-<2-<<2-hydroxy-3-(4-hydroxyphenoxy)propyl>amino>ethyl>urea
—— 1-[2-[[2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-3-(2-methoxyethyl)urea 76167-20-9 C15H25N3O5
1-[2-[[2-Hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-3-(2-methoxyethyl)urea
—— 1-(2-Hydroxyethyl)-3-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]urea 71676-19-2 C14H23N3O5
1-(2-Hydroxyethyl)-3-[2-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]urea
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione 58215-62-6 C11H8BrNO4S
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 4-[(Cyclohexylamino)methyl]-2-methoxyphenol;hydrochloride 5427-38-3 C14H22ClNO2
4-[(Cyclohexylamino)methyl]-2-methoxyphenol;hydrochloride
—— 2-[(Cyclohexylamino)methyl]-6-methoxyphenol hydrochloride 5442-65-9 C14H22ClNO2
2-[(Cyclohexylamino)methyl]-6-methoxyphenol hydrochloride
—— 2-chloro-5-[[(5-(o-hydroxy-p-methoxyphenyl)-1,3,4-oxadiazol-2-yl)thio]methyl]pyridine 1257842-99-1 C15H12ClN3O3S
2-chloro-5-[[(5-(o-hydroxy-p-methoxyphenyl)-1,3,4-oxadiazol-2-yl)thio]methyl]pyridine