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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-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenol 247132-70-3 C15H21NO4
4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenol
—— 3-(2-Phenethylamino)-1-(4-(2-methoxyethyl)-2-bromophenoxy)-propanol-2 tartrate 74027-38-6 C24H32BrNO9
3-(2-Phenethylamino)-1-(4-(2-methoxyethyl)-2-bromophenoxy)-propanol-2 tartrate
—— Phenol, dihexyl- 73986-84-2 C18H30O
Phenol, dihexyl-
—— 1-(4-(2-Methoxyethyl)phenoxy)-3-((3-phenylpropyl)amino)-2-propanol hydrochloride 74027-45-5 C21H30ClNO3
1-(4-(2-Methoxyethyl)phenoxy)-3-((3-phenylpropyl)amino)-2-propanol hydrochloride
—— 1-(4-(2-Methoxyethyl)phenoxy)-3-((2-phenylethyl)amino)-2-propanol hydrochloride 74027-35-3 C20H28ClNO3
1-(4-(2-Methoxyethyl)phenoxy)-3-((2-phenylethyl)amino)-2-propanol hydrochloride
—— 3-(3-Hydroxy-2-methoxy-phenyl)-propionaldehyde 138644-19-6 C10H12O3
3-(3-Hydroxy-2-methoxy-phenyl)-propionaldehyde
—— 1-(4-(2-Methoxyethyl)phenoxy)-3-((phenylmethyl)amino)-2-propanol hydrochloride 74027-44-4 C19H26ClNO3
1-(4-(2-Methoxyethyl)phenoxy)-3-((phenylmethyl)amino)-2-propanol hydrochloride
—— 4-(2-((2-Hydroxy-3-(4-(2-methoxyethyl)phenoxy)propyl)amino)ethyl)phenol hydrochloride 74027-36-4 C20H28ClNO4
4-(2-((2-Hydroxy-3-(4-(2-methoxyethyl)phenoxy)propyl)amino)ethyl)phenol hydrochloride
—— 2-(2-pyrimidyl)phenol 64435-20-7 C10H8N2O
2-(2-pyrimidyl)phenol
—— 4-(3-ethyl-3,7-dimethyloctyl)-2-iodophenol 1361320-45-7 C18H29IO
4-(3-ethyl-3,7-dimethyloctyl)-2-iodophenol
—— 2,6-dibromo-4-(3-ethyl-3,7-dimethyloctyl)phenol 1361320-56-0 C18H28Br2O
2,6-dibromo-4-(3-ethyl-3,7-dimethyloctyl)phenol
—— 2,3,7,8,16,17-hexahydrobakuchiol 10309-38-3 C18H30O
2,3,7,8,16,17-hexahydrobakuchiol
—— (1S)-N-(trifluoroacetyl)-1-(5-hydroxy-3-methoxyphenyl)-2-(methoxyethoxy-methoxy)ethylamine 296252-48-7 C15H20F3NO6
(1S)-N-(trifluoroacetyl)-1-(5-hydroxy-3-methoxyphenyl)-2-(methoxyethoxy-methoxy)ethylamine
—— 3,5,6-Trichlor-1-hydroxy-2-methoxy-4-methyl-benzol 33963-40-5 C8H7Cl3O2
3,5,6-Trichlor-1-hydroxy-2-methoxy-4-methyl-benzol
—— 5-Hydroxy-3-methyl-diphenylamin 14152-08-0 C13H13NO
5-Hydroxy-3-methyl-diphenylamin
—— (Z)-5-(2,3,4-trihydroxybenzylidene)-2-thioxothiazolidin-4-one 1208534-98-8 C10H7NO4S2
(Z)-5-(2,3,4-trihydroxybenzylidene)-2-thioxothiazolidin-4-one
—— 2,3-dimethoxy-4-methylphenol 6375-85-5 C9H12O3
2,3-dimethoxy-4-methylphenol
—— 3-Methoxy-4-methyl-benzene-1,2-diol 129627-05-0 C8H10O3
3-Methoxy-4-methyl-benzene-1,2-diol
—— 2,3,4-trihydroxy-5-(pyrrolidin-1-ylmethyl)benzaldehyde 1033037-76-1 C12H15NO4
2,3,4-trihydroxy-5-(pyrrolidin-1-ylmethyl)benzaldehyde
—— (E)-2-((benzylimino)methyl)-4-chlorophenol —— C14H12ClNO
(E)-2-((benzylimino)methyl)-4-chlorophenol
—— 2-(3-chloro-4-fluorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-4-thiazolidinone 881940-82-5 C17H12ClFN2O3S
2-(3-chloro-4-fluorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-4-thiazolidinone
—— 5-(3,4-dihydro-2H-pyran-2-yl)-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one 1024608-13-6 C21H23N3O4
5-(3,4-dihydro-2H-pyran-2-yl)-3-hydroxy-4-(4-hydroxy-phenyl)-1-(3-imidazol-1-yl-propyl)-1,5-dihydro-pyrrol-2-one
—— 2-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol 1025366-12-4 C22H24ClN7O
2-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol
—— (5S,13S)-19-[2-(2,5-diethynylphenyl)ethynyl]-5,13-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol 1381766-29-5 C40H36O6
(5S,13S)-19-[2-(2,5-diethynylphenyl)ethynyl]-5,13-diphenyl-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol
—— (5S,13S)-5,13-diphenyl-19-[2-[2-(2-trimethylsilylethynyl)-5-[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol 864920-10-5 C52H64O6Si2
(5S,13S)-5,13-diphenyl-19-[2-[2-(2-trimethylsilylethynyl)-5-[2-tri(propan-2-yl)silylethynyl]phenyl]ethynyl]-3,6,9,12,15-pentaoxabicyclo[15.3.1]henicosa-1(20),17(21),18-trien-21-ol
—— dimethyl 2,5-dihydroxy-1,4-benzenediacetate 13949-86-5 C12H14O6
dimethyl 2,5-dihydroxy-1,4-benzenediacetate
—— 4-bromo-2-{(E)-[(2-fluorophenyl)imino]methyl}phenol 325471-45-2 C13H9BrFNO
4-bromo-2-{(E)-[(2-fluorophenyl)imino]methyl}phenol
—— 2-Bromo-6-methoxy-4-(phenyliminomethyl)phenol 238422-32-7 C14H12BrNO2
2-Bromo-6-methoxy-4-(phenyliminomethyl)phenol
—— 2,3-Dimethoxy-6-vinyl-phenol 855410-03-6 C10H12O3
2,3-Dimethoxy-6-vinyl-phenol
—— 6-chloro-2-(3-hydroxypropyl)-3-methylphenol 1154740-70-1 C10H13ClO2
6-chloro-2-(3-hydroxypropyl)-3-methylphenol
—— 5-[2-(2-chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one 1246383-01-6 C16H15ClF3NO3
5-[2-(2-chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one
—— Hydron;4-(1-hydroxy-2-imidazol-1-ylethyl)phenol;chloride —— C11H13ClN2O2
Hydron;4-(1-hydroxy-2-imidazol-1-ylethyl)phenol;chloride
—— 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyrrole-2-carbonitrile 1246383-24-3 C16H14ClF3N2O2
5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyrrole-2-carbonitrile
—— 2,4,5-Trifluororesorcinol 35770-72-0 C6H3F3O2
2,4,5-Trifluororesorcinol
—— 5-[2-(2-chloro-5-fluoro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one 1246383-05-0 C16H14ClF4NO3
5-[2-(2-chloro-5-fluoro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one
—— 5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-pyridine-2-carbonitrile 1246383-22-1 C17H14ClF3N2O2
5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-pyridine-2-carbonitrile
—— 3-chloro-5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one 1246383-14-1 C16H14Cl2F3NO3
3-chloro-5-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one
—— 5-(3,4-dihydroxybenzyl)thiazolidine-2,4-dione 79525-05-6 C10H9NO4S
5-(3,4-dihydroxybenzyl)thiazolidine-2,4-dione
—— 2-(2',3'-Dihydroxy-1'-methyl-propyl)phenol 71816-68-7 C10H14O3
2-(2',3'-Dihydroxy-1'-methyl-propyl)phenol
—— 2-[2-(1-Hydroxy-cyclopentyl)-1-methyl-ethyl]-phenol 74181-02-5 C14H20O2
2-[2-(1-Hydroxy-cyclopentyl)-1-methyl-ethyl]-phenol
—— 3-(2-hydroxyphenyl)cyclobutanone 294669-29-7 C10H10O2
3-(2-hydroxyphenyl)cyclobutanone
—— N-[2-(3-hydroxyphenyl)ethyl]-N-methylacetamide 1057214-74-0 C11H15NO2
N-[2-(3-hydroxyphenyl)ethyl]-N-methylacetamide
—— 6,6′-{(2-(dimethylamino)ethyl azanediyl)bis(methylene)}bis(2-methoxy-4-methylphenol) 1620325-37-2 C22H32N2O4
6,6′-{(2-(dimethylamino)ethyl azanediyl)bis(methylene)}bis(2-methoxy-4-methylphenol)
—— 2-hydroxy-6-methoxy-3-<2-(N,N-dipropylamino)ethyl>aniline 101626-39-5 C15H26N2O2
2-hydroxy-6-methoxy-3-<2-(N,N-dipropylamino)ethyl>aniline
—— [(3S)-oxolan-3-yl] N-[(3-hydroxyphenyl)methyl]carbamate 248251-00-5 C12H15NO4
[(3S)-oxolan-3-yl] N-[(3-hydroxyphenyl)methyl]carbamate
—— (4S,9S,19S,24S,34S,39S)-14,29,44-trimethyl-3,10,18,25,33,40-hexazaheptacyclo[40.3.1.112,16.127,31.04,9.019,24.034,39]octatetraconta-1(45),12,14,16(48),27(47),28,30,42(46),43-nonaene-46,47,48-triol 1147271-04-2 C45H66N6O3
(4S,9S,19S,24S,34S,39S)-14,29,44-trimethyl-3,10,18,25,33,40-hexazaheptacyclo[40.3.1.112,16.127,31.04,9.019,24.034,39]octatetraconta-1(45),12,14,16(48),27(47),28,30,42(46),43-nonaene-46,47,48-triol
—— 5-(4-hydroxyphenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride 158720-79-7 C16H21NO*ClH
5-(4-hydroxyphenyl)-1-azaspiro[5.5]undec-4-ene hydrochloride
—— 4-(4-Chloro-2-hydroxy-phenyl)-5,6-dimethyl-4,5-dihydro-2H-[1,2,4]triazin-3-one 113922-43-3 C11H12ClN3O2
4-(4-Chloro-2-hydroxy-phenyl)-5,6-dimethyl-4,5-dihydro-2H-[1,2,4]triazin-3-one
—— Pyridine, 4-(2-(N-(2-(dimethylamino)ethyl)-m-toluidino)ethyl)-, dipicrate 97829-45-3 C30H31N9O14
Pyridine, 4-(2-(N-(2-(dimethylamino)ethyl)-m-toluidino)ethyl)-, dipicrate
—— Pyridine, 4-(2-(N-(2-(dimethylamino)ethyl)anilino)ethyl)-, dipicrate 98271-00-2 C29H29N9O14
Pyridine, 4-(2-(N-(2-(dimethylamino)ethyl)anilino)ethyl)-, dipicrate