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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
—— 3,4,6-Tris-<dimethylaminomethyl>-brenzcatechin 964-24-9 C15H27N3O2
3,4,6-Tris-<dimethylaminomethyl>-brenzcatechin
—— (μ-oxalato)di[perchlorato(1-benzyl-4,7-dimethyl-1,4,7-triaza-cyclononane)copper(II)] 951033-04-8 C32H50Cl2Cu2N6O12
(μ-oxalato)di[perchlorato(1-benzyl-4,7-dimethyl-1,4,7-triaza-cyclononane)copper(II)]
—— 1569090-80-7 C12H11N3O
—— 4-Hydroxy-3,5-dinitrobenzylchlorid 77691-32-8 C7H5ClN2O5
4-Hydroxy-3,5-dinitrobenzylchlorid
—— 2-((1-(1-adamantan-1-yl)ethyl)-imino-methyl)-6-methoxyphenol 1313594-90-9 C20H27NO2
2-((1-(1-adamantan-1-yl)ethyl)-imino-methyl)-6-methoxyphenol
—— 4-(4-chlorophenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-thiosemicarbazide 16434-24-5 C15H14ClN3O2S
4-(4-chlorophenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-thiosemicarbazide
—— 4,4',4''-(nitrilotris(methylene))tris(2-methoxyphenol) 1372608-33-7 C24H27NO6
4,4',4''-(nitrilotris(methylene))tris(2-methoxyphenol)
—— 2-methoxy-4-(pyrrolidin-1-ylmethyl)phenol 498577-19-8 C12H17NO2
2-methoxy-4-(pyrrolidin-1-ylmethyl)phenol
—— 4-(hydrazonomethyl)-2-methoxyphenol 1527-84-0 C8H10N2O2
4-(hydrazonomethyl)-2-methoxyphenol
—— (4-(5-(hydroxymethyl)-5-methyl-1,3-dioxan-2-yl)-2-methoxyphenol) 1089332-89-7 C13H18O5
(4-(5-(hydroxymethyl)-5-methyl-1,3-dioxan-2-yl)-2-methoxyphenol)
—— 2-cinnamyl-3,5-dimethylphenol 93651-50-4 C17H18O
2-cinnamyl-3,5-dimethylphenol
—— 2-methoxy-4-((pyridine-2-ylimino)methyl)phenol 74734-31-9 C13H12N2O2
2-methoxy-4-((pyridine-2-ylimino)methyl)phenol
—— 2-methoxy-4-[(2-methyl-1H-indol-3-yl)(2-methyl-3H-indol-3-ylidene)methyl]phenol 1616722-77-0 C26H22N2O2
2-methoxy-4-[(2-methyl-1H-indol-3-yl)(2-methyl-3H-indol-3-ylidene)methyl]phenol
—— 2-(((1-(adamantan-1-yl)ethyl)imino)methyl)-4-bromophenol 201992-21-4 C19H24BrNO
2-(((1-(adamantan-1-yl)ethyl)imino)methyl)-4-bromophenol
—— 2-((4R,5S)-4-methyl-5-phenyl-4,5-dihydrooxazole-2-yl)phenol 1421593-25-0 C16H15NO2
2-((4R,5S)-4-methyl-5-phenyl-4,5-dihydrooxazole-2-yl)phenol
—— Et4N [nickel(II) bis(2-mercapto-3-trimethylsilylphenyl)sulfide N3] 472958-20-6 C8H20N*C18H24N3NiS3Si2
Et4N [nickel(II) bis(2-mercapto-3-trimethylsilylphenyl)sulfide N3]
—— 4-[(4-bromo-phenylimino)-methyl]-2-methoxy-phenol 3382-70-5 C14H12BrNO2
4-[(4-bromo-phenylimino)-methyl]-2-methoxy-phenol
—— [Ag(saccharate)(2-(dimethylaminomethyl)-3-hydroxypyridine)] 911321-27-2 C15H16AgN3O4S
[Ag(saccharate)(2-(dimethylaminomethyl)-3-hydroxypyridine)]
—— 4-((2-(1H-tetrazol-5-yl)hydrazono)methyl)-2-methoxyphenol 56929-45-4 C9H10N6O2
4-((2-(1H-tetrazol-5-yl)hydrazono)methyl)-2-methoxyphenol
—— (5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oxime 193741-71-8 C11H12N2O4
(5,6-dihydro-[1,4,2]dioxazin-3-yl)-(2-hydroxy-phenyl)-methanone O-methyl-oxime
—— N-[[2-(1,3-dithian-2-yl)phenyl]methylidene]hydroxylamine 1313208-32-0 C11H13NOS2
N-[[2-(1,3-dithian-2-yl)phenyl]methylidene]hydroxylamine
—— 2-((1-(1-adamantan-1-yl)ethyl)iminomethyl)-4-chlorophenol 1638417-14-7 C19H24ClNO
2-((1-(1-adamantan-1-yl)ethyl)iminomethyl)-4-chlorophenol
—— adamantyl-N-(ethyl)-(5-chlorosalicylidene)aniline 391219-37-7 C19H24ClNO
adamantyl-N-(ethyl)-(5-chlorosalicylidene)aniline
—— 3-[2-(4-hydroxy-3-methoxybenzylidene)hydrazono]-5-chloroindolin-2-one 1393098-90-2 C16H12ClN3O3
3-[2-(4-hydroxy-3-methoxybenzylidene)hydrazono]-5-chloroindolin-2-one
—— (4-hydroxy-3-methoxyphenyl)(phenylamino)acetonitrile 223136-13-8 C15H14N2O2
(4-hydroxy-3-methoxyphenyl)(phenylamino)acetonitrile
—— (-)-capsaicinol 137493-35-7 C18H27NO4
(-)-capsaicinol
—— p-Nitrophenol-triethylamine 15852-96-7 C6H5NO3*C6H15N
p-Nitrophenol-triethylamine
—— 3-(2-hydroxyphenyl)-5-phenylisoxazoline 18732-46-2 C15H13NO2
3-(2-hydroxyphenyl)-5-phenylisoxazoline
—— 4-Dimethylaminomethyl-pyrogallol 942-55-2 C9H13NO3
4-Dimethylaminomethyl-pyrogallol
—— 1-(5-bromo-2-hydroxybenzylidene)-thiosemicarbazide 94794-28-2 C8H8BrN3OS
1-(5-bromo-2-hydroxybenzylidene)-thiosemicarbazide
—— 5-bromo-4-(4,6-diphenyl-1,3,5-triazin-2-yl)pyridin-3-ol 1616763-28-0 C20H13BrN4O
5-bromo-4-(4,6-diphenyl-1,3,5-triazin-2-yl)pyridin-3-ol
—— (2-hydroxy-3,5-diiodo-phenyl)-acetic acid 3583-18-4 C8H6I2O3
(2-hydroxy-3,5-diiodo-phenyl)-acetic acid
—— 2,4-dinitro-phenol; compound with triethylamine 20399-10-4 C6H4N2O5*C6H15N
2,4-dinitro-phenol; compound with triethylamine
—— tert-butyl 4-[3-bromo-4-[tert-butyl(dimethyl)silyl]oxy-5-methoxyphenyl]-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 850795-32-3 C23H35BrN2O5Si
tert-butyl 4-[3-bromo-4-[tert-butyl(dimethyl)silyl]oxy-5-methoxyphenyl]-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— N'-(2-hydroxy-4-methoxybenzylidene)-3-methylbenzohydrazide 463329-99-9 C16H16N2O3
N'-(2-hydroxy-4-methoxybenzylidene)-3-methylbenzohydrazide
—— p-Chlorphenol-triethylamin-Komplex 22300-97-6 C6H5ClO*C6H15N
p-Chlorphenol-triethylamin-Komplex
—— 1-((thioureidoimino)methyl)-3,5-dihydroxybenzene 857017-59-5 C8H9N3O2S
1-((thioureidoimino)methyl)-3,5-dihydroxybenzene
—— S-benzyl β-N-(2-hydroxyphenyl)methylenedithiocarbazate 26158-45-2 C15H14N2OS2
S-benzyl β-N-(2-hydroxyphenyl)methylenedithiocarbazate
—— 4-[(2-amino-4-{[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]amino}-6-methyl-pyrimidin-5-yl)methyl]-3-methoxyphenol 1376514-63-4 C25H42N4O3Si
4-[(2-amino-4-{[(3S)-1-{[tert-butyl(dimethyl)silyl]oxy}hexan-3-yl]amino}-6-methyl-pyrimidin-5-yl)methyl]-3-methoxyphenol
—— (2-{N'-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-oxo-4,5-dihydro-thiazol-5-yl)-acetic acid 22067-71-6 C12H11N3O4S
(2-{N'-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-oxo-4,5-dihydro-thiazol-5-yl)-acetic acid
—— Pentachlorphenol-Triethylamin-Komplex 6829-43-2 C6HCl5O*C6H15N
Pentachlorphenol-Triethylamin-Komplex
—— N′-(2-hydroxy-4-methoxyphenylmethylidene)-3-pyridincarbohydrazide 118587-38-5 C14H13N3O3
N′-(2-hydroxy-4-methoxyphenylmethylidene)-3-pyridincarbohydrazide
—— {2-[(4-hydroxybenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic acid 21938-64-7 C12H11N3O4S
{2-[(4-hydroxybenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic acid
—— N-(3-hydroxyphenyl)cyanamide 859084-52-9 C7H6N2O
N-(3-hydroxyphenyl)cyanamide
—— 4-isocyanophenol 162471-15-0 C7H5NO
4-isocyanophenol
—— N,N'-bis(4-hydroxy-3-methoxybenzylidene)-1,2-phenylenediamine 73394-80-6 C22H20N2O4
N,N'-bis(4-hydroxy-3-methoxybenzylidene)-1,2-phenylenediamine
—— 2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylamino)methyl)-4-nitrophenol 1174758-52-1 C16H18N2O4
2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylamino)methyl)-4-nitrophenol
—— (4R) 2-(2-hydroxy-4-methoxyphenyl)thiazolidine-4-carboxylic acid 72678-91-2 C11H13NO4S
(4R) 2-(2-hydroxy-4-methoxyphenyl)thiazolidine-4-carboxylic acid
—— 4-<5-(3,4-dimethylisooxazolyl)sulphamyl>-2'-hydroxy-5'-nitrobenzylidene aniline 125186-93-8 C18H16N4O6S
4-<5-(3,4-dimethylisooxazolyl)sulphamyl>-2'-hydroxy-5'-nitrobenzylidene aniline
—— N-(4-hydroxy-3-methoxybenzyl)-6-acetoxy-8-methyl-7-nonenamide 947699-03-8 C20H29NO5
N-(4-hydroxy-3-methoxybenzyl)-6-acetoxy-8-methyl-7-nonenamide