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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-(6-methyl-1,2,4,5-tetrazin-3-yl)phenol 58884-35-8 C9H8N4O
4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenol
—— 2-deuterio-4-methoxyphenol 80234-08-8 C7H8O2
2-deuterio-4-methoxyphenol
—— 1-(2-Hydroxyphenyl)undec-3-yn-5-yl acetate 1329465-49-7 C19H26O3
1-(2-Hydroxyphenyl)undec-3-yn-5-yl acetate
—— N-Isopropyl-5-(3,4-dihydroxy-5-nitrophenyl)pentanoic amide 116313-80-5 C14H20N2O5
N-Isopropyl-5-(3,4-dihydroxy-5-nitrophenyl)pentanoic amide
—— N-(4-{[1-(4-Hydroxy-3-iodo-5-methoxy-phenyl)-meth-(E)-ylidene]-amino}-phenyl)-acetamide 124314-61-0 C16H15IN2O3
N-(4-{[1-(4-Hydroxy-3-iodo-5-methoxy-phenyl)-meth-(E)-ylidene]-amino}-phenyl)-acetamide
—— 3-(4-Bromo-2-chloro-5-methylphenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one 186647-73-4 C16H16BrClO3
3-(4-Bromo-2-chloro-5-methylphenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one
—— 2-(4-Hydroxybenzylidenhydrazono)-4-oxo-3,5-diphenyl-thiazolidin 106410-41-7 C22H17N3O2S
2-(4-Hydroxybenzylidenhydrazono)-4-oxo-3,5-diphenyl-thiazolidin
—— N-(4-chlorophenyl)-N-hydroxy-2-[(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylhydrazinylidene]propanimidamide 126389-84-2 C16H15ClN4O3
N-(4-chlorophenyl)-N-hydroxy-2-[(2-hydroxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylhydrazinylidene]propanimidamide
—— (2R,3R,4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-[(5-methoxy-2-hydroxyphenyl)amino]-2H-1-benzopyran 804560-24-5 C20H24N2O8
(2R,3R,4S)-6-nitro-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-[(5-methoxy-2-hydroxyphenyl)amino]-2H-1-benzopyran
—— disodium resorcinolate 6025-45-2 C6H4O2*2Na
disodium resorcinolate
—— 5-bromosalicylaldehyde heptanoylhydrazone 402953-19-9 C14H19BrN2O2
5-bromosalicylaldehyde heptanoylhydrazone
—— 4-{4-(azidomethyldimethylsilanyl)-1,1-bis-[3-(azidomethyldimethylsilanyl)propyl]butyl}phenol 387339-01-7 C25H47N9OSi3
4-{4-(azidomethyldimethylsilanyl)-1,1-bis-[3-(azidomethyldimethylsilanyl)propyl]butyl}phenol
—— Sodium 3,6-dihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methyl-2-buten-1-yl)-5-oxo-1,3-cyclohexadien-1-olate 6202-38-6 C21H29NaO5
Sodium 3,6-dihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methyl-2-buten-1-yl)-5-oxo-1,3-cyclohexadien-1-olate
—— 2-(N',N'-dimethylformamidino) phenol 116024-41-0 C9H12N2O
2-(N',N'-dimethylformamidino) phenol
—— 4-(4-Hydroxy-3,5-dimethylphenyl)butanal 1005008-16-1 C12H16O2
4-(4-Hydroxy-3,5-dimethylphenyl)butanal
—— (E)-1-Cyano-2-(4-hydroxy-phenyl)-ethenesulfonic acid amide 41827-60-5 C9H8N2O3S
(E)-1-Cyano-2-(4-hydroxy-phenyl)-ethenesulfonic acid amide
—— 2-hydroxy-N-(p-tolylmethyl)benzenecarbothioamide 1132646-07-1 C15H15NOS
2-hydroxy-N-(p-tolylmethyl)benzenecarbothioamide
—— 5,6,30,31-tetrahydroxy-2,11,27,36-tetramethyl-2,11,27,36-tetraaza<3.3.1-3.3.1>paracyclophane-3,10,28,35-tetraone 145731-75-5 C50H48N4O8
5,6,30,31-tetrahydroxy-2,11,27,36-tetramethyl-2,11,27,36-tetraaza<3.3.1-3.3.1>paracyclophane-3,10,28,35-tetraone
—— (2Z,5Z)-2-[(4-hydroxy-2-methylphenyl)azamethylene]-5-({2-[(3-(1-pyrrolidinyl)propyl)amino](1,3-thiazol-5-yl)}methylene)-1,3-thiazolidin-4-one 1253208-74-0 C21H25N5O2S2
(2Z,5Z)-2-[(4-hydroxy-2-methylphenyl)azamethylene]-5-({2-[(3-(1-pyrrolidinyl)propyl)amino](1,3-thiazol-5-yl)}methylene)-1,3-thiazolidin-4-one
—— 2-Cyano-3-(4-hydroxy-2,3,5-trimethyl-phenyl)-but-2-enedinitrile 138385-50-9 C14H11N3O
2-Cyano-3-(4-hydroxy-2,3,5-trimethyl-phenyl)-but-2-enedinitrile
—— 4-(pyridin-3-ylmethyl)benzene-1,3-diol 1206192-92-8 C12H11NO2
4-(pyridin-3-ylmethyl)benzene-1,3-diol
—— hydroquinone benzoquinonephosphate 94583-98-9 C6H4O2*C6H6O2*H3O4P
hydroquinone benzoquinonephosphate
—— 2-(3,4-Dihydroxy-5-methoxyphenyl)-2,2-dimethoxyacetonitrile 1000180-47-1 C11H13NO5
2-(3,4-Dihydroxy-5-methoxyphenyl)-2,2-dimethoxyacetonitrile
—— 4-(1,4,5-Trimethyl-1,2,3,6-tetrahydro-pyridin-2-ylmethyl)-phenol 66170-80-7 C15H21NO
4-(1,4,5-Trimethyl-1,2,3,6-tetrahydro-pyridin-2-ylmethyl)-phenol
—— 2-(hydroxy-{[2-(hydroxyphenyl)methylene]amino}methyl)phenol 882426-52-0 C14H13NO3
2-(hydroxy-{[2-(hydroxyphenyl)methylene]amino}methyl)phenol
—— 1-Cyclohexyl-4-<4-hydroxy-phenyl>-butan-2-on 1760-63-0 C16H22O2
1-Cyclohexyl-4-<4-hydroxy-phenyl>-butan-2-on
—— 4-(hydroxymethyl)-3,6-dimethyl-2-nitrophenol 79755-31-0 C9H11NO4
4-(hydroxymethyl)-3,6-dimethyl-2-nitrophenol
—— 1186297-26-6 C36H40N4NiO5
—— dodecyl hydrogen sulfate;4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol 75744-81-9 C21H39NO7S
dodecyl hydrogen sulfate;4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
—— 2-bromo-1-[5-(2-hydroxy-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethanone 60640-60-0 C11H10BrNO3
2-bromo-1-[5-(2-hydroxy-phenyl)-4,5-dihydro-isoxazol-3-yl]-ethanone
—— <4-Hydroxy-3-methoxy-benzyliden>-4-rhodan-anilin 3378-53-8 C15H12N2O2S
<4-Hydroxy-3-methoxy-benzyliden>-4-rhodan-anilin
—— 41350-44-1 C20H16N2O2S2
—— Cyclobutanecarboxylic acid, 1-(3-chloro-6-fluoro-2-hydroxyphenyl)- 1314714-47-0 C11H10ClFO3
Cyclobutanecarboxylic acid, 1-(3-chloro-6-fluoro-2-hydroxyphenyl)-
—— 3-ethyl-2,4,6-trihydroxy-benzaldehyde 412021-94-4 C9H10O4
3-ethyl-2,4,6-trihydroxy-benzaldehyde
—— 4-Allyl-3-methyl-benzene-1,2-diol 53877-55-7 C10H12O2
4-Allyl-3-methyl-benzene-1,2-diol
—— 2-(azepan-1-ylimino-methyl)-phenol 16987-32-9 C13H18N2O
2-(azepan-1-ylimino-methyl)-phenol
—— 6-dodecyl-6-(4-hydroxy-3,5-dinitrobenzyl)-1,4,8,11-tetraoxacyclotetradecane 106419-28-7 C29H48N2O9
6-dodecyl-6-(4-hydroxy-3,5-dinitrobenzyl)-1,4,8,11-tetraoxacyclotetradecane
—— O-Ethoxycarbonyl-4-hydroxynbenzaldoxime 174633-92-2 C10H11NO4
O-Ethoxycarbonyl-4-hydroxynbenzaldoxime
—— 1374156-39-4 C15H17NO2
—— 4-[(2-hydroxy-5-nitrophenyl)diazenyl]-2-methyl-5-propyl-4H-pyrazol-3-one 1210911-83-3 C13H15N5O4
4-[(2-hydroxy-5-nitrophenyl)diazenyl]-2-methyl-5-propyl-4H-pyrazol-3-one
—— 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene-1,3-diol 844501-21-9 C12H17BO4
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene-1,3-diol
—— 5-amino-3-benzyl-4-(4-hydroxy-3-methoxy-phenyl)-[1,2,3]oxadiazolium betaine 5082-75-7 C16H15N3O3
5-amino-3-benzyl-4-(4-hydroxy-3-methoxy-phenyl)-[1,2,3]oxadiazolium betaine
—— 5-(3,4-dihydroxy-benzylidene)-imidazolidine-2,4-dithione 99361-41-8 C10H8N2O2S2
5-(3,4-dihydroxy-benzylidene)-imidazolidine-2,4-dithione
—— 2-amino-4-(2-fluoro-4-hydroxyphenylamino)pyridine 139425-53-9 C11H10FN3O
2-amino-4-(2-fluoro-4-hydroxyphenylamino)pyridine
—— 2,5-Difluoro-4-hydroxyphenylboronic acid pinacol ester 1817835-85-0 C12H15BF2O3
2,5-Difluoro-4-hydroxyphenylboronic acid pinacol ester
—— (3R*,4S*)-3-carboxymethyl-4-(4-hydroxyphenyl)-4-methylcyclohexan-1-one 99432-92-5 C15H18O4
(3R*,4S*)-3-carboxymethyl-4-(4-hydroxyphenyl)-4-methylcyclohexan-1-one
—— 4,4'-(6-phenyl-1,3,5-triazine-2,4-diyl)bis(benzene-1,3-diol) 2125-25-9 C21H15N3O4
4,4'-(6-phenyl-1,3,5-triazine-2,4-diyl)bis(benzene-1,3-diol)
—— 3-Amino-5-(2-hydroxyphenyl)-1,2-oxazole-4-carboxamide 1092534-32-1 C10H9N3O3
3-Amino-5-(2-hydroxyphenyl)-1,2-oxazole-4-carboxamide
—— 2-Methyl-4-(4-piperidin-1-yl-butylsulfanyl)-phenol 123192-64-3 C16H25NOS
2-Methyl-4-(4-piperidin-1-yl-butylsulfanyl)-phenol
—— 3-chloro-2-hydroxy-benzaldehyde-semicarbazone 67810-64-4 C8H8ClN3O2
3-chloro-2-hydroxy-benzaldehyde-semicarbazone