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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
—— 2,4-Dihydroxy-5-methoxymandelsaeure 7298-29-5 C6H12N2*C9H10O6
2,4-Dihydroxy-5-methoxymandelsaeure
—— 2-hydroxy-3-methoxy-5-(2-(trimethylsilyl)ethynyl)benzaldehyde 727375-40-8 C13H16O3Si
2-hydroxy-3-methoxy-5-(2-(trimethylsilyl)ethynyl)benzaldehyde
—— 5-Chloro-2-methyl-4-methylsulfanyl-phenol 101251-04-1 C8H9ClOS
5-Chloro-2-methyl-4-methylsulfanyl-phenol
—— 4-(3-chloro-4-hydroxyphenyl)-1,4-dihydro-2-methyl-6-[2-methyl-5-(trifluoromethyl)-3-furanyl]-3,5-pyridinedicarbonitrile 1033770-62-5 C20H13ClF3N3O2
4-(3-chloro-4-hydroxyphenyl)-1,4-dihydro-2-methyl-6-[2-methyl-5-(trifluoromethyl)-3-furanyl]-3,5-pyridinedicarbonitrile
—— methyl (2Z)-2-(4-hydroxyphenyl)-2-methoxyiminoacetate 66340-55-4 C10H11NO4
methyl (2Z)-2-(4-hydroxyphenyl)-2-methoxyiminoacetate
—— 2-(2-hydroxy-5-methyl-phenyl)-but-3-en-1-ol 104175-26-0 C11H14O2
2-(2-hydroxy-5-methyl-phenyl)-but-3-en-1-ol
—— (4-Hydroxy-3,5-dimethyl-phenyl)-dimethyl-sulfonium 57836-01-8 C10H15OS
(4-Hydroxy-3,5-dimethyl-phenyl)-dimethyl-sulfonium
—— 2-Methoxy-6-pent-1-enylphenol 1187759-59-6 C12H16O2
2-Methoxy-6-pent-1-enylphenol
—— 2-(3,4-dihydroxybenzylideneamino)pyridin-3-ol 1246614-27-6 C12H10N2O3
2-(3,4-dihydroxybenzylideneamino)pyridin-3-ol
—— 2-(5-Pentyl-[1,3,4]oxadiazol-2-yl)-phenol 83431-83-8 C13H16N2O2
2-(5-Pentyl-[1,3,4]oxadiazol-2-yl)-phenol
—— 2-{[(4-bromophenyl)methylene]amino}-4-methylphenol 878193-83-0 C14H12BrNO
2-{[(4-bromophenyl)methylene]amino}-4-methylphenol
—— 1,4-dihydro-4-(4-hydroxy-3-iodophenyl)-2,6-dimethyl-3,5-pyridinedicarbonitrile 1033766-84-5 C15H12IN3O
1,4-dihydro-4-(4-hydroxy-3-iodophenyl)-2,6-dimethyl-3,5-pyridinedicarbonitrile
—— N-(5-Nitro-salicyliden)-2-amino-propan 42551-72-4 C10H12N2O3
N-(5-Nitro-salicyliden)-2-amino-propan
—— 5-(2-ethyl-4,5-dimethoxy-benzyl)-1<i>H</i>-pyrimidine-2,4-dione 6981-19-7 C15H18N2O4
5-(2-ethyl-4,5-dimethoxy-benzyl)-1<i>H</i>-pyrimidine-2,4-dione
—— 2-(3,4-Dihydroxy-benzyl)-1-methyl-pyrrolidin 66162-89-8 C12H17NO2
2-(3,4-Dihydroxy-benzyl)-1-methyl-pyrrolidin
—— 2-(3-allyl-5-chloro-2-hydroxyphenyl)-5-(5-bromothiophen-2-yl)-2,4-dihydro-[1,2,4]triazol-3-one 569689-19-6 C15H11BrClN3O2S
2-(3-allyl-5-chloro-2-hydroxyphenyl)-5-(5-bromothiophen-2-yl)-2,4-dihydro-[1,2,4]triazol-3-one
—— 3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1534369-41-9 C12H16BFO3
3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— 4-[1-(adamantan-2-ylamino)ethyl]benzene-1,3-diol 1157557-41-9 C18H25NO2
4-[1-(adamantan-2-ylamino)ethyl]benzene-1,3-diol
—— 3-nitro-5-(p-nitrophenylsulphonamido)salicylaldehyde azine 84042-28-4 C26H18N8O14S2
3-nitro-5-(p-nitrophenylsulphonamido)salicylaldehyde azine
—— 3-hydroxytyrosyl octyl ether 1156543-96-2 C16H26O3
3-hydroxytyrosyl octyl ether
—— [(2S)-1-[acetyl(propan-2-yl)amino]-3-[4-(2-hydroxyethyl)phenoxy]propan-2-yl] acetate 1312687-84-5 C18H27NO5
[(2S)-1-[acetyl(propan-2-yl)amino]-3-[4-(2-hydroxyethyl)phenoxy]propan-2-yl] acetate
—— 2,5-bis-{[bis-(2-chloro-propyl)-amino]-methyl}-hydroquinone 111799-73-6 C20H32Cl4N2O2
2,5-bis-{[bis-(2-chloro-propyl)-amino]-methyl}-hydroquinone
—— (S)-4-(2-(4-(cycloheptylmethyl)piperazin-1-yl)-3-(methylamino)propyl)phenol 1186220-04-1 C22H37N3O
(S)-4-(2-(4-(cycloheptylmethyl)piperazin-1-yl)-3-(methylamino)propyl)phenol
—— (1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)-N-phenylcyclopentane-1-carboxamide 1427204-49-6 C28H29N3O5
(1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)-N-phenylcyclopentane-1-carboxamide
—— (5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(5-morpholin-4-yl-pentanoyl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-15-6 C42H60N4O9Si
(5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(5-morpholin-4-yl-pentanoyl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— anti-9,17-Dihydroxy<3.2>metacyclophane 143105-70-8 C17H18O2
anti-9,17-Dihydroxy<3.2>metacyclophane
—— 1-but-3-en-1-yl-5-(4-hydroxyphenyl)-2,2-dimethylindan-1-ol 1356058-73-5 C21H24O2
1-but-3-en-1-yl-5-(4-hydroxyphenyl)-2,2-dimethylindan-1-ol
—— 4,5-bis(phenylethynyl)-2-methoxyphenol 108213-91-8 C23H16O2
4,5-bis(phenylethynyl)-2-methoxyphenol
—— Sulfurous acid bis-(5-bromo-2-hydroxy-benzyl) ester 62896-67-7 C14H12Br2O5S
Sulfurous acid bis-(5-bromo-2-hydroxy-benzyl) ester
—— 2,3-dibutylthio-4-(2-nitroethylene)-phenol 157458-11-2 C17H25NO4S2
2,3-dibutylthio-4-(2-nitroethylene)-phenol
—— 11-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-undecanoic acid 4-(4S,7R,8S,9S,13Z,16S)-[7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yloxycarbonyloxymethyl]-2-nitro-phenyl ester 658054-60-5 C59H81N3O13SSi
11-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-undecanoic acid 4-(4S,7R,8S,9S,13Z,16S)-[7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yloxycarbonyloxymethyl]-2-nitro-phenyl ester
—— 2-Chloro-4-methylsulfanyl-6-nitro-phenol 32279-01-9 C7H6ClNO3S
2-Chloro-4-methylsulfanyl-6-nitro-phenol
—— 2-(Di-prop-2-ynyl-amino)-5-methyl-phenol 23478-19-5 C13H13NO
2-(Di-prop-2-ynyl-amino)-5-methyl-phenol
—— 2-Methoxy-6-tropyl-phenol 5726-15-8 C14H14O2
2-Methoxy-6-tropyl-phenol
—— 3,5-Dimethyl-4-hydroxy-benzoldiazoniumchlorid 1075-53-2 C8H9N2O*Cl
3,5-Dimethyl-4-hydroxy-benzoldiazoniumchlorid
—— 2-Cyclopent-2-enyl-benzene-1,3-diol 57878-38-3 C11H12O2
2-Cyclopent-2-enyl-benzene-1,3-diol
—— N,N'-di(2-hydroxy-5-nitrobenzyl)-1,3-propanediamine-N,N'-diacetic acid 63651-95-6 C21H24N4O10
N,N'-di(2-hydroxy-5-nitrobenzyl)-1,3-propanediamine-N,N'-diacetic acid
—— 4-(2-(2-hydroxyethyl)-3-methylbut-3-en-1-yl)phenol 1346619-67-7 C13H18O2
4-(2-(2-hydroxyethyl)-3-methylbut-3-en-1-yl)phenol
—— 5-(3-Methoxy-4-hydroxyphenyl)-4,4-dimethyl-2,4-dihydropyrazol-3-one 1093857-87-4 C12H14N2O3
5-(3-Methoxy-4-hydroxyphenyl)-4,4-dimethyl-2,4-dihydropyrazol-3-one
—— 4-Chloro-3,5-diethyl-phenol 38730-62-0 C10H13ClO
4-Chloro-3,5-diethyl-phenol
—— 1-(p-Hydroxyphenyl)-2-nitro-hexen 1921-77-3 C12H15NO3
1-(p-Hydroxyphenyl)-2-nitro-hexen
—— 2,3-dibromo-6-nitro-phenol 858854-85-0 C6H3Br2NO3
2,3-dibromo-6-nitro-phenol
—— α-(5-Chlor-2-hydroxybenzyliden)-γ-butyrolacton 1208-49-7 C11H9ClO3
α-(5-Chlor-2-hydroxybenzyliden)-γ-butyrolacton
—— Picric acid; compound with 2-amino-1-phenyl-5,6-dihydro-1H-pyrimidin-4-one 100185-46-4 C6H3N3O7*C10H11N3O
Picric acid; compound with 2-amino-1-phenyl-5,6-dihydro-1H-pyrimidin-4-one
—— N-Methyl-formidiniumsaeure-methylester-pikrat 3619-31-6 C3H7NO*C6H3N3O7
N-Methyl-formidiniumsaeure-methylester-pikrat
—— [Lu(N,N'-bis[(6-carboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6(-2H))](1+) 1162111-55-8 C26H34LuN4O8
[Lu(N,N'-bis[(6-carboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6(-2H))](1+)
—— 1421330-76-8 C10H10Br2N2O
—— 4-(3-chloro-4-hydroxyphenyl)-1,4-dihydro-2-(3-hydroxyphenyl)-6-methyl-3,5-pyridinedicarbonitrile 1033770-56-7 C20H14ClN3O2
4-(3-chloro-4-hydroxyphenyl)-1,4-dihydro-2-(3-hydroxyphenyl)-6-methyl-3,5-pyridinedicarbonitrile
—— 2-bromo-1-(3-bromo-4-hydroxy-5-methoxy-phenyl)-propan-1-ol 90869-37-7 C10H12Br2O3
2-bromo-1-(3-bromo-4-hydroxy-5-methoxy-phenyl)-propan-1-ol
—— 2-[2′-(5-nitrothiazolyl)azo]-4-methoxyphenol 16247-79-3 C10H8N4O4S
2-[2′-(5-nitrothiazolyl)azo]-4-methoxyphenol