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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
—— tert-butyl {2-[4-hydroxy-2-(hydroxymethyl)-6-methylphenoxy]-1-methylethyl}carbamate 1237512-82-1 C16H25NO5
tert-butyl {2-[4-hydroxy-2-(hydroxymethyl)-6-methylphenoxy]-1-methylethyl}carbamate
—— Ni(HASc)2Cl2 140621-99-4 C18H22Cl2N6NiO4
Ni(HASc)2Cl2
—— 4-[(Z)-(4-ethyl-3,5-dimethylpyrrol-2-ylidene)methyl]-2-methoxyphenol;hydrobromide 16176-29-7 C16H20BrNO2
4-[(Z)-(4-ethyl-3,5-dimethylpyrrol-2-ylidene)methyl]-2-methoxyphenol;hydrobromide
—— 13936-84-0 C22H26F2N2O2
—— 1-[3-(2-Hydroxy-phenyl)-5,7-diphenyl-3,3a,4,7-tetrahydro-pyrazolo[4,3-e][1,2,4]triazin-2-yl]-ethanone 82059-78-7 C24H21N5O2
1-[3-(2-Hydroxy-phenyl)-5,7-diphenyl-3,3a,4,7-tetrahydro-pyrazolo[4,3-e][1,2,4]triazin-2-yl]-ethanone
—— (S)-4-{2-[2-hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl}phenoxymethyl-n-hexylphosphinic acid, n-butyl ester 177704-91-5 C28H44NO6P
(S)-4-{2-[2-hydroxy-3-(4-hydroxyphenoxy)propylamino]ethyl}phenoxymethyl-n-hexylphosphinic acid, n-butyl ester
—— 2-(2-Hydroxy-5-nitro-phenyl)-N-methyl-acetamide 912948-23-3 C9H10N2O4
2-(2-Hydroxy-5-nitro-phenyl)-N-methyl-acetamide
—— 2-(o-hydroxyphenyliminomethyl)pyridine N-oxide 173349-50-3 C12H10N2O2
2-(o-hydroxyphenyliminomethyl)pyridine N-oxide
—— 2-cyclopropyl-4-fluorophenol 1232774-27-4 C9H9FO
2-cyclopropyl-4-fluorophenol
—— 2-(Methanesulfonylmethyl)phenol 53380-29-3 C8H10O3S
2-(Methanesulfonylmethyl)phenol
—— 2,6-Dibrom-5-chlor-vanillin, 2.6-Dibrom-5-chlor-4-hydroxy-3-methoxy-benzaldehyd 90001-47-1 C8H5Br2ClO3
2,6-Dibrom-5-chlor-vanillin, 2.6-Dibrom-5-chlor-4-hydroxy-3-methoxy-benzaldehyd
—— N-[1-(2-fluoro-4-hydroxyphenyl)ethyl]acetamide 1594129-58-4 C10H12FNO2
N-[1-(2-fluoro-4-hydroxyphenyl)ethyl]acetamide
—— 4-[1,1-Bis(ethylsulfanyl)ethyl]phenol 77503-08-3 C12H18OS2
4-[1,1-Bis(ethylsulfanyl)ethyl]phenol
—— gelsevanillidine 1160934-44-0 C27H28N2O5
gelsevanillidine
—— 2-Methyl-6-[[2,4,6-triethyl-3-[(2-hydroxy-3-methylphenyl)methylideneamino]phenyl]iminomethyl]phenol 927894-95-9 C28H32N2O2
2-Methyl-6-[[2,4,6-triethyl-3-[(2-hydroxy-3-methylphenyl)methylideneamino]phenyl]iminomethyl]phenol
—— Einecs 287-268-4 85455-34-1 C24H37CrN4O11S+
Einecs 287-268-4
—— 4-[5-ethyl-4-(4-hydroxyphenyl)furan-3-yl]phenol 132589-93-6 C18H16O3
4-[5-ethyl-4-(4-hydroxyphenyl)furan-3-yl]phenol
—— N-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]-2-methylfuran-3-carboxamide 304906-07-8 C14H14N2O4
N-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]-2-methylfuran-3-carboxamide
—— 2-(2,6-Dichloro-3-hydroxyphenyl)acetic acid 89894-48-4 C8H6Cl2O3
2-(2,6-Dichloro-3-hydroxyphenyl)acetic acid
—— <i>N</i>-(5-bromo-thiazol-2-yl)-2-hydroxy-5-nitro-benzamide 74688-64-5 C10H6BrN3O4S
<i>N</i>-(5-bromo-thiazol-2-yl)-2-hydroxy-5-nitro-benzamide
—— 2-[(2-Butynoxyimino)methyl]-4-fluoro-3-methylphenol 103743-29-9 C12H12FNO2
2-[(2-Butynoxyimino)methyl]-4-fluoro-3-methylphenol
—— 182356-63-4 C12H11NO7
—— 6-(2-hydroxy-phenyl)-2-methyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one 56924-62-0 C11H12N2O2
6-(2-hydroxy-phenyl)-2-methyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one
—— 15,35,55,75-tetrakis((4-hydroxy-3-methoxybenzylidene)amino)-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,32,52,72-tetraol 1278534-08-9 C60H52N4O12
15,35,55,75-tetrakis((4-hydroxy-3-methoxybenzylidene)amino)-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,32,52,72-tetraol
—— 6-(3-Amino-1-ethyl-propyl)-3-(α-cyclopropyl-meta-aminobenzyl)-4-hydroxy-pyran-2-one 174485-12-2 C20H26N2O3
6-(3-Amino-1-ethyl-propyl)-3-(α-cyclopropyl-meta-aminobenzyl)-4-hydroxy-pyran-2-one
—— 2-(3,4-Dihydroxyphenaethyl)-5,6,7,8-tetrahydro-3-hydroxynaphthochinon-(1,4) 93878-69-4 C18H18O5
2-(3,4-Dihydroxyphenaethyl)-5,6,7,8-tetrahydro-3-hydroxynaphthochinon-(1,4)
—— 6-Heptadecyl-3-methoxy-2-methyl-phenol 856182-11-1 C25H44O2
6-Heptadecyl-3-methoxy-2-methyl-phenol
—— 2-((E)-2,6-Bis-benzyloxy-hex-4-enyl)-4,5-dimethoxy-phenol 143653-82-1 C28H32O5
2-((E)-2,6-Bis-benzyloxy-hex-4-enyl)-4,5-dimethoxy-phenol
—— 2-(2-methyl-5-phenyl-5H-isoxazolo[2,3-a]pyrimidin-7-yl)phenol 1260673-03-7 C19H16N2O2
2-(2-methyl-5-phenyl-5H-isoxazolo[2,3-a]pyrimidin-7-yl)phenol
—— 2-(2-hydroxyphenyl)-2-oxazoline hydrochloride 24201-18-1 C9H9NO2*ClH
2-(2-hydroxyphenyl)-2-oxazoline hydrochloride
—— 5-[1-(6-bromohexyl)cyclopentyl]benzene-1,3-diol 941583-90-0 C17H25BrO2
5-[1-(6-bromohexyl)cyclopentyl]benzene-1,3-diol
—— N-[3-([(tert-butoxy)carbonyl](4-{[(tert-butoxy)carbonyl]amino}butyl)amino)propyl]-3-(2-hydroxyphenyl)propanamide 350609-85-7 C26H43N3O6
N-[3-([(tert-butoxy)carbonyl](4-{[(tert-butoxy)carbonyl]amino}butyl)amino)propyl]-3-(2-hydroxyphenyl)propanamide
—— 2-butyl-5,6-dimethylresorcinol 1006058-02-1 C12H18O2
2-butyl-5,6-dimethylresorcinol
—— 5-Isobutylamino-2-methyl-phenol 104179-06-8 C11H17NO
5-Isobutylamino-2-methyl-phenol
—— 2-(1,3-dimethylbutyl)phenol 91763-72-3 C12H18O
2-(1,3-dimethylbutyl)phenol
—— 3-(3,5-Dibromo-2-hydroxy-4-methoxy-phenyl)-2-[(E)-hydroxyimino]-propionic acid ethyl ester 114114-05-5 C12H13Br2NO5
3-(3,5-Dibromo-2-hydroxy-4-methoxy-phenyl)-2-[(E)-hydroxyimino]-propionic acid ethyl ester
—— 1-isopropylamino-3-(4-hydroxy-2-N-methylcarbamoylmethoxyphenoxy)-propan-2-ol 34920-15-5 C15H24N2O5
1-isopropylamino-3-(4-hydroxy-2-N-methylcarbamoylmethoxyphenoxy)-propan-2-ol
—— 2-{[azepan-1-yl(ethyl)amino]methyl}-6-methoxyphenol 746597-05-7 C16H26N2O2
2-{[azepan-1-yl(ethyl)amino]methyl}-6-methoxyphenol
—— 4-(1-furan-2-yl-2-hydroxyethyl)-3-methylphenol 1073131-79-9 C13H14O3
4-(1-furan-2-yl-2-hydroxyethyl)-3-methylphenol
—— (2,2'-Dihydroxy-benzil)-dibenzaldehyd-azin, Salicil-dibenzaldehyd-azin 102924-50-5 C28H22N4O2
(2,2'-Dihydroxy-benzil)-dibenzaldehyd-azin, Salicil-dibenzaldehyd-azin
—— N,N'-bis(2-hydroxy-3-methoxy-benzylidene)-1,3-diaminobenzene 1030937-62-2 C22H20N2O4
N,N'-bis(2-hydroxy-3-methoxy-benzylidene)-1,3-diaminobenzene
—— 2-Oxo-6-<4-hydroxy-3,5-dimethyl-phenyl>-hexahydropyrimidin 105336-90-1 C12H16N2O2
2-Oxo-6-<4-hydroxy-3,5-dimethyl-phenyl>-hexahydropyrimidin
—— 5-Chlor-6-brom-2-amino-vanillin 90050-44-5 C8H7BrClNO3
5-Chlor-6-brom-2-amino-vanillin
—— 3-hydroxy-4-methoxy-benzaldehyde 4-(1(2)<i>H</i>-indazol-6-yl)-thiosemicarbazone 22497-26-3 C16H15N5O2S
3-hydroxy-4-methoxy-benzaldehyde 4-(1(2)<i>H</i>-indazol-6-yl)-thiosemicarbazone
—— (E,E)-2-thioacetaminocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile 368836-84-4 C14H14N2O3S
(E,E)-2-thioacetaminocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile
—— 4-(Hydroxyimino)-4-(2-hydroxy-5-methylphenyl)butanoic acid 178462-00-5 C11H13NO4
4-(Hydroxyimino)-4-(2-hydroxy-5-methylphenyl)butanoic acid
—— N-(3-bromo-5-methylsalicylidene)-3-[bis(5-methyl-2-furyl)methyl]aniline 1000414-97-0 C25H22BrNO3
N-(3-bromo-5-methylsalicylidene)-3-[bis(5-methyl-2-furyl)methyl]aniline
—— 5-Nitro-2-hydroxy-benzal-ethylheptylhydrazin 88564-90-3 C16H25N3O3
5-Nitro-2-hydroxy-benzal-ethylheptylhydrazin
—— 4-(5-chloropyridin-2-yl)-3,5-bis((triethylsilyl)ethynyl)phenol 1581719-41-6 C27H36ClNOSi2
4-(5-chloropyridin-2-yl)-3,5-bis((triethylsilyl)ethynyl)phenol
—— 2-[(E)-(5-aminotetrazol-1-yl)iminomethyl]phenol 321725-55-7 C8H8N6O
2-[(E)-(5-aminotetrazol-1-yl)iminomethyl]phenol