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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-ethyl-6-methyl-hydroquinone 72693-14-2 C9H12O2
2-ethyl-6-methyl-hydroquinone
—— 5-(O-ethylthiocarboxy)-3-hydroxy-4-methoxybenzaldehyde 80547-70-2 C11H12O4S2
5-(O-ethylthiocarboxy)-3-hydroxy-4-methoxybenzaldehyde
—— 2-fluoro-4-hydroxybenzothioamide 1174738-05-6 C7H6FNOS
2-fluoro-4-hydroxybenzothioamide
—— 3-fluoro-4-(methylsulfonylmethyl)phenol 1037776-17-2 C8H9FO3S
3-fluoro-4-(methylsulfonylmethyl)phenol
—— methyl 3-(4-fluoro-2-hydroxyphenyl)propanoate 936327-90-1 C10H11FO3
methyl 3-(4-fluoro-2-hydroxyphenyl)propanoate
—— 2,2-dimethyl-propionic acid 4-{2-[2-chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-ethyl}-phenyl ester 890042-59-8 C23H25ClN2O4
2,2-dimethyl-propionic acid 4-{2-[2-chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-ethyl}-phenyl ester
—— 5-(3-chloro-4-hydroxyphenyl)-3-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 617688-89-8 C18H13ClO3S
5-(3-chloro-4-hydroxyphenyl)-3-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde
—— 3-(5-Hydroxy-2-methylphenyl)-5-(4-hydroxyphenyl)-4-methyl-2-thiophenecarbaldehyde 617688-80-9 C19H16O3S
3-(5-Hydroxy-2-methylphenyl)-5-(4-hydroxyphenyl)-4-methyl-2-thiophenecarbaldehyde
—— 2-chloro-3,5-dimethoxy-4-methylphenol 39024-70-9 C9H11ClO3
2-chloro-3,5-dimethoxy-4-methylphenol
—— 2,1-benzisoxazol-7-ol 1001434-71-4 C7H5NO2
2,1-benzisoxazol-7-ol
—— 3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 617688-83-2 C18H13ClO3S
3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde
—— 2,3-(3-hydroxyocta-1,7-diyne-1,8-diyl)-5,6-dimethylhydroquinone 144182-11-6 C16H16O3
2,3-(3-hydroxyocta-1,7-diyne-1,8-diyl)-5,6-dimethylhydroquinone
—— 2-bromo-6-(tert-butyldimethylsilyl)-4-methylphenol 154345-35-4 C13H21BrOSi
2-bromo-6-(tert-butyldimethylsilyl)-4-methylphenol
—— 2-fluoro-4-[5-(3-hydroxyphenyl)-3-thienyl]phenol 1193525-06-2 C16H11FO2S
2-fluoro-4-[5-(3-hydroxyphenyl)-3-thienyl]phenol
—— Formaldehyde;naphthalene-2,7-diol;phenol 26936-19-6 C17H16O4
Formaldehyde;naphthalene-2,7-diol;phenol
—— 2-Fluoro-4-[5-(3-hydroxyphenyl)-2-thienyl]phenol 1122660-29-0 C16H11FO2S
2-Fluoro-4-[5-(3-hydroxyphenyl)-2-thienyl]phenol
—— 2-(3-hydroxyphenyl)-2-isopropoxy-1,1-diisopropylethene 172024-41-8 C17H26O2
2-(3-hydroxyphenyl)-2-isopropoxy-1,1-diisopropylethene
—— benzyl 3-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylpropionate 1030600-31-7 C26H35NO7
benzyl 3-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylpropionate
—— benzyl 4-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylbutyrate 1030600-34-0 C27H37NO7
benzyl 4-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylbutyrate
—— 2-{3-bromo-5-(trimethylsilyl)-4-[(trimethylsilyl)oxy]phenyl}ethyl methanesulfonate 1127943-39-8 C15H27BrO4SSi2
2-{3-bromo-5-(trimethylsilyl)-4-[(trimethylsilyl)oxy]phenyl}ethyl methanesulfonate
—— (3-bromo-2-[(trimethylsilyl)oxy]-5-{2-[(trimethylsilyl)oxy]ethyl}phenyl)(trimethyl)silane 1127943-34-3 C17H33BrO2Si3
(3-bromo-2-[(trimethylsilyl)oxy]-5-{2-[(trimethylsilyl)oxy]ethyl}phenyl)(trimethyl)silane
—— (6'R)-4-hydroxy-3-methoxy-5-(3',7'-dimethyl-6',7'-epoxy-2'-octenyl)benzyl alcohol 844868-76-4 C18H26O4
(6'R)-4-hydroxy-3-methoxy-5-(3',7'-dimethyl-6',7'-epoxy-2'-octenyl)benzyl alcohol
—— 4-chloro-2-fluoro-6-nitrophenol 58348-99-5 C6H3ClFNO3
4-chloro-2-fluoro-6-nitrophenol
—— 2-(2-hydroxy-3-nitrophenyl)-N-(trifluoroacetyl)ethylamine 108773-05-3 C10H9F3N2O4
2-(2-hydroxy-3-nitrophenyl)-N-(trifluoroacetyl)ethylamine
—— N-[1-(4-hydroxy-3-fluoro-phenyl)-ethyl]-acetamide 1443670-63-0 C10H12FNO2
N-[1-(4-hydroxy-3-fluoro-phenyl)-ethyl]-acetamide
—— 2-(3-methylenepentyl)phenol 51082-22-5 C12H16O
2-(3-methylenepentyl)phenol
—— 2-(2-Hydroxy-5-chlor-phenyl)-thiazolidin 78760-47-1 C9H10ClNOS
2-(2-Hydroxy-5-chlor-phenyl)-thiazolidin
—— 3,4-diiodo-phenol 1243476-86-9 C6H4I2O
3,4-diiodo-phenol
—— 2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole 1300713-17-0 C15H12N4O4S
2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole
—— Ethanol, 2-(1-benzimidazolylmethoxy)-, picrate 34703-78-1 C16H15N5O9
Ethanol, 2-(1-benzimidazolylmethoxy)-, picrate
—— 2-(2-Hydroxy-5-methyl-phenyl)-thiazolidin 78760-56-2 C10H13NOS
2-(2-Hydroxy-5-methyl-phenyl)-thiazolidin
—— 5-(2-Hydroxyphenyl)-2-propan-2-ylimino-1,3-thiazolidin-4-one 1628629-69-5 C12H14N2O2S
5-(2-Hydroxyphenyl)-2-propan-2-ylimino-1,3-thiazolidin-4-one
—— 3'-methoxy-4'-hydroxy-N-methylacetanilide 102683-60-3 C10H13NO3
3'-methoxy-4'-hydroxy-N-methylacetanilide
—— 2-(3-hydroxyphenyl)-3-ethoxycarbonyl-2,5-dihydrofuran 1041333-74-7 C13H14O4
2-(3-hydroxyphenyl)-3-ethoxycarbonyl-2,5-dihydrofuran
—— (Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-3-hexyl-2-isopropylimino-thiazolidin-4-one 1228116-87-7 C19H25ClN2O2S
(Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-3-hexyl-2-isopropylimino-thiazolidin-4-one
—— 1146684-92-5 C46H40N6O10S2
—— N,N'-(1,2-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide) 1146684-93-6 C46H40N6O10S2
N,N'-(1,2-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide)
—— 2,5-dibromo-3,6-dimethylbenzene-1,4-diol 848320-35-4 C8H8Br2O2
2,5-dibromo-3,6-dimethylbenzene-1,4-diol
—— 1-(4-hydroxyphenyl)-2-(3-pyridyl)ethane 85666-07-5 C13H13NO
1-(4-hydroxyphenyl)-2-(3-pyridyl)ethane
—— 4-(2-hydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 1269025-34-4 C16H21NO3
4-(2-hydroxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
—— (Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-isopropylimino-3-phenethyl-thiazolidin-4-one 1228117-07-4 C21H21ClN2O2S
(Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-isopropylimino-3-phenethyl-thiazolidin-4-one
—— 4-ethylthio-3-hydroxynitrobenzene 146310-47-6 C8H9NO3S
4-ethylthio-3-hydroxynitrobenzene
—— 5-formyl-4-hydroxy-3-methoxy-2-(methylthio)benzonitrile 1245744-75-5 C10H9NO3S
5-formyl-4-hydroxy-3-methoxy-2-(methylthio)benzonitrile
—— 2-hydroxy-1-methoxy-3-<2-((methoxycarbonyl)amino)ethyl>benzene 141849-19-6 C11H15NO4
2-hydroxy-1-methoxy-3-<2-((methoxycarbonyl)amino)ethyl>benzene
—— 5-acetyl-1-(3,4-dimethoxy-2-hydroxyphenethyl)-2-piperidinone 89680-95-5 C17H23NO5
5-acetyl-1-(3,4-dimethoxy-2-hydroxyphenethyl)-2-piperidinone
—— 5,5-dimethyl-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene 116911-86-5 C16H24O3
5,5-dimethyl-6-(3',5'-dimethoxy-4'-hydroxyphenyl)-1-hexene
—— 4-(3,5-dimethoxy-4-hydroxyphenyl)-1-butene 112468-44-7 C12H16O3
4-(3,5-dimethoxy-4-hydroxyphenyl)-1-butene
—— 2,6-dimethoxy-4-((tetrahydro-2H-pyran-2-yloxy)methyl)phenol 1443015-26-6 C14H20O5
2,6-dimethoxy-4-((tetrahydro-2H-pyran-2-yloxy)methyl)phenol
—— (E)-4-methyl-2-(prop-1-enyl)phenol 65001-69-6 C10H12O
(E)-4-methyl-2-(prop-1-enyl)phenol
—— 3-(2-(4-Hydroxyphenyl)ethyl)sydnone imine monohydrochloride 37744-03-9 C10H12ClN3O2
3-(2-(4-Hydroxyphenyl)ethyl)sydnone imine monohydrochloride