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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 3-hydroxyphenethyl(isopropyl)carbamate 1446332-95-1 C16H25NO3
tert-butyl 3-hydroxyphenethyl(isopropyl)carbamate
—— N-methyl-N-[2-(2,4,6-tribromo-3-hydroxyphenyl)ethyl]formamide 293756-94-2 C10H10Br3NO2
N-methyl-N-[2-(2,4,6-tribromo-3-hydroxyphenyl)ethyl]formamide
—— (3-hydroxy-4-nitro-phenyl)-acetic acid ethyl ester 288580-52-9 C10H11NO5
(3-hydroxy-4-nitro-phenyl)-acetic acid ethyl ester
—— 6,7,8,9-tetrahydro-5H-benzo[7]annulene-2,5-diol 1382491-03-3 C11H14O2
6,7,8,9-tetrahydro-5H-benzo[7]annulene-2,5-diol
—— 3-hydroxyphenylacetic acid N-hydroxysuccinimidyl ester 186370-90-1 C12H11NO5
3-hydroxyphenylacetic acid N-hydroxysuccinimidyl ester
—— 3,6-diethyl-N-(1-ethylpropyl)-5-(2-hydroxy-4-methoxyphenyl)pyrazin-2-amine 355835-57-3 C20H29N3O2
3,6-diethyl-N-(1-ethylpropyl)-5-(2-hydroxy-4-methoxyphenyl)pyrazin-2-amine
—— 1,5-Bis-(4-hydroxy-phenyl)-pentan 10365-62-5 C17H20O2
1,5-Bis-(4-hydroxy-phenyl)-pentan
—— OXY-Isoprenaline 53562-78-0 C12H19NO4
OXY-Isoprenaline
—— 1-[3-(furan-2-yl)-4,5-dihydro-5-(3-hydroxyphenyl)pyrazol-1-yl]ethanone 685132-35-8 C15H14N2O3
1-[3-(furan-2-yl)-4,5-dihydro-5-(3-hydroxyphenyl)pyrazol-1-yl]ethanone
—— 3,3'-(selenine-2,5-diyl)diphenol 1078733-92-2 C16H12O2Se
3,3'-(selenine-2,5-diyl)diphenol
—— 2-bromosyringaldehyde 137214-61-0 C9H9BrO4
2-bromosyringaldehyde
—— 6-(3,4-dihydroxy-phenyl)-hexanoic acid 95301-42-1 C12H16O4
6-(3,4-dihydroxy-phenyl)-hexanoic acid
—— ethyl 2-(3,5-dihydroxyphenyl)acetate 66761-55-5 C10H12O4
ethyl 2-(3,5-dihydroxyphenyl)acetate
—— 3,5-Dibrom-4-aethyl-phenol 115281-01-1 C8H8Br2O
3,5-Dibrom-4-aethyl-phenol
—— 2,6-Bis-(hydroxymethyl)-hemellitenol 103564-88-1 C11H16O3
2,6-Bis-(hydroxymethyl)-hemellitenol
—— calicheamicin pseudoaglycon 108212-77-7 C40H47IN2O15S4
calicheamicin pseudoaglycon
—— 2-hexadecyl-hydroquinone 4595-26-0 C22H38O2
2-hexadecyl-hydroquinone
—— 3-(5,5-dimethyl-[1,3]dioxolan-2-yl)phenol 863408-22-4 C12H16O3
3-(5,5-dimethyl-[1,3]dioxolan-2-yl)phenol
—— 2-n-Hexadecyl-4-methoxy-phenol 148666-00-6 C23H40O2
2-n-Hexadecyl-4-methoxy-phenol
—— N-Chloracetyl-3,5-dihydroxy-benzylamin 53389-74-5 C9H10ClNO3
N-Chloracetyl-3,5-dihydroxy-benzylamin
—— 4-methoxy-2,5-dimethyl-phenethyl alcohol 858855-72-8 C11H16O2
4-methoxy-2,5-dimethyl-phenethyl alcohol
—— (2,5-dihydroxy-phenyl)-[1,4]benzoquinone 3286-05-3 C12H8O4
(2,5-dihydroxy-phenyl)-[1,4]benzoquinone
—— N-benzyl-β-(3-hydroxy-4-methoxyphenyl)ethylamine 1523248-30-7 C16H19NO2
N-benzyl-β-(3-hydroxy-4-methoxyphenyl)ethylamine
—— 5-azido-2-methoxyphenol 876012-81-6 C7H7N3O2
5-azido-2-methoxyphenol
—— 5-(cyclopropyl(4-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 1073545-86-4 C16H18O5
5-(cyclopropyl(4-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
—— N-(3-hydroxy-4-methoxyphenethyl)-2-phenylacetamide 118822-54-1 C17H19NO3
N-(3-hydroxy-4-methoxyphenethyl)-2-phenylacetamide
—— 4-(2-(bis(2-pyridylmethyl)amino)ethylaminomethyl)1,2-benzenediol 851510-32-2 C21H24N4O2
4-(2-(bis(2-pyridylmethyl)amino)ethylaminomethyl)1,2-benzenediol
—— 4-[(4-Methylphenyl)iminomethyl]benzene-1,2-diol 304456-11-9 C14H13NO2
4-[(4-Methylphenyl)iminomethyl]benzene-1,2-diol
—— 2-(3-hydroxy-4-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide 1395084-64-6 C18H21NO4
2-(3-hydroxy-4-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
—— 4-(4-Hydroxyphenoxy)butanal 1005008-17-2 C10H12O3
4-(4-Hydroxyphenoxy)butanal
—— 2-methoxy-5-{2-[2-(4-methoxyphenyl)ethylamino]ethyl}phenol 1395084-71-5 C18H23NO3
2-methoxy-5-{2-[2-(4-methoxyphenyl)ethylamino]ethyl}phenol
—— (S)-N-Boc-isoproterenol 1044185-59-2 C16H25NO5
(S)-N-Boc-isoproterenol
—— 3,4,5,6,7,8-Hexahydro-6-((4-hydroxyphenyl)methyl)-3-methylquinolin-2[1H]-one 171492-86-7 C17H21NO2
3,4,5,6,7,8-Hexahydro-6-((4-hydroxyphenyl)methyl)-3-methylquinolin-2[1H]-one
—— 4-allyl-2-cyclopentylphenol 122030-11-9 C14H18O
4-allyl-2-cyclopentylphenol
—— 7-bromo-1-(4-hydroxyphenyl)heptane 1004304-60-2 C13H19BrO
7-bromo-1-(4-hydroxyphenyl)heptane
—— 2,6-Dimethyl-4-(2-thiophen-3-yl-vinyl)-phenol 127035-90-9 C14H14OS
2,6-Dimethyl-4-(2-thiophen-3-yl-vinyl)-phenol
—— 5-(2,4-dihydroxy-phenyl)-valeric acid methyl ester 159952-76-8 C12H16O4
5-(2,4-dihydroxy-phenyl)-valeric acid methyl ester
—— Methyl 5-(3-chloro-2,4-dihydroxyphenyl)pentanoate 851226-35-2 C12H15ClO4
Methyl 5-(3-chloro-2,4-dihydroxyphenyl)pentanoate
—— 5-(4-hydroxy-3-methoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 153562-26-6 C14H16O6
5-(4-hydroxy-3-methoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
—— 4-(7-Pentadecyl-2,3-dihydro-1,4-benzoxathiin-2-yl)benzene-1,2-diol 1282616-24-3 C29H42O3S
4-(7-Pentadecyl-2,3-dihydro-1,4-benzoxathiin-2-yl)benzene-1,2-diol
—— 4-(7-Hydroxy-5-pentadecyl-2,3-dihydro-1,4-benzoxathiin-2-yl)benzene-1,2-diol 1282616-26-5 C29H42O4S
4-(7-Hydroxy-5-pentadecyl-2,3-dihydro-1,4-benzoxathiin-2-yl)benzene-1,2-diol
—— 4-(7-Hydroxy-8-methyl-5-pentadecyl-2,3-dihydro-1,4-benzoxathiin-2-yl)benzene-1,2-diol 1282616-29-8 C30H44O4S
4-(7-Hydroxy-8-methyl-5-pentadecyl-2,3-dihydro-1,4-benzoxathiin-2-yl)benzene-1,2-diol
—— (E)-4-[2-((3-phenylprop-1-yl)sulfonyl)vinyl]benzene-1,2-diol 1609007-93-3 C17H18O4S
(E)-4-[2-((3-phenylprop-1-yl)sulfonyl)vinyl]benzene-1,2-diol
—— (E)-4-[2-((3-phenylprop-1-yl)sulfinyl)vinyl]benzene-1,2-diol 1609008-01-6 C17H18O3S
(E)-4-[2-((3-phenylprop-1-yl)sulfinyl)vinyl]benzene-1,2-diol
—— (E)-3-(4-hydroxy-3-nitrophenyl)acrylonitrile 654674-80-3 C9H6N2O3
(E)-3-(4-hydroxy-3-nitrophenyl)acrylonitrile
—— (E)-3-(2-hydroxy-3-nitrophenyl)prop-2-enenitrile 625850-65-9 C9H6N2O3
(E)-3-(2-hydroxy-3-nitrophenyl)prop-2-enenitrile
—— 4-hydroxy-3-methoxy-5-(trifluoromethyl)benzaldehyde 116314-60-4 C9H7F3O3
4-hydroxy-3-methoxy-5-(trifluoromethyl)benzaldehyde
—— (E)-2-hydroxy-4,6-dimethoxystyryl-4-methoxybenzylsulfone 334969-45-8 C18H20O6S
(E)-2-hydroxy-4,6-dimethoxystyryl-4-methoxybenzylsulfone
—— NSC48443 6641-18-5 C20H32N2O2
NSC48443
—— (E)-4-[2-(((4-methoxyphenyl)methyl)sulfonyl)vinyl]-benzene-1,2-diol 1609007-98-8 C16H16O5S
(E)-4-[2-(((4-methoxyphenyl)methyl)sulfonyl)vinyl]-benzene-1,2-diol