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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
—— [(R)-1-(4-hydroxy-phenyl)-2-(4-methyl-piperazin-1-yl)ethyl]carbamic acid tert-butyl ester 1286280-64-5 C18H29N3O3
[(R)-1-(4-hydroxy-phenyl)-2-(4-methyl-piperazin-1-yl)ethyl]carbamic acid tert-butyl ester
—— 1-(3-Bromo-4-hydroxy-benzyl)-1,3-dihydro-imidazole-2-thione 95333-48-5 C10H9BrN2OS
1-(3-Bromo-4-hydroxy-benzyl)-1,3-dihydro-imidazole-2-thione
—— 2,4-bis(pyridin-4-ylmethyl)benzene-1,3,5-triol 1233132-27-8 C18H16N2O3
2,4-bis(pyridin-4-ylmethyl)benzene-1,3,5-triol
—— 6-chloro-3-methyl-2-(prop-2-en-1-yl)phenol 1154740-69-8 C10H11ClO
6-chloro-3-methyl-2-(prop-2-en-1-yl)phenol
—— (E)-6-chloro-3-methyl-2-(prop-1-enyl)phenol 1310800-52-2 C10H11ClO
(E)-6-chloro-3-methyl-2-(prop-1-enyl)phenol
—— 1-(3-hydroxyphenyl)guanidine hydrochloride 24067-09-2 C7H9N3O*ClH
1-(3-hydroxyphenyl)guanidine hydrochloride
—— 4,5-dimethoxy-2-propylphenol 6906-69-0 C11H16O3
4,5-dimethoxy-2-propylphenol
—— 3-(ethylamino)-2-methylphenol 1310581-20-4 C9H13NO
3-(ethylamino)-2-methylphenol
—— 4,5-dimethoxy-2-hydroxybenzonitrile 115661-20-6 C9H9NO3
4,5-dimethoxy-2-hydroxybenzonitrile
—— 4-Hydroxy-3'-oxodecylbenzene 139446-84-7 C16H24O2
4-Hydroxy-3'-oxodecylbenzene
—— 4,5-dimethoxy-2-(1-methylallyl)phenol 118326-04-8 C12H16O3
4,5-dimethoxy-2-(1-methylallyl)phenol
—— 2-hydroxy-3-iodo-5,6-dimethoxybenzaldehyde 1361394-00-4 C9H9IO4
2-hydroxy-3-iodo-5,6-dimethoxybenzaldehyde
—— 2-hydroxy-4,5-dimethoxyphenylboronic acid 681431-19-6 C8H11BO5
2-hydroxy-4,5-dimethoxyphenylboronic acid
—— 3,4-dimethoxy-6-(2'-hydroxy)ethylphenol 70874-61-2 C10H14O4
3,4-dimethoxy-6-(2'-hydroxy)ethylphenol
—— 2,6-dimethyl-4-[(E)-2-(5-methylthiophen-2-yl)ethenyl]phenol 127035-89-6 C15H16OS
2,6-dimethyl-4-[(E)-2-(5-methylthiophen-2-yl)ethenyl]phenol
—— 3-Hydroxy-2-methoxy-N-methylbenzamide 1190090-16-4 C9H11NO3
3-Hydroxy-2-methoxy-N-methylbenzamide
—— 2-(2'-hydroxy-4',5'-dimethoxyphenyl)-5-methoxy-[1,4]benzoquinone 85969-39-7 C15H14O6
2-(2'-hydroxy-4',5'-dimethoxyphenyl)-5-methoxy-[1,4]benzoquinone
—— 4-hydroxy-2-methoxy-N-methyl-benzamide 1190090-24-4 C9H11NO3
4-hydroxy-2-methoxy-N-methyl-benzamide
—— 2-[[(1R,4aR,8aR)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-1-yl]methyl]-3,4-dimethoxyphenol 180912-49-6 C20H30O3
2-[[(1R,4aR,8aR)-8a-methyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-1-yl]methyl]-3,4-dimethoxyphenol
—— 4-(thiazol-5-yl)phenol 342616-98-2 C9H7NOS
4-(thiazol-5-yl)phenol
—— 3-(thiazol-5-yl)phenol 68535-59-1 C9H7NOS
3-(thiazol-5-yl)phenol
—— 2-tert-butyl-4,5-dimethoxy-phenol 855401-21-7 C12H18O3
2-tert-butyl-4,5-dimethoxy-phenol
—— N-(2-benzamidoethyl)-2-hydroxy-5-nitrobenzamide 1533427-34-7 C16H15N3O5
N-(2-benzamidoethyl)-2-hydroxy-5-nitrobenzamide
—— 2-chloro-4,5-dimethoxyphenol 18093-03-3 C8H9ClO3
2-chloro-4,5-dimethoxyphenol
—— N-(2-aminoethyl)-2-hydroxy-5-nitrobenzamide 1196131-89-1 C9H11N3O4
N-(2-aminoethyl)-2-hydroxy-5-nitrobenzamide
—— 4,5-diamino-pyrocatechol 159661-41-3 C6H8N2O2
4,5-diamino-pyrocatechol
—— 2,3,4-trihydroxy-6-pentyl-benzaldehyde 860240-80-8 C12H16O4
2,3,4-trihydroxy-6-pentyl-benzaldehyde
—— N-hydroxy-3,5-bis-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide 1208112-51-9 C16H16N4O3
N-hydroxy-3,5-bis-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide
—— 3-nitro-5-[2-(pyridin-3-yl)-4-thiazolyl]pyrocatechol 134611-29-3 C14H9N3O4S
3-nitro-5-[2-(pyridin-3-yl)-4-thiazolyl]pyrocatechol
—— (5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]propyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-1,3-thiazol-4(5H)-one 1415582-55-6 C28H27N7O4S2
(5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]propyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-1,3-thiazol-4(5H)-one
—— 2-(piperidin-1-ylimino-methyl)-phenol 59244-22-3 C12H16N2O
2-(piperidin-1-ylimino-methyl)-phenol
—— 1-(5'-hydroxy-2'-nitrophenyl)-2-propen-1-ol 187793-42-6 C9H9NO4
1-(5'-hydroxy-2'-nitrophenyl)-2-propen-1-ol
—— 1-{[(1S,4aS,8aS)-decahydro-2-methylene-5,5,8a-trimethylnaphthalen-1-yl]methyl}-2,6-dihydroxy-4-(hydroxymethyl)benzene 1204405-06-0 C22H32O3
1-{[(1S,4aS,8aS)-decahydro-2-methylene-5,5,8a-trimethylnaphthalen-1-yl]methyl}-2,6-dihydroxy-4-(hydroxymethyl)benzene
—— 6-(1-(N-(2,2-dimethoxyethyl)amino)-2-(benzyloxy)ethyl)-2-metoxyphenol 147624-60-0 C15H25NO5
6-(1-(N-(2,2-dimethoxyethyl)amino)-2-(benzyloxy)ethyl)-2-metoxyphenol
—— 4-methoxy-3-hydroxy benzylamino acetaldehyde diethylacetal 1810-57-7 C14H23NO4
4-methoxy-3-hydroxy benzylamino acetaldehyde diethylacetal
—— 3-methoxy-4-hydroxy benzylamino acetaldehyde diethylacetal 862845-47-4 C14H23NO4
3-methoxy-4-hydroxy benzylamino acetaldehyde diethylacetal
—— 2,4,6-trinitro-3-trifluoromethyl-phenol 384-77-0 C7H2F3N3O7
2,4,6-trinitro-3-trifluoromethyl-phenol
—— (<i>S</i>)-2-bromo-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid 90484-41-6 C9H7BrN2O7
(<i>S</i>)-2-bromo-3-(4-hydroxy-3,5-dinitro-phenyl)-propionic acid
—— 4-(4-Dimethylamino-anilino)-3-methoxy-phenol 57524-54-6 C15H18N2O2
4-(4-Dimethylamino-anilino)-3-methoxy-phenol
—— ethyl 3-(3,5-dibromo-4-hydroxyphenyl)propionate 117896-41-0 C11H12Br2O3
ethyl 3-(3,5-dibromo-4-hydroxyphenyl)propionate
—— [carboxymethyl-(2-hydroxy-5-nitro-benzyl)-amino]-acetic acid hydrochloride 882006-30-6 C11H13N2O7*Cl
[carboxymethyl-(2-hydroxy-5-nitro-benzyl)-amino]-acetic acid hydrochloride
—— 4-bromo-2,3,5-trimethyl-6-nitrophenol 1277193-09-5 C9H10BrNO3
4-bromo-2,3,5-trimethyl-6-nitrophenol
—— 1-n-Octyl-2-(2-hydroxy-5-nitrophenyl)-Δ<sup>2</sup>-imidazolin 84354-91-6 C17H25N3O3
1-n-Octyl-2-(2-hydroxy-5-nitrophenyl)-Δ<sup>2</sup>-imidazolin
—— N-n-Octyl-N'-(2-hydroxy-3-nitrobenzoyl)-diaminoethan-1,2 86840-91-7 C17H27N3O4
N-n-Octyl-N'-(2-hydroxy-3-nitrobenzoyl)-diaminoethan-1,2
—— 1-n-Octyl-2-(2-hydroxy-3-nitrophenyl)-Δ<sup>2</sup>-imidazolin 86840-84-8 C17H25N3O3
1-n-Octyl-2-(2-hydroxy-3-nitrophenyl)-Δ<sup>2</sup>-imidazolin
—— 5-cyclopentylbenzene-1,3-diol 2931-30-8 C11H14O2
5-cyclopentylbenzene-1,3-diol
—— 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylic acid 712347-85-8 C10H9NO4
4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylic acid
—— N-salicylhydroxylamine hydrochloride 1394382-14-9 C7H9NO2*ClH
N-salicylhydroxylamine hydrochloride
—— (R)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol 134582-18-6 C12H17ClO3
(R)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol
—— 3,3'-dibromo-5,5',α,α'-tetramethyl-bis(salicylaldehyde)ethylenediamine 906433-44-1 C20H22Br2N2O2
3,3'-dibromo-5,5',α,α'-tetramethyl-bis(salicylaldehyde)ethylenediamine