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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
—— 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
—— 4-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone 923267-63-4 C11H10O4S
4-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone
—— 3-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone 923267-62-3 C11H10O4S
3-[(2-furylmethyl)sulfanyl]hydroxyhydroquinone
—— 3,4-bis[(2-furylmethyl)sulfanyl]hydroxyhydroquinone 923267-64-5 C16H14O5S2
3,4-bis[(2-furylmethyl)sulfanyl]hydroxyhydroquinone
—— 4-(nonyloxy)benzene-1,2-diol 263159-84-8 C15H24O3
4-(nonyloxy)benzene-1,2-diol
—— 4-(octyloxy)benzene-1,2-diol 59263-61-5 C14H22O3
4-(octyloxy)benzene-1,2-diol
—— 2,4-dimethoxyethoxymethyloxyphenol 312608-04-1 C14H22O7
2,4-dimethoxyethoxymethyloxyphenol
—— 3-chloro-4-(4-methoxybenzyloxy)phenethyl methanesulfonate 1147391-92-1 C17H19ClO5S
3-chloro-4-(4-methoxybenzyloxy)phenethyl methanesulfonate
—— 2-methoxy-6-methyl-4-[2-(thien-2-yl)ethenyl]phenol 127035-66-9 C14H14O2S
2-methoxy-6-methyl-4-[2-(thien-2-yl)ethenyl]phenol
—— 2-Brom-4-nitroso-phenol 15516-58-2 C6H4BrNO2
2-Brom-4-nitroso-phenol
—— 2,6-dimethoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol 127035-72-7 C14H14O3S
2,6-dimethoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 2-Ethyl-6-methoxy-4-(2-thiophen-2-yl-vinyl)-phenol 127035-67-0 C15H16O2S
2-Ethyl-6-methoxy-4-(2-thiophen-2-yl-vinyl)-phenol
—— 2,6-dimethyl-4-[2-(2-thienyl)ethyl]phenol 127035-96-5 C14H16OS
2,6-dimethyl-4-[2-(2-thienyl)ethyl]phenol
—— 4-[(2S,3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-3,4-dihydro-2H-pyran-6-yl]-2-bromophenol 143144-64-3 C24H41BrO4Si2
4-[(2S,3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-3,4-dihydro-2H-pyran-6-yl]-2-bromophenol
—— 2-chloro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol 127063-62-1 C13H11ClOS
2-chloro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 2-fluoro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol 127035-69-2 C13H11FOS
2-fluoro-6-methyl-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 2-fluoro-6-methoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol 127035-71-6 C13H11FO2S
2-fluoro-6-methoxy-4-[(E)-2-thiophen-2-ylethenyl]phenol
—— 4-hydroxy-2-methoxyphenylacetic acid 883988-36-1 C9H10O4
4-hydroxy-2-methoxyphenylacetic acid
—— 2-bromo-4-(3,4-dihydro-2H-pyran-6-yl)phenol 143144-61-0 C11H11BrO2
2-bromo-4-(3,4-dihydro-2H-pyran-6-yl)phenol
—— 3-Ethyl-5-methoxy-4-hydroxybenzaldehyde 125722-35-2 C10H12O3
3-Ethyl-5-methoxy-4-hydroxybenzaldehyde
—— 2-Allyl-6-methyl-4-(2-thiophen-2-yl-vinyl)-phenol 127035-70-5 C16H16OS
2-Allyl-6-methyl-4-(2-thiophen-2-yl-vinyl)-phenol