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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
—— 5-[1-[(1Z)-1-hexenyl]cyclopentyl]resorcinol 941583-80-8 C17H24O2
5-[1-[(1Z)-1-hexenyl]cyclopentyl]resorcinol
—— 2-(3,5-dihydroxyphenyl)-2-hexyl-1,3-dithiolane 205746-53-8 C15H22O2S2
2-(3,5-dihydroxyphenyl)-2-hexyl-1,3-dithiolane
—— 5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol 330855-39-5 C13H18O2S2
5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol
—— 2-Hydroxy-4,6-dimethoxybenzonitrile 115661-21-7 C9H9NO3
2-Hydroxy-4,6-dimethoxybenzonitrile
—— 3-(3,5-dihydroxyphenyl)-1-propanol 93359-28-5 C9H12O3
3-(3,5-dihydroxyphenyl)-1-propanol
—— N-(2-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide 677320-92-2 C19H18ClN3O4
N-(2-chlorophenyl)-4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 5-(3,5-dihydroxyphenyl)pentanoic acid 74356-41-5 C11H14O4
5-(3,5-dihydroxyphenyl)pentanoic acid
—— methyl 3-(3'.5'-dihydroxyphenyl)propanoate 64794-00-9 C10H12O4
methyl 3-(3'.5'-dihydroxyphenyl)propanoate
—— 1,3-dihydroxy-5-<14'-(3'',5''-dihydroxyphenyl)-cis-6'-tetradecenyl>benzene 52483-24-6 C26H36O4
1,3-dihydroxy-5-<14'-(3'',5''-dihydroxyphenyl)-cis-6'-tetradecenyl>benzene
—— 4-[(Octan-2-yl)sulfanyl]benzene-1,2-diol 111040-79-0 C14H22O2S
4-[(Octan-2-yl)sulfanyl]benzene-1,2-diol
—— 4-hydroxybenzaldehyde amidinohydrazone 4719-73-7 C8H10N4O
4-hydroxybenzaldehyde amidinohydrazone
—— Salicylidenamino-guanidin 67763-12-6 C8H10N4O
Salicylidenamino-guanidin
—— 4-[(diphenylphosphanyl)methyl]benzene-1,2-diol 922721-40-2 C19H17O2P
4-[(diphenylphosphanyl)methyl]benzene-1,2-diol
—— 4-Nitroso-5-methylresorcinol 116480-13-8 C7H7NO3
4-Nitroso-5-methylresorcinol
—— 2-thiopyrogallol 2103-60-8 C6H6O2S
2-thiopyrogallol
—— 4-[2-(Benzenesulfonyl)ethyl]-5-chlorobenzene-1,2-diol 126644-87-9 C14H13ClO4S
4-[2-(Benzenesulfonyl)ethyl]-5-chlorobenzene-1,2-diol
—— 6-(4-hydroxy-2-methylphenyl)-5-methylpyrazin-2-ol 1609581-89-6 C12H12N2O2
6-(4-hydroxy-2-methylphenyl)-5-methylpyrazin-2-ol
—— 2-Bromo-4-nitro-6-(trifluoromethyl)phenol 105653-11-0 C7H3BrF3NO3
2-Bromo-4-nitro-6-(trifluoromethyl)phenol
—— 6-(4-hydroxy-2-methylphenyl)-1,5-dimethylpyrazin-2(1H)-one 1609259-39-3 C13H14N2O2
6-(4-hydroxy-2-methylphenyl)-1,5-dimethylpyrazin-2(1H)-one
—— 4-bromo-5-chloropyrocatechol 369354-51-8 C6H4BrClO2
4-bromo-5-chloropyrocatechol
—— 4-[8-(4-Tritylphenoxy)octoxy]phenol 407634-82-6 C39H40O3
4-[8-(4-Tritylphenoxy)octoxy]phenol
—— 2-methyl-4-chloro-5-ethylaminophenol 110102-87-9 C9H12ClNO
2-methyl-4-chloro-5-ethylaminophenol
—— 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-methoxy-4-pentafluoroethyl-6(1H)-pyrimidinone 115784-68-4 C13H7ClF6N2O3
1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-methoxy-4-pentafluoroethyl-6(1H)-pyrimidinone
—— N'-(2-hydroxy-5-methylphenyl)-N,N-bis(prop-2-en-1-yl)methanimidamide 1323158-81-1 C14H18N2O
N'-(2-hydroxy-5-methylphenyl)-N,N-bis(prop-2-en-1-yl)methanimidamide
—— 4-methyl-2-(pyrrolidin-1-ylmethyleneamino)phenol 1323158-60-6 C12H16N2O
4-methyl-2-(pyrrolidin-1-ylmethyleneamino)phenol
—— 3-allylresorcinol 142039-78-9 C9H10O2
3-allylresorcinol
—— Phenol, 4-[[(phenylmethyl)thio]methyl]- 54373-22-7 C14H14OS
Phenol, 4-[[(phenylmethyl)thio]methyl]-
—— 3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methyl-1,3,4,5-tetrahydropyrrolo<4,3,2-de>isoquinoline 111168-77-5 C19H20N2O3
3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methyl-1,3,4,5-tetrahydropyrrolo<4,3,2-de>isoquinoline
—— 5-methyl-4-nitro-2-(2-propenyl)phenol 140427-28-7 C10H11NO3
5-methyl-4-nitro-2-(2-propenyl)phenol
—— 2-Chlor-3-methyl-4-nitrophenol 88062-27-5 C7H6ClNO3
2-Chlor-3-methyl-4-nitrophenol
—— 2,6-bis(diethylaminomethyl)-3-methyl-4-nitrophenol 133394-06-6 C17H29N3O3
2,6-bis(diethylaminomethyl)-3-methyl-4-nitrophenol
—— 2-methyl-5-morpholin-4-ylmethyl-benzene-1,4-diol 30483-05-7 C12H17NO3
2-methyl-5-morpholin-4-ylmethyl-benzene-1,4-diol
—— 3-(benzo[d][1,3]dioxol-5-yl)-1-(cis-3,5-dimethylpiperazin-1-yl)-3-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-one 1415387-85-7 C24H30N2O6
3-(benzo[d][1,3]dioxol-5-yl)-1-(cis-3,5-dimethylpiperazin-1-yl)-3-(2-hydroxy-4,6-dimethoxyphenyl)propan-1-one
—— 2,5-dihydroxybenzyl mercaptan 5273-75-6 C7H8O2S
2,5-dihydroxybenzyl mercaptan
—— 2,5-dihydroxy-4-methyl-benzyl alcohol 939019-26-8 C8H10O3
2,5-dihydroxy-4-methyl-benzyl alcohol
—— tert-butyl-diphenylsilyl 4-hydroxy-3-methylphenyl ether 108534-49-2 C23H26O2Si
tert-butyl-diphenylsilyl 4-hydroxy-3-methylphenyl ether
—— p-benzoquinone/methylhydroquinone 1:1 complex 55836-33-4 C6H4O2*C7H8O2
p-benzoquinone/methylhydroquinone 1:1 complex
—— 4-[6-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]hexoxy]phenol 702701-66-4 C25H44O9
4-[6-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]hexoxy]phenol
—— 4-((tert-butyldimethylsilyl)oxy)-2-methylphenol 440676-95-9 C13H22O2Si
4-((tert-butyldimethylsilyl)oxy)-2-methylphenol
—— 3-methyl-4-((tetrahydro-2H-pyran-2-yl)oxy)phenol 854907-84-9 C12H16O3
3-methyl-4-((tetrahydro-2H-pyran-2-yl)oxy)phenol
—— methyl-[1,4]benzoquinone; compound with 2-methyl-hydroquinone 87970-31-8 C7H6O2*C7H8O2
methyl-[1,4]benzoquinone; compound with 2-methyl-hydroquinone
—— 2-[(4-Hydroxyphenyl)(diphenyl)methyl]phenol 113714-12-8 C25H20O2
2-[(4-Hydroxyphenyl)(diphenyl)methyl]phenol
—— 2-methyl-but-(2E)-2-enoic acid [(2,5-dihydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-4-methoxy-phenyl]amide 622347-59-5 C20H31NO5
2-methyl-but-(2E)-2-enoic acid [(2,5-dihydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-4-methoxy-phenyl]amide
—— 2-(2',5'-dihydroxy-4'-methoxyphenyl)-5-methoxy-p-benzoquinone 51281-73-3 C14H12O6
2-(2',5'-dihydroxy-4'-methoxyphenyl)-5-methoxy-p-benzoquinone
—— 2,3,5-tribromo-6-methoxybenzene-1,4-diol 786691-20-1 C7H5Br3O3
2,3,5-tribromo-6-methoxybenzene-1,4-diol
—— sodium 3-methyl-4-nitrophenolate 2666-76-4 C7H6NO3*Na
sodium 3-methyl-4-nitrophenolate
—— 2,5-dihydroxy-3-methoxybenzaldehyde 2179-22-8 C8H8O4
2,5-dihydroxy-3-methoxybenzaldehyde
—— 3-methoxy-4-(triisopropylsiloxy)phenol 218903-27-6 C16H28O3Si
3-methoxy-4-(triisopropylsiloxy)phenol
—— 5-Hydroxy-N,N'-(6-methylpyridin-2-yl)benzene-1,3-dicarbonamide 335661-43-3 C20H18N4O3
5-Hydroxy-N,N'-(6-methylpyridin-2-yl)benzene-1,3-dicarbonamide
—— 2-(4-methoxyphenyl)ethyl 4-nitrophenylcarbonate 485798-68-3 C16H15NO6
2-(4-methoxyphenyl)ethyl 4-nitrophenylcarbonate