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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
—— (E)-1-[2-hydroxy-4-methoxy-5-(morpholin-4-ylmethyl)phenyl]-3-pyridin-3-ylprop-2-en-1-one 1064288-07-8 C20H22N2O4
(E)-1-[2-hydroxy-4-methoxy-5-(morpholin-4-ylmethyl)phenyl]-3-pyridin-3-ylprop-2-en-1-one
—— 6-Allyl-3-bromo-4-[1,3]dioxolan-2-yl-2-methoxy-phenol 1027270-48-9 C13H15BrO4
6-Allyl-3-bromo-4-[1,3]dioxolan-2-yl-2-methoxy-phenol
—— 2,6-Bis-(1-methylnonyl)-phenol 82971-18-4 C26H46O
2,6-Bis-(1-methylnonyl)-phenol
—— 2-Cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethyl pivalate 154699-01-1 C17H22O3
2-Cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethyl pivalate
—— 3-<(2,5-Dihydroxyphenyl)amino>-5,5-dimethyl-2-cyclohexen-1-on 117527-09-0 C14H17NO3
3-<(2,5-Dihydroxyphenyl)amino>-5,5-dimethyl-2-cyclohexen-1-on
—— 2-Cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethanol 154699-00-0 C12H14O2
2-Cyclopropylidene-2-(2-hydroxy-4-methylphenyl)ethanol
—— 4-hydroxyphenyl 3-phenylselenylprop-2-yn-1-yl ether 1147711-59-8 C15H12O2Se
4-hydroxyphenyl 3-phenylselenylprop-2-yn-1-yl ether
—— 2-(4,6-diethyl-2-hydrazino-pyrimidin-5-yl)-phenol 53511-48-1 C14H18N4O
2-(4,6-diethyl-2-hydrazino-pyrimidin-5-yl)-phenol
—— 4-butyl-1-(3-hydroxy-phenyl)-2-phenyl-pyrazolidine-3,5-dione 98196-00-0 C19H20N2O3
4-butyl-1-(3-hydroxy-phenyl)-2-phenyl-pyrazolidine-3,5-dione
—— 1,2-Bis-m-hydroxyphenyl-4-n-butyl-pyrazolidin-3,5-dion 1242-28-0 C19H20N2O4
1,2-Bis-m-hydroxyphenyl-4-n-butyl-pyrazolidin-3,5-dion
—— 2-(Di-morpholin-4-yl-methyl)-6-nitro-phenol 183364-35-4 C15H21N3O5
2-(Di-morpholin-4-yl-methyl)-6-nitro-phenol
—— difluoromethyl-phenol 271249-71-9 C7H6F2O
difluoromethyl-phenol
—— 2-(5,7-diethyl-tetrazolo[1,5-<i>a</i>]pyrimidin-6-yl)-phenol 53511-54-9 C14H15N5O
2-(5,7-diethyl-tetrazolo[1,5-<i>a</i>]pyrimidin-6-yl)-phenol
—— 4-(2-Amino-1-hydroxy-ethyl)-2-fluoro-phenol; hydrochloride 37302-03-7 C8H10FNO2*ClH
4-(2-Amino-1-hydroxy-ethyl)-2-fluoro-phenol; hydrochloride
—— (S)-3-(5-methyl-4,5-dihydrooxazol-2-yl)phenol 1188498-91-0 C10H11NO2
(S)-3-(5-methyl-4,5-dihydrooxazol-2-yl)phenol
—— 2-{(E)-[(4-methylphenyl)imino]methyl}-4-nitrophenol 20772-75-2 C14H12N2O3
2-{(E)-[(4-methylphenyl)imino]methyl}-4-nitrophenol
—— (+/-)-2,6-Dimethyl-4-<3-hydroxy-4-<(trimethylsilyl)methyl>-4-pentenyl>phenol 118631-04-2 C17H28O2Si
(+/-)-2,6-Dimethyl-4-<3-hydroxy-4-<(trimethylsilyl)methyl>-4-pentenyl>phenol
—— diethyl N-(3-chloro-2-hydroxyphenyl)aminomethylenemalonate 121996-73-4 C14H16ClNO5
diethyl N-(3-chloro-2-hydroxyphenyl)aminomethylenemalonate
—— 4-[2-(Chloromethyl)-1,3-dioxolan-2-yl]phenol 20535-60-8 C10H11ClO3
4-[2-(Chloromethyl)-1,3-dioxolan-2-yl]phenol
—— 2-(1-Butylheptyl)-phenol 17404-53-4 C17H28O
2-(1-Butylheptyl)-phenol
—— 2-(1-Butylpentyl)-phenol 17404-48-7 C15H24O
2-(1-Butylpentyl)-phenol
—— o-(1-butyl-2,2-difluorovinyl)phenol 195734-35-1 C12H14F2O
o-(1-butyl-2,2-difluorovinyl)phenol
—— gallic acid laurylamide 99504-48-0 C19H31NO4
gallic acid laurylamide
—— 2-(3-Hydroxyphenyl)-6,6-dimethylcyclohex-2-ene-1,4-dione 1222850-82-9 C14H14O3
2-(3-Hydroxyphenyl)-6,6-dimethylcyclohex-2-ene-1,4-dione
—— 2,5-dimethyl-trans-2,5-di(3,5-dinitro-4-hydroxyphenyl)pyrrolidin-1-oxyl 124190-07-4 C18H16N5O11
2,5-dimethyl-trans-2,5-di(3,5-dinitro-4-hydroxyphenyl)pyrrolidin-1-oxyl
—— Picric acid; compound with [3-(benzooxazol-2-yloxy)-propyl]-dimethyl-amine 89114-22-7 C6H3N3O7*C12H16N2O2
Picric acid; compound with [3-(benzooxazol-2-yloxy)-propyl]-dimethyl-amine
—— 4-Nitro-2-<3-nitro-benzylidenamino>-phenol 90284-73-4 C13H9N3O5
4-Nitro-2-<3-nitro-benzylidenamino>-phenol
—— Butyl-carbamic acid 4-[2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethylamino]-pentyl ester 88719-67-9 C18H30N2O5
Butyl-carbamic acid 4-[2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethylamino]-pentyl ester
—— 3,3'-thiene-2,5-diyldiphenol 1078733-86-4 C16H12O2S
3,3'-thiene-2,5-diyldiphenol
—— 4-methoxy-3-(methoxymethyl)phenol 59907-65-2 C9H12O3
4-methoxy-3-(methoxymethyl)phenol
—— 5-(2-anilino-4-thiazolyl)-3-nitropyrocatechol 134612-69-4 C15H11N3O4S
5-(2-anilino-4-thiazolyl)-3-nitropyrocatechol
—— 4-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-2-chloro-6-trimethylsilylphenol 1127943-59-2 C27H35ClO2Si2
4-[2-[Tert-butyl(diphenyl)silyl]oxyethyl]-2-chloro-6-trimethylsilylphenol
—— N,N'-hexamethylene-bis-(2,5-dihydroxyacetophenone) 61909-97-5 C22H28N2O4
N,N'-hexamethylene-bis-(2,5-dihydroxyacetophenone)
—— (2E,4E)-5-(3,4-dimethoxyphenyl)-1-(2-hydroxy-6-methoxyphenyl)penta-2,4-dien-1-one 1422364-12-2 C20H20O5
(2E,4E)-5-(3,4-dimethoxyphenyl)-1-(2-hydroxy-6-methoxyphenyl)penta-2,4-dien-1-one
—— 1-carbamimidoyl-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]urea;2,4,6-trinitrophenol —— C13H17N7O12
1-carbamimidoyl-3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]urea;2,4,6-trinitrophenol
—— (2E,4E)-1-(2-hydroxy-6-methoxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)penta-2,4-dien-1-one 1422364-14-4 C19H18O5
(2E,4E)-1-(2-hydroxy-6-methoxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)penta-2,4-dien-1-one
—— (2Z,4E)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxy-6-methoxyphenyl)penta-2,4-dien-1-one 1422364-17-7 C19H18O6
(2Z,4E)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxy-6-methoxyphenyl)penta-2,4-dien-1-one
—— 5-(2-hydroxy-4-methyphenyl)-3-phenylisoxazole 140885-84-3 C16H13NO2
5-(2-hydroxy-4-methyphenyl)-3-phenylisoxazole
—— 6-Methoxyquinoline; 2,4,6-trinitrophenol 7533-21-3 C16H12N4O8
6-Methoxyquinoline; 2,4,6-trinitrophenol
—— 3-((tert-butyldiphenylsilyl)oxy)-4-methoxy-5-((trimethylsilyl)ethynyl)phenol 1448164-84-8 C28H34O3Si2
3-((tert-butyldiphenylsilyl)oxy)-4-methoxy-5-((trimethylsilyl)ethynyl)phenol
—— 4-Hydroxy-2-methyl-5-nitrobenzolsulfonsaeure 62351-45-5 C7H7NO6S
4-Hydroxy-2-methyl-5-nitrobenzolsulfonsaeure
—— 1-(4-hydroxybenzyl)-3,3-dimethyl-1-(2-morpholinoethyl) urea 1334311-69-1 C16H25N3O3
1-(4-hydroxybenzyl)-3,3-dimethyl-1-(2-morpholinoethyl) urea
—— 1-(4-hydroxybenzyl)-3,3-dimethyl-1-(3-morpholinopropyl) urea 1348689-05-3 C17H27N3O3
1-(4-hydroxybenzyl)-3,3-dimethyl-1-(3-morpholinopropyl) urea
—— 3-methoxysalicylamine hydrochloride 141803-91-0 C8H11NO2*ClH
3-methoxysalicylamine hydrochloride
—— (1S)-N-trifluoroacetyl-1-(3-hydroxy-5-methoxy-4-methylphenyl)-2-((2-methoxyethoxy)methoxy)ethylamine 685869-29-8 C16H22F3NO6
(1S)-N-trifluoroacetyl-1-(3-hydroxy-5-methoxy-4-methylphenyl)-2-((2-methoxyethoxy)methoxy)ethylamine
—— N,N-dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276702-24-0 C8H9ClN2O5S
N,N-dimethyl-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— (4-hydroxy-3,5-dimethoxy-phenyl)-acetic acid methyl ester 151292-83-0 C11H14O5
(4-hydroxy-3,5-dimethoxy-phenyl)-acetic acid methyl ester
—— 2-fluoro-4-(3-hydroxypropyl)phenol 839694-33-6 C9H11FO2
2-fluoro-4-(3-hydroxypropyl)phenol
—— 5-Methoxy-2-(2-thiazolylazo)-phenol 15574-54-6 C10H9N3O2S
5-Methoxy-2-(2-thiazolylazo)-phenol
—— 2-oxo-thiazolidine-4-carboxylic acid (2-hydroxy-4-methoxy-phenyl)-amide 440123-52-4 C11H12N2O4S
2-oxo-thiazolidine-4-carboxylic acid (2-hydroxy-4-methoxy-phenyl)-amide