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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
—— 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
—— acetic acid-(2-hydroxy-4,6-dinitro-anilide) 860577-58-8 C8H7N3O6
acetic acid-(2-hydroxy-4,6-dinitro-anilide)
—— 2-(2-Thiazolylazo)-4-methoxy-phenol 3012-52-0 C10H9N3O2S
2-(2-Thiazolylazo)-4-methoxy-phenol
—— N-(3-Hydroxybenzyl)-N-methyl hydrazine dihydrogen phosphate 3426-07-1 C8H15N2O5P
N-(3-Hydroxybenzyl)-N-methyl hydrazine dihydrogen phosphate
—— 2-[[2-Ethoxyethyl-[(2-hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]amino]methyl]-6-methoxy-4-prop-2-enylphenol 54219-89-5 C26H35NO5
2-[[2-Ethoxyethyl-[(2-hydroxy-3-methoxy-5-prop-2-enylphenyl)methyl]amino]methyl]-6-methoxy-4-prop-2-enylphenol
—— 3-Nitro-5-amino-2-oxy-1-methyl-benzol 13478-91-6 C7H8N2O3
3-Nitro-5-amino-2-oxy-1-methyl-benzol
—— 3,4,5,6-Tetrachlorobenzene-1,2-diol;tungsten 54162-26-4 C36H12Cl24O12W2
3,4,5,6-Tetrachlorobenzene-1,2-diol;tungsten
—— 4-Chloro-2-(1-imidazol-1-yl-2-methyl-propenyl)-phenol 85128-29-6 C13H13ClN2O
4-Chloro-2-(1-imidazol-1-yl-2-methyl-propenyl)-phenol
—— 3-Fluoro-4-(1-hydroxy-2-isopropylamino-ethyl)-benzene-1,2-diol 61338-98-5 C11H16FNO3
3-Fluoro-4-(1-hydroxy-2-isopropylamino-ethyl)-benzene-1,2-diol
—— 1,5-dimethyl-3-(2'-hydroxyphenyl)-6-thioxo-1,2,4,5-tetrazane 1188549-27-0 C10H14N4OS
1,5-dimethyl-3-(2'-hydroxyphenyl)-6-thioxo-1,2,4,5-tetrazane
—— 2-amino-3,5,6-trimethyl-hydroquinone 145998-04-5 C9H13NO2
2-amino-3,5,6-trimethyl-hydroquinone
—— (2,5-dihydroxy-3,4,6-trimethyl-phenylsulfanyl)-acetic acid 792916-97-3 C11H14O4S
(2,5-dihydroxy-3,4,6-trimethyl-phenylsulfanyl)-acetic acid
—— 4-chloro-2,3,6-trimethylphenol 36433-51-9 C9H11ClO
4-chloro-2,3,6-trimethylphenol
—— seco-plakortolide M 1266187-48-7 C26H42O5
seco-plakortolide M
—— N-[3-(3,5-dimethoxy-4-hydroxybenzoylamino)propyl]-N'-[3-(3,4,5-trimethoxybenzoylamino)propyl]homopiperazine 133668-62-9 C30H44N4O8
N-[3-(3,5-dimethoxy-4-hydroxybenzoylamino)propyl]-N'-[3-(3,4,5-trimethoxybenzoylamino)propyl]homopiperazine
—— Obtusaquinone deriv jurd 2561 72590-24-0 C15H14O5
Obtusaquinone deriv jurd 2561
—— 4,6-Bis[(3-hydroxypropylamino)methyl]-2-nitrobenzene-1,3-diol 41510-33-2 C14H23N3O6
4,6-Bis[(3-hydroxypropylamino)methyl]-2-nitrobenzene-1,3-diol
—— N-(4-Chloro-2-hydroxy-benzyl)-2,2-dimethyl-propionamide 120226-57-5 C12H16ClNO2
N-(4-Chloro-2-hydroxy-benzyl)-2,2-dimethyl-propionamide
—— 4-(benzyloxy)-2-mercaptophenol 110645-14-2 C13H12O2S
4-(benzyloxy)-2-mercaptophenol
—— 4-amino-2-(2-hydroxy-3-methoxy-phenyl)-6-(4-nitro-phenyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 59623-98-2 C21H23N3O6
4-amino-2-(2-hydroxy-3-methoxy-phenyl)-6-(4-nitro-phenyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
—— 2-Methylidene-1-azabicyclo[2.2.2]octan-3-one;2,4,6-trinitrophenol 65541-32-4 C14H14N4O8
2-Methylidene-1-azabicyclo[2.2.2]octan-3-one;2,4,6-trinitrophenol