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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
—— methyl [3-(2-fluoro-4-hydroxyphenyl)-5-trifluoromethylisoxazol-4-yl]carboxylate 219939-04-5 C12H7F4NO4
methyl [3-(2-fluoro-4-hydroxyphenyl)-5-trifluoromethylisoxazol-4-yl]carboxylate
—— 3-methoxy-4-(1-trifluoromethylvinylthio)phenol 136603-73-1 C10H9F3O2S
3-methoxy-4-(1-trifluoromethylvinylthio)phenol
—— 2-methoxy-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenol 179632-69-0 C10H11F3O3
2-methoxy-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenol
—— 4-chloro-2-((E)-(isopropylimino)methyl)phenol 1268872-48-5 C10H12ClNO
4-chloro-2-((E)-(isopropylimino)methyl)phenol
—— 5-Hydroxyviloxazine 56305-63-6 C13H19NO4
5-Hydroxyviloxazine
—— (E)-1-(4-bromobenzyl)-4-(4-hydroxy-3-methoxystyryl)pyridinium bromide 1339900-05-8 Br*C21H19BrNO2
(E)-1-(4-bromobenzyl)-4-(4-hydroxy-3-methoxystyryl)pyridinium bromide
—— <i>N</i>-(3-amino-propyl)-butanediyldiamine; tripicrate 121316-68-5 3C6H3N3O7*C7H19N3
<i>N</i>-(3-amino-propyl)-butanediyldiamine; tripicrate
—— 4-(3,4-Dihydroxyphenyl)-2-(p-tolylamino)thiazole hydrochloride 17927-79-6 C16H14N2O2S*ClH
4-(3,4-Dihydroxyphenyl)-2-(p-tolylamino)thiazole hydrochloride
—— 1-(m-hydroxyphenyl)-N,N-dimethyl-2-cyclohexene-1-ethylamine 79881-61-1 C16H23NO
1-(m-hydroxyphenyl)-N,N-dimethyl-2-cyclohexene-1-ethylamine
—— Oxim v. 2-Hydroxybenzoylacetamidin 59899-12-6 C9H11N3O3
Oxim v. 2-Hydroxybenzoylacetamidin
—— 2-(6-amino-1,3-benzothiazol-2-yl)-4-methoxyphenol 664324-04-3 C14H12N2O2S
2-(6-amino-1,3-benzothiazol-2-yl)-4-methoxyphenol
—— 2-Hydroxy-3,4-dinitro-styrol 90084-99-4 C8H6N2O5
2-Hydroxy-3,4-dinitro-styrol
—— o-[4-hydroxy-3-methyl-2(Z)-butenyl]phenol 58732-18-6 C11H14O2
o-[4-hydroxy-3-methyl-2(Z)-butenyl]phenol
—— cobalt(II) 2,2'-((glutaroylbis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))diphenolate 81421-22-9 C19H18N4O4*Co
cobalt(II) 2,2'-((glutaroylbis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))diphenolate
—— 82056-88-0 C26H34Cl3MoN2O3
—— (S)-tert-butyl (2-(3-bromo-4-hydroxyphenyl)-2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate 250281-92-6 C19H32BrNO4Si
(S)-tert-butyl (2-(3-bromo-4-hydroxyphenyl)-2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate
—— 1-dichloroacetyl-3-(3'-nitro-4'-hydroxy) phenyl-1,4,5,6-tetrahydropyridazine 119837-44-4 C12H11Cl2N3O4
1-dichloroacetyl-3-(3'-nitro-4'-hydroxy) phenyl-1,4,5,6-tetrahydropyridazine
—— 2-Methoxy-(3-methoxy-4-hydroxy-benzal)-anilin 57322-39-1 C15H15NO3
2-Methoxy-(3-methoxy-4-hydroxy-benzal)-anilin
—— 2-(4-hydroxyphenyl)-5-nonyloxypyrimidine 115770-82-6 C19H26N2O2
2-(4-hydroxyphenyl)-5-nonyloxypyrimidine
—— 1,7-Bis-(2-hydroxy-3-methylphenyl)heptan 10400-44-9 C21H28O2
1,7-Bis-(2-hydroxy-3-methylphenyl)heptan
—— 1-(5-Chlor-3-nitro-2-hydroxy-benzoyl)-2-isonicotinoyl-3-(4-hydroxy-3-methoxy-phenyl)-diaziridin 100733-15-1 C21H15ClN4O7
1-(5-Chlor-3-nitro-2-hydroxy-benzoyl)-2-isonicotinoyl-3-(4-hydroxy-3-methoxy-phenyl)-diaziridin
—— rccc-2,8,14,20-tetra-iso-butyl-5,11,17,23-tetrahydroxyresorc[4]arene 246046-48-0 C44H56O12
rccc-2,8,14,20-tetra-iso-butyl-5,11,17,23-tetrahydroxyresorc[4]arene
—— 3-(2-hydroxyphenyl)-1-[16-[3-(2-hydroxyphenyl)propanoyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propan-1-one 74567-57-0 C30H42N2O8
3-(2-hydroxyphenyl)-1-[16-[3-(2-hydroxyphenyl)propanoyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]propan-1-one
—— 2,6-diformyl-p-cresol-bis(4-o-chlorophenyl thiosemicarbazone) 382141-96-0 C23H20Cl2N6OS2
2,6-diformyl-p-cresol-bis(4-o-chlorophenyl thiosemicarbazone)
—— 4,5-Dichloro-2-ethyl-phenol 52016-71-4 C8H8Cl2O
4,5-Dichloro-2-ethyl-phenol
—— 1-(2-hydroxy-3-methoxyphenyl)-2,3-diaza-4-methylthio-5-thiahexa-1,3-diene 131294-50-3 C11H14N2O2S2
1-(2-hydroxy-3-methoxyphenyl)-2,3-diaza-4-methylthio-5-thiahexa-1,3-diene
—— 3-<3-Hydroxy-2,4,6-triiodphenyl>-propionsaeure-methylester 90842-76-5 C10H9I3O3
3-<3-Hydroxy-2,4,6-triiodphenyl>-propionsaeure-methylester
—— 17646-38-7 C14H8FN5O3S
—— 1,6-Bis-(3-methoxy-4-hydroxy-phenyl)-2,5-dinitro-hexadien-(1,5) 5079-80-1 C20H20N2O8
1,6-Bis-(3-methoxy-4-hydroxy-phenyl)-2,5-dinitro-hexadien-(1,5)
—— 4-butoxy-2-chloro-phenol 671779-10-5 C10H13ClO2
4-butoxy-2-chloro-phenol
—— nickel(2+);(6Z)-4-nitro-6-[[2-[[(Z)-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]ethylamino]methylidene]cyclohexa-2,4-dien-1-one 15242-76-9 C16H14N4NiO6+2
nickel(2+);(6Z)-4-nitro-6-[[2-[[(Z)-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]ethylamino]methylidene]cyclohexa-2,4-dien-1-one
—— Trichlor-N-<2-(3,4-dihydroxyphenyl)ethyl>acetamid 69039-04-9 C10H10Cl3NO3
Trichlor-N-<2-(3,4-dihydroxyphenyl)ethyl>acetamid
—— [Pd(azido)(phenyl)(trimethylphosphine)2] 324079-94-9 C12H23N3P2Pd
[Pd(azido)(phenyl)(trimethylphosphine)2]
—— 6,6'-((cyclohexane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(4-bromo-2-nitrophenol) 943220-32-4 C20H18Br2N4O6
6,6'-((cyclohexane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(4-bromo-2-nitrophenol)
—— 2-(1-Isopropylsulfanyl-allyl)-phenol 124313-21-9 C12H16OS
2-(1-Isopropylsulfanyl-allyl)-phenol
—— 2-hydroxy-benzaldehyde (1(2)<i>H</i>-tetrazol-5-yl)-hydrazone 56929-42-1 C8H8N6O
2-hydroxy-benzaldehyde (1(2)<i>H</i>-tetrazol-5-yl)-hydrazone
—— 1-(3,5-dimethylisoxazol-4-yl)-N'-hydroxy-2-(4-hydroxyphenyl)-1H-imidazole-5-carboximidamide 1289205-09-9 C15H15N5O3
1-(3,5-dimethylisoxazol-4-yl)-N'-hydroxy-2-(4-hydroxyphenyl)-1H-imidazole-5-carboximidamide
—— (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(pyridin-3-yl)prop-2-en-1-one 76554-26-2 C16H15NO4
(E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(pyridin-3-yl)prop-2-en-1-one
—— 4-{1-hydroxy-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-ethyl}-benzene-1,2-diol 111472-49-2 C16H27N3O3
4-{1-hydroxy-2-[3-(4-methyl-piperazin-1-yl)-propylamino]-ethyl}-benzene-1,2-diol
—— 5-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)isoxazole 155721-26-9 C20H21NO8
5-(3,6-dihydroxy-2,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)isoxazole
—— 1-(R)-(3,4-dihydroxyphenyl)-2-(4-methylsulfinylbutylamino) ethanol oxalate salt 186303-23-1 C2H2O4*C13H21NO4S
1-(R)-(3,4-dihydroxyphenyl)-2-(4-methylsulfinylbutylamino) ethanol oxalate salt
—— 3-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-chloro-5-trifluoromethylisothiazole 374780-01-5 C10H3Cl2F4NOS
3-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-chloro-5-trifluoromethylisothiazole
—— 6-(4-Hydroxy-3,5-dimethoxybenzylamino)-6,7,8,9-tetrahydro-5H-benzocycloheptene 133276-35-4 C20H25NO3
6-(4-Hydroxy-3,5-dimethoxybenzylamino)-6,7,8,9-tetrahydro-5H-benzocycloheptene
—— 2-amino-5-(3,4,5-tri-hydroxy)-benzyl-mercapto-1,3,4-thiadiazole 154347-62-3 C9H9N3O3S2
2-amino-5-(3,4,5-tri-hydroxy)-benzyl-mercapto-1,3,4-thiadiazole
—— 2-(tert-butyldimethylsilyl)-4-methylphenol 1428317-36-5 C13H22OSi
2-(tert-butyldimethylsilyl)-4-methylphenol
—— 1622386-24-6 C19H20N4O8
—— Phenol, 2,6-bis(1,1-dimethylethyl)-4-[(3-hydroxy-3-methylbutyl)oxy]- 1099470-57-1 C19H32O3
Phenol, 2,6-bis(1,1-dimethylethyl)-4-[(3-hydroxy-3-methylbutyl)oxy]-
—— <i>N</i>-(5-chloro-thiazol-2-yl)-2-hydroxy-5-nitro-benzamide 74688-65-6 C10H6ClN3O4S
<i>N</i>-(5-chloro-thiazol-2-yl)-2-hydroxy-5-nitro-benzamide
—— 2,2'-((1E,1'E)-((2-((((E)-2-hydroxybenzylidene)amino)methyl)-2-((2-methoxyethoxy)methyl)propane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))diphenol 130147-62-5 C29H33N3O5
2,2'-((1E,1'E)-((2-((((E)-2-hydroxybenzylidene)amino)methyl)-2-((2-methoxyethoxy)methyl)propane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))diphenol
—— 2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)-6-methoxyphenol 1374575-89-9 C13H18O3Si
2-(1-hydroxy-3-(trimethylsilyl)prop-2-yn-1-yl)-6-methoxyphenol