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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
—— 4-hydroxy-2,6-dimethyl-3-nitro-benzonitrile 415913-74-5 C9H8N2O3
4-hydroxy-2,6-dimethyl-3-nitro-benzonitrile
—— 4-Isopentyl-pyrogallol 859208-11-0 C11H16O3
4-Isopentyl-pyrogallol
—— 2,6-diamino-1,4-dihydroxybenzene 89532-67-2 C6H8N2O2
2,6-diamino-1,4-dihydroxybenzene
—— 2-nitro-4-(pentafluorosulfanyl)phenol 1159512-26-1 C6H4F5NO3S
2-nitro-4-(pentafluorosulfanyl)phenol
—— Tetraethyl (2,5-dihydroxy-1,4-phenylene)bis(phosphonate) 91633-15-7 C14H24O8P2
Tetraethyl (2,5-dihydroxy-1,4-phenylene)bis(phosphonate)
—— 3-{5-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-propionic acid 7025-21-0 C13H11NO4S2
3-{5-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-propionic acid
—— 5-(5-chloro-2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one 6320-49-6 C10H6ClNO2S2
5-(5-chloro-2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one
—— 2-pentanyl-5-methoxyphenol 85696-82-8 C12H18O2
2-pentanyl-5-methoxyphenol
—— 2-bromo-5-fluoro-4-methoxyphenol 1185836-60-5 C7H6BrFO2
2-bromo-5-fluoro-4-methoxyphenol
—— 3-aminopyrocatechol hydrochloride 51220-97-4 C6H7NO2*ClH
3-aminopyrocatechol hydrochloride
—— 6,7,8,9-tetrahydro-5H-benzocycloheptene-2,3-diol 942-65-4 C11H14O2
6,7,8,9-tetrahydro-5H-benzocycloheptene-2,3-diol
—— 2,4-Di-iso-pentyl-phenol 93154-16-6 C16H26O
2,4-Di-iso-pentyl-phenol
—— (E)-2-(4-(2-hydroxy-3-methoxyphenyl)but-3-enyl)phenol 1325228-85-0 C17H18O3
(E)-2-(4-(2-hydroxy-3-methoxyphenyl)but-3-enyl)phenol
—— Ethyl 4-(4-hydroxy-3-iodo-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 134266-21-0 C15H17IN2O5
Ethyl 4-(4-hydroxy-3-iodo-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 1,2-Benzenediol, 4,4'-[methylenebis[sulfonyl-(1E)-2,1-ethenediyl]]bis- 312512-78-0 C17H16O8S2
1,2-Benzenediol, 4,4'-[methylenebis[sulfonyl-(1E)-2,1-ethenediyl]]bis-
—— N,N'-dimethyl-N,N'-bis[(5-methoxy-2-hydroxyphenyl)methylene]-1,2-diaminoethane 1145994-68-8 C20H28N2O4
N,N'-dimethyl-N,N'-bis[(5-methoxy-2-hydroxyphenyl)methylene]-1,2-diaminoethane
—— (2E)-3-(5-chloro-1-methyl-1H-imidazol-2-yl)-1-(2-hydroxy-4-methoxyphenyl)-2-propen-1-one 122194-00-7 C14H13ClN2O3
(2E)-3-(5-chloro-1-methyl-1H-imidazol-2-yl)-1-(2-hydroxy-4-methoxyphenyl)-2-propen-1-one
—— (Z)-methyl 3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)-propanoate 1395313-44-6 C10H10BrNO4
(Z)-methyl 3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)-propanoate
—— (4-methoxyphenyl)methyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 402502-64-1 C22H24N2O7
(4-methoxyphenyl)methyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— [2-(3-hydroxy-phenyl)-ethyl]-urea 1445847-84-6 C9H12N2O2
[2-(3-hydroxy-phenyl)-ethyl]-urea
—— 4-[(E)-{[4-(dimethylamino)phenyl]imino}methyl]benzene-1,3-diol 111279-01-7 C15H16N2O2
4-[(E)-{[4-(dimethylamino)phenyl]imino}methyl]benzene-1,3-diol
—— 2,6-Dimethyl-4-(2-methyl-2-(2-thienyl)ethenyl)phenol 142115-49-9 C15H16OS
2,6-Dimethyl-4-(2-methyl-2-(2-thienyl)ethenyl)phenol
—— 5-(p-hydroxyphenyl)pyrimidine 69491-51-6 C10H8N2O
5-(p-hydroxyphenyl)pyrimidine
—— 4-((benzylimino)methyl)benzene-1,3-diol 215232-61-4 C14H13NO2
4-((benzylimino)methyl)benzene-1,3-diol
—— 5-ethoxycarbonyl-6-methyl-4(4-hydroxy-3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one 299407-35-5 C14H15N3O6
5-ethoxycarbonyl-6-methyl-4(4-hydroxy-3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
—— 2-(1-(3-methylamino-propylamino)-ethyl)-phenol 1350294-83-5 C12H20N2O
2-(1-(3-methylamino-propylamino)-ethyl)-phenol
—— 2,4-dihydroxy-benzaldehyde imine 5660-21-9 C7H7NO2
2,4-dihydroxy-benzaldehyde imine
—— diethyl 3-decyl-2-hydroxybenzenephosphonate 144381-68-0 C20H35O4P
diethyl 3-decyl-2-hydroxybenzenephosphonate
—— (E)-3-((2-hydroxybenzylidene)amino)-2-thioxothiazolidin-4-one 1621252-79-6 C10H8N2O2S2
(E)-3-((2-hydroxybenzylidene)amino)-2-thioxothiazolidin-4-one
—— 2,3,4-trichloro-5-methoxy-phenol 98273-26-8 C7H5Cl3O2
2,3,4-trichloro-5-methoxy-phenol
—— 3-(4-hydroxybenzylideneamino)-2-thioxothiazolidin-4-one 90771-12-3 C10H8N2O2S2
3-(4-hydroxybenzylideneamino)-2-thioxothiazolidin-4-one
—— 3-amino-2-thioxo-5-vanillylidene-thiazolidin-4-one 99985-11-2 C11H10N2O3S2
3-amino-2-thioxo-5-vanillylidene-thiazolidin-4-one
—— (E)-3-(4-hydroxy-3,5-dimethoxybenzylideneamino)-2-thioxothiazolidin-4-one 1621252-77-4 C12H12N2O4S2
(E)-3-(4-hydroxy-3,5-dimethoxybenzylideneamino)-2-thioxothiazolidin-4-one
—— (Z)-3-amino-5-(3',5'-diiodo-4'-hydroxybenzylidene)-2-thioxothiazolidin-4-one 1133953-95-3 C10H6I2N2O2S2
(Z)-3-amino-5-(3',5'-diiodo-4'-hydroxybenzylidene)-2-thioxothiazolidin-4-one
—— (Z)-3-amino-5-(4'-hydroxybenzylidene)-2-thioxothiazolidin-4-one 1133953-97-5 C10H8N2O2S2
(Z)-3-amino-5-(4'-hydroxybenzylidene)-2-thioxothiazolidin-4-one
—— 4H-Imidazol-4-one, 3,5-dihydro-5-((4-hydroxy-3-methoxyphenyl)methylene)-2-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)- 76834-44-1 C15H14N4O3S
4H-Imidazol-4-one, 3,5-dihydro-5-((4-hydroxy-3-methoxyphenyl)methylene)-2-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-
—— 3-[(2-hydroxy-3,5-dibromophen-1-yl)methyleneamino]-2-thioxothiazolidin-4-one 340041-28-3 C10H6Br2N2O2S2
3-[(2-hydroxy-3,5-dibromophen-1-yl)methyleneamino]-2-thioxothiazolidin-4-one
—— 3,4,5-trihydroxy-benzaldehyde-oxime 53148-14-4 C7H7NO4
3,4,5-trihydroxy-benzaldehyde-oxime
—— 1-(3,5-bis(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 1428324-88-2 C17H16N2O3
1-(3,5-bis(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
—— 4-amino-5-methyl-pyrocatechol 749819-92-9 C7H9NO2
4-amino-5-methyl-pyrocatechol
—— 2,2'-trisulfanediyl-di-phenol 100953-03-5 C12H10O2S3
2,2'-trisulfanediyl-di-phenol
—— 2,6-di-butylphenol 62083-20-9 C14H22O
2,6-di-butylphenol
—— 4-butyl-2-chloro-phenol 18980-02-4 C10H13ClO
4-butyl-2-chloro-phenol
—— 1-(2'-hydroxy-5'-butylphenyl)-1-ethanone (E)-oxime 103582-33-8 C12H17NO2
1-(2'-hydroxy-5'-butylphenyl)-1-ethanone (E)-oxime
—— ethyl (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylate 906802-40-2 C19H28O5
ethyl (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylate
—— 2-(2-amino-thiazol-4-yl)-4-fluoro-phenol 23226-04-2 C9H7FN2OS
2-(2-amino-thiazol-4-yl)-4-fluoro-phenol
—— 6-Ethyl-3-methyl-p-Chlorophenol 18980-09-1 C9H11ClO
6-Ethyl-3-methyl-p-Chlorophenol
—— 4-(4-hydroxy-3-methoxyphenyl)-N,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 433317-60-3 C14H17N3O3S
4-(4-hydroxy-3-methoxyphenyl)-N,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
—— 4-(2-hydroxy-3-methoxyphenyl)-N,6-dimethyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide 141353-97-1 C14H17N3O4
4-(2-hydroxy-3-methoxyphenyl)-N,6-dimethyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
—— 4-(2-hydroxy-3-methoxyphenyl)-N,6-dimethyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide 141354-10-1 C14H17N3O3S
4-(2-hydroxy-3-methoxyphenyl)-N,6-dimethyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide