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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
—— Bicyclo[9.3.1]pentadeca-1(15),11,13-trien-15-ol 38660-82-1 C15H22O
Bicyclo[9.3.1]pentadeca-1(15),11,13-trien-15-ol
—— 6-allyl-2-iodophenol 54826-57-2 C9H9IO
6-allyl-2-iodophenol
—— 3-pentadeca-8,11-dienylphenol 31910-56-2 C21H32O
3-pentadeca-8,11-dienylphenol
—— 13-(2-hydroxyphenyl)-4-carboxy[2.2]paracyclophane 588717-77-5 C23H20O3
13-(2-hydroxyphenyl)-4-carboxy[2.2]paracyclophane
—— 4-hydroxymethyl-13-(2-hydroxyphenyl)-[2.2]paracyclopane 588717-78-6 C23H22O2
4-hydroxymethyl-13-(2-hydroxyphenyl)-[2.2]paracyclopane
—— 15-hydroxymethyl[2.2]paracyclophan-4-ol 600143-72-4 C17H18O2
15-hydroxymethyl[2.2]paracyclophan-4-ol
—— N-[2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide 1374640-38-6 C14H21NO3
N-[2-(4-hydroxyphenyl)ethyl]-2-hydroxy-4-methylpentanamide
—— 2-dodecyl-4-chlorophenol 1115234-54-2 C18H29FO
2-dodecyl-4-chlorophenol
—— 1-[4-(2-Hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethan-1-one 5118-42-3 C13H13N3O4S
1-[4-(2-Hydroxy-5-nitrophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethan-1-one
—— 4-[(2-hydroxy-5-nitrobenzylidene)amino]benzoic acid 184715-33-1 C14H10N2O5
4-[(2-hydroxy-5-nitrobenzylidene)amino]benzoic acid
—— 2-methoxy-5-<<(4-nitrophenyl)imino>methyl>phenol 115095-32-4 C14H12N2O4
2-methoxy-5-<<(4-nitrophenyl)imino>methyl>phenol
—— 4-Methyl-2-octyl-phenol 886-00-0 C15H24O
4-Methyl-2-octyl-phenol
—— 5-acetyl-4-(4-hydroxyphenyl)-2-carbamoyl-ethylsulfanyl-1,4-dihydropyridine-3-carbonitrile 5314-25-0 C17H17N3O3S
5-acetyl-4-(4-hydroxyphenyl)-2-carbamoyl-ethylsulfanyl-1,4-dihydropyridine-3-carbonitrile
—— Prop-2-en-1-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 5477-51-0 C16H18N2O5
Prop-2-en-1-yl 4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— N-<β-(4-Hydroxyphenylethyl>-1-adamantancarboxamid 42600-86-2 C19H25NO2
N-<β-(4-Hydroxyphenylethyl>-1-adamantancarboxamid
—— (5Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one 331711-38-7 C11H8BrNO3S2
(5Z)-5-(3-Bromo-2-hydroxy-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
—— 2-methyl-6-octylphenol 17901-33-6 C15H24O
2-methyl-6-octylphenol
—— 4-bromo-3-trimethylsilylphenol 17878-46-5 C9H13BrOSi
4-bromo-3-trimethylsilylphenol
—— methyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 5466-83-1 C14H15ClN2O5
methyl 4-(3-chloro-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 2-Methyl-4-octyl-phenol 5075-81-0 C15H24O
2-Methyl-4-octyl-phenol
—— 5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one 99985-06-5 C11H10N2O3S
5-[(4-Hydroxy-3-methoxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
—— 1,3-Benzenediol, 4-(1,2,3,6-tetrahydro-2,2,6,6-tetramethyl-4-pyridinyl)- 90747-13-0 C15H21NO2
1,3-Benzenediol, 4-(1,2,3,6-tetrahydro-2,2,6,6-tetramethyl-4-pyridinyl)-
—— diphenyl (2,5-dihydroxyphenyl)phosphonate 1384457-19-5 C18H15O5P
diphenyl (2,5-dihydroxyphenyl)phosphonate
—— 5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one 359899-47-1 C13H12BrNO3S2
5-[(5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene]-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— Ethyl (8Z)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-2-(4-methylphenyl)-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate 5667-90-3 C25H24N2O5S
Ethyl (8Z)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-2-(4-methylphenyl)-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate
—— Ethyl (8Z)-2-(3,4-dimethoxyphenyl)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate 5679-64-1 C26H26N2O7S
Ethyl (8Z)-2-(3,4-dimethoxyphenyl)-8-[(4-hydroxy-3-methoxy-phenyl)methylidene]-4-methyl-9-oxo-7-thia-1,5-diazabicyclo[4.3.0]nona-3,5-diene-3-carboxylate
—— 3-bromo-2-hydroxy-6-methoxybenzaldehyde 29866-53-3 C8H7BrO3
3-bromo-2-hydroxy-6-methoxybenzaldehyde
—— 4-hydroxyphenyl-N,N-dimethylimide 33709-30-7 C9H11NO
4-hydroxyphenyl-N,N-dimethylimide
—— 1,2-Dimethoxy-4-[2-(methoxymethoxy)ethyl]benzene 1338236-55-7 C12H18O4
1,2-Dimethoxy-4-[2-(methoxymethoxy)ethyl]benzene
—— 4-chloro-2-[(3-dimethylaminopropylimino)methyl]phenol 1489230-36-5 C12H17ClN2O
4-chloro-2-[(3-dimethylaminopropylimino)methyl]phenol
—— 2-tert-butyl-4-fluoro-5-nitrophenol 873055-44-8 C10H12FNO3
2-tert-butyl-4-fluoro-5-nitrophenol
—— (E)-3-(3-hydroxy-4-methoxybenzylidene)-1-methylindolin-2-one 1148119-20-3 C17H15NO3
(E)-3-(3-hydroxy-4-methoxybenzylidene)-1-methylindolin-2-one
—— ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 5832-47-3 C25H23BrN2O6S
ethyl 2-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylidene]-5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol 868849-46-1 C14H21NO2
4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol
—— methyl [2-(3,5-dibromo-4-hydroxyphenyl)ethyl]carbamate 62372-09-2 C10H11Br2NO3
methyl [2-(3,5-dibromo-4-hydroxyphenyl)ethyl]carbamate
—— tert-butyl (2-hydroxy-1-(3-hydroxyphenyl)ethyl)carbamate 1454273-67-6 C13H19NO4
tert-butyl (2-hydroxy-1-(3-hydroxyphenyl)ethyl)carbamate
—— Tert-butyl [3-hydroxy-2-methyl-4-(3-methylbutyl)phenyl] carbonate 679433-33-1 C17H26O4
Tert-butyl [3-hydroxy-2-methyl-4-(3-methylbutyl)phenyl] carbonate
—— 2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate 1159795-87-5 C18H29BrO5Si
2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate
—— (2-{N'-[1-(3-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-oxo-4,5-dihydro-thiazol-5-yl)-acetic acid 21938-65-8 C12H11N3O4S
(2-{N'-[1-(3-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-oxo-4,5-dihydro-thiazol-5-yl)-acetic acid
—— 1-(3-hydroxy-phenyl)-nonadecan-2-one 501-09-7 C25H42O2
1-(3-hydroxy-phenyl)-nonadecan-2-one
—— 5-methyl-thiophene-2-carbaldehyde-(4-hydroxy-phenylimine) 91569-00-5 C12H11NOS
5-methyl-thiophene-2-carbaldehyde-(4-hydroxy-phenylimine)
—— 4-tert-butyl-2-chloro-5-nitrophenol 873055-60-8 C10H12ClNO3
4-tert-butyl-2-chloro-5-nitrophenol
—— 4-dimethylaminomethyl-2,6-dimethylphenol 83037-96-1 C10H15NO
4-dimethylaminomethyl-2,6-dimethylphenol
—— 2-{(E)-[(5-Methylthiophen-2-yl)methylidene]amino}-4-nitrophenol 60957-41-7 C12H10N2O3S
2-{(E)-[(5-Methylthiophen-2-yl)methylidene]amino}-4-nitrophenol
—— 2-Hydroxy-5-methoxy-3-methylbenzylalkohol 5600-81-7 C9H12O3
2-Hydroxy-5-methoxy-3-methylbenzylalkohol
—— 2-[(1H-benzimidazol-2-ylhydrazinylidene)methyl]-4-methoxyphenol 130880-01-2 C15H14N4O2
2-[(1H-benzimidazol-2-ylhydrazinylidene)methyl]-4-methoxyphenol
—— 2-[[4-[(3-Chlorophenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol 6108-09-4 C19H23ClN2O2
2-[[4-[(3-Chlorophenyl)methyl]piperazin-1-yl]methyl]-4-methoxyphenol
—— ethyl 4-(5-chloro-2-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 6375-59-3 C15H17ClN2O5
ethyl 4-(5-chloro-2-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
—— 3-Chloro-6-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]pyridazine 160951-24-6 C15H15ClN2O3
3-Chloro-6-[2-[4-(oxiran-2-ylmethoxy)phenyl]ethoxy]pyridazine
—— Ethyl 2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate 6173-07-5 C21H17BrN2O4S2
Ethyl 2-[(3-bromo-4-hydroxyphenyl)methylidene]-7-methyl-3-oxo-5-(thiophen-2-yl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate