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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
—— 1-{4-[2-(6-Chloro-pyridazin-3-yloxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol 81488-57-5 C18H24ClN3O3
1-{4-[2-(6-Chloro-pyridazin-3-yloxy)-ethyl]-phenoxy}-3-isopropylamino-propan-2-ol
—— (5Z)-3-cyclohexyl-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 327054-63-7 C16H17NO3S2
(5Z)-3-cyclohexyl-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 2-(2-(3-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one 333776-51-5 C10H9N3O2S
2-(2-(3-hydroxybenzylidene)hydrazinyl)thiazol-4(5H)-one
—— 3-((Z)-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-ethyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid 1448678-46-3 C20H18N2O5S
3-((Z)-((Z)-5-(4-hydroxy-3-methoxybenzylidene)-3-ethyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid
—— Phenol, 2-bromo-6-[[(2-bromophenyl)imino]methyl]-4-chloro- 414899-38-0 C13H8Br2ClNO
Phenol, 2-bromo-6-[[(2-bromophenyl)imino]methyl]-4-chloro-
—— 1-(3-hydroxy-4-methoxybenzylidene)-4-(4-tolyl)thiosemicarbazide 316131-26-7 C16H17N3O2S
1-(3-hydroxy-4-methoxybenzylidene)-4-(4-tolyl)thiosemicarbazide
—— 3-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid —— C14H13NO5S2
3-[(5E)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
—— 2-methoxy-6-[5-(4-methoxy-phenyl)-3,4-dihydro-2<i>H</i>-pyrazol-3-yl]-phenol 58721-64-5 C17H18N2O3
2-methoxy-6-[5-(4-methoxy-phenyl)-3,4-dihydro-2<i>H</i>-pyrazol-3-yl]-phenol
—— (Z)-3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxothiazolidin-4-one 1198159-41-9 C17H12ClNO3S2
(Z)-3-(4-chlorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)-2-thioxothiazolidin-4-one
—— 4-(5-Chloro-2-hydroxy-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 79250-17-2 C13H11ClN2O2
4-(5-Chloro-2-hydroxy-phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile
—— 2-(4-hydroxy-3-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375059-00-9 C16H23N3O3S
2-(4-hydroxy-3-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-(4-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-99-3 C15H21N3O2S
2-(4-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-(3-hydroxy-4-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-96-0 C16H23N3O3S
2-(3-hydroxy-4-methoxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-(3-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one 1375058-98-2 C15H21N3O2S
2-(3-hydroxyphenyl)-3-(2-piperazin-1-ylethyl)-1,3-thiazolidin-4-one
—— 2-methoxy-4-[(2-piperazin-1-ylethylimino)methyl]phenol 1352004-93-3 C14H21N3O2
2-methoxy-4-[(2-piperazin-1-ylethylimino)methyl]phenol
—— (E)-4-fluoro-2-((2-(piperazin-1-yl)ethylimino)methyl)phenol 1246463-53-5 C13H18FN3O
(E)-4-fluoro-2-((2-(piperazin-1-yl)ethylimino)methyl)phenol
—— 2-(Pyridyl-2-amino)-4-(5-fluoro-2-hydroxy-phenyl)-thiazole 3833-85-0 C14H10FN3OS
2-(Pyridyl-2-amino)-4-(5-fluoro-2-hydroxy-phenyl)-thiazole
—— 2-(7-Furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-4-methyl-phenol 99698-72-3 C16H16N2O2
2-(7-Furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-4-methyl-phenol
—— 4-Chloro-2-(7-furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-phenol 99698-73-4 C15H13ClN2O2
4-Chloro-2-(7-furan-2-yl-2,3-dihydro-1H-[1,4]diazepin-5-yl)-phenol
—— 5-Benzyliden-3-<salicylidenamino>-rhodanin 1438-25-1 C17H12N2O2S2
5-Benzyliden-3-<salicylidenamino>-rhodanin
—— rubrolide B 136781-95-8 C17H7Br4ClO4
rubrolide B
—— 4-Pyridinecarboxamide, N-(5-((4-hydroxy-3-methoxyphenyl)methylene)-4-oxo-2-thioxo-3-thiazolidinyl)- 72732-39-9 C17H13N3O4S2
4-Pyridinecarboxamide, N-(5-((4-hydroxy-3-methoxyphenyl)methylene)-4-oxo-2-thioxo-3-thiazolidinyl)-
—— (Z)-3-(4-Hydroxy-3-methoxy-phenyl)-2-nitro-acrylonitrile 58046-27-8 C10H8N2O4
(Z)-3-(4-Hydroxy-3-methoxy-phenyl)-2-nitro-acrylonitrile
—— 146559-06-0 C19H22N2O4
—— (5E)-5-[(4-hydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one 13037-57-5 C16H11NO2S2
(5E)-5-[(4-hydroxyphenyl)methylidene]-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
—— 3-fluoro-2-nitro-6-(2-propenyl)phenol 164075-36-9 C9H8FNO3
3-fluoro-2-nitro-6-(2-propenyl)phenol
—— 4-hydroxy-N-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methoxybenzamide 5751-03-1 C19H16N2O6S2
4-hydroxy-N-[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-methoxybenzamide
—— 4-chloro-3,5,6-trimethyl-2-nitrophenol 1145874-04-9 C9H10ClNO3
4-chloro-3,5,6-trimethyl-2-nitrophenol
—— (Z)-5-((6-(4-hydroxy-3-methoxyphenyl)-2-oxoindolin-3-ylidene)methyl)-2-methylselenophene-3-carboxylic acid 1162189-86-7 C22H17NO5Se
(Z)-5-((6-(4-hydroxy-3-methoxyphenyl)-2-oxoindolin-3-ylidene)methyl)-2-methylselenophene-3-carboxylic acid
—— 4-[5-(1-imidazol-1-ylpropyl)thiophen-2-yl]phenol 1429097-58-4 C16H16N2OS
4-[5-(1-imidazol-1-ylpropyl)thiophen-2-yl]phenol
—— (4Z)-4-[(3,4-dihydroxyphenyl)methylidene]-1-(4-iodophenyl)pyrazolidine-3,5-dione 331667-56-2 C16H11IN2O4
(4Z)-4-[(3,4-dihydroxyphenyl)methylidene]-1-(4-iodophenyl)pyrazolidine-3,5-dione
—— Aethylen-bis-iminosalicyliden-diphosphonsaeure-diaethylester 36032-64-1 C20H30N2O8P2
Aethylen-bis-iminosalicyliden-diphosphonsaeure-diaethylester
—— 4-((<i>Z</i>)-3-hydroxy-benzylidene)-3-phenyl-4<i>H</i>-isoxazol-5-one 54754-44-8 C16H11NO3
4-((<i>Z</i>)-3-hydroxy-benzylidene)-3-phenyl-4<i>H</i>-isoxazol-5-one
—— (5E)-5-(3-hydroxy-4-methoxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one —— C12H11NO3S2
(5E)-5-(3-hydroxy-4-methoxybenzylidene)-3-methyl-2-thioxo-1,3-thiazolidin-4-one
—— (E)-5-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one —— C12H10BrNO3S2
(E)-5-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-3-methyl-2-thioxothiazolidin-4-one
—— asparenydiol 166762-98-7 C17H14O3
asparenydiol
—— 5-(p-hydroxyphenyl)-4-N-isopropylaminohexan-1-ol 142683-90-7 C15H25NO2
5-(p-hydroxyphenyl)-4-N-isopropylaminohexan-1-ol
—— 4-(2-(guanidino)ethyl)-phenol trifluoroacetate salt 888781-27-9 C2HF3O2*C9H13N3O
4-(2-(guanidino)ethyl)-phenol trifluoroacetate salt
—— 4-(benzyloxy)-7-(2-hydroxy-3-methoxyphenyl)-7-oxohept-5-ynal 1578203-39-0 C21H20O5
4-(benzyloxy)-7-(2-hydroxy-3-methoxyphenyl)-7-oxohept-5-ynal
—— 2-((Z)-4-Hydroxy-3-methyl-but-2-enyl)-6-methoxy-phenol 866535-23-1 C12H16O3
2-((Z)-4-Hydroxy-3-methyl-but-2-enyl)-6-methoxy-phenol
—— 5-Hydroxy-<3.3>paracyclophan 24770-04-5 C18H20O
5-Hydroxy-<3.3>paracyclophan
—— 2-p-hydroxy-m-methoxybenzylidene-3-methyl-4-nitro-3-thiolene 1,1-dioxide 106012-00-4 C13H13NO6S
2-p-hydroxy-m-methoxybenzylidene-3-methyl-4-nitro-3-thiolene 1,1-dioxide
—— N'-Isopropylidene-hydrazinecarbothioic acid S-(2,5-dihydroxy-phenyl) ester 55635-34-2 C10H12N2O3S
N'-Isopropylidene-hydrazinecarbothioic acid S-(2,5-dihydroxy-phenyl) ester
—— (3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-1-propylpiperidin-4-one 861968-04-9 C24H27NO5
(3E,5E)-3,5-bis(4-hydroxy-3-methoxybenzylidene)-1-propylpiperidin-4-one
—— Bamethan, (S)- 949926-33-4 C12H19NO2
Bamethan, (S)-
—— Bamethan, (R)- 912804-58-1 C12H19NO2
Bamethan, (R)-
—— 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodec-1-en-4-one 909281-89-6 C19H28O4
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodec-1-en-4-one
—— (5Z)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one —— C13H12BrNO3S2
(5Z)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one
—— Ethyl (3,4,5,6-tetrachloro-2-hydroxyphenyl)acetate 137676-10-9 C10H8Cl4O3
Ethyl (3,4,5,6-tetrachloro-2-hydroxyphenyl)acetate
—— (5E)-5-(5-Bromo-2-hydroxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one —— C12H10BrNO2S2
(5E)-5-(5-Bromo-2-hydroxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one