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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
—— 4,4’-(pentane-1,5-diyl)bis(benzene-1,2-diol) 83644-01-3 C17H20O4
4,4’-(pentane-1,5-diyl)bis(benzene-1,2-diol)
—— N-(4-Hydroxy-3-methoxybenzyl)-6-methylheptamide 61229-10-5 C16H25NO3
N-(4-Hydroxy-3-methoxybenzyl)-6-methylheptamide
—— 2,2,5,5-tetramethyl-3-(3-nitro-4-hydroxybenzoyl)-3-pyrrolin-1-oxyl 124190-10-9 C15H17N2O5
2,2,5,5-tetramethyl-3-(3-nitro-4-hydroxybenzoyl)-3-pyrrolin-1-oxyl
—— 3-(1-bromo-2-hydroxypent-4-en-2-yl)phenol 1450629-59-0 C11H13BrO2
3-(1-bromo-2-hydroxypent-4-en-2-yl)phenol
—— 124558-33-4 C17H20NO4
—— 124558-32-3 C17H20NO4
—— 3-(bromoethynyl)phenol 1370031-23-4 C8H5BrO
3-(bromoethynyl)phenol
—— 2-Bromo-4-(1,1,2,2-tetrafluoroethoxy)phenol 89227-92-9 C8H5BrF4O2
2-Bromo-4-(1,1,2,2-tetrafluoroethoxy)phenol
—— 2-chloro-4,6-dinitroresorcinol 116920-31-1 C6H3ClN2O6
2-chloro-4,6-dinitroresorcinol
—— 3-{[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]carbonyl}-5-methylphenol 1619982-81-8 C22H30O2
3-{[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]carbonyl}-5-methylphenol
—— 4-methyl-2,6-bis(pyrazol-1-ylmethyl)phenol 135961-79-4 C15H16N4O
4-methyl-2,6-bis(pyrazol-1-ylmethyl)phenol
—— (2E,4E)-1-(2-hydroxy-5-methylphenyl)-5-phenyl-2,4-pentadiene-1-one 136054-87-0 C18H16O2
(2E,4E)-1-(2-hydroxy-5-methylphenyl)-5-phenyl-2,4-pentadiene-1-one
—— 4-(3-Dimethylamino-butyl)-phenol 126521-62-8 C12H19NO
4-(3-Dimethylamino-butyl)-phenol
—— 2-Chloro-4-(2-chloro-1,1,2-trifluoroethoxy)phenol 88553-92-8 C8H5Cl2F3O2
2-Chloro-4-(2-chloro-1,1,2-trifluoroethoxy)phenol
—— 2-Chloro-4-(1,1,2,2-tetrafluoroethoxy)phenol 88553-91-7 C8H5ClF4O2
2-Chloro-4-(1,1,2,2-tetrafluoroethoxy)phenol
—— 4-bromo-5-nitro-pyrocatechol 52864-93-4 C6H4BrNO4
4-bromo-5-nitro-pyrocatechol
—— 2-Bromo-4-(2-chloro-1,1,2-trifluoroethoxy)phenol 89227-94-1 C8H5BrClF3O2
2-Bromo-4-(2-chloro-1,1,2-trifluoroethoxy)phenol
—— 1,3-dihydroxy-1-(3-hydroxyphenyl)propan-2-one 1256696-41-9 C9H10O4
1,3-dihydroxy-1-(3-hydroxyphenyl)propan-2-one
—— 4-(2-Bromo-1,1,2-trifluoroethoxy)phenol 88553-86-0 C8H6BrF3O2
4-(2-Bromo-1,1,2-trifluoroethoxy)phenol
—— 5-(2,5-dihydroxy-3,4,6-trichlorophenyl)-3-methylthiazoline-2-thione 159262-80-3 C10H6Cl3NO2S2
5-(2,5-dihydroxy-3,4,6-trichlorophenyl)-3-methylthiazoline-2-thione
—— 2-Methoxy-4-[(2-methoxy-4-methylphenoxy)methyl]phenol 90139-54-1 C16H18O4
2-Methoxy-4-[(2-methoxy-4-methylphenoxy)methyl]phenol
—— 4-{3-[(4-Hydroxy-3-methoxyphenyl)methoxy]propyl}-2-methoxyphenol 90139-55-2 C18H22O5
4-{3-[(4-Hydroxy-3-methoxyphenyl)methoxy]propyl}-2-methoxyphenol
—— 2-hydroxy-5-fluorobenzylacetone 1019769-63-1 C10H11FO2
2-hydroxy-5-fluorobenzylacetone
—— 2-(2,2-dichloro-acetylamino)-4-methyl-phenol 72805-08-4 C9H9Cl2NO2
2-(2,2-dichloro-acetylamino)-4-methyl-phenol
—— 1-(3-(2,4-dihydroxyphenyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 55370-72-4 C17H16N2O4
1-(3-(2,4-dihydroxyphenyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one
—— 5-ethyl-6-(4-hydroxyphenyl)-8,9-dihydro-7H-benzocyclohepten-2-ol 1143508-23-9 C19H20O2
5-ethyl-6-(4-hydroxyphenyl)-8,9-dihydro-7H-benzocyclohepten-2-ol
—— 4-chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol 1134914-68-3 C15H12Cl2F3NO2
4-chloro-3-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol
—— (Z)-2-(3-hydroxy-4-methoxybenzylidene)indolin-3-one 1148119-21-4 C16H13NO3
(Z)-2-(3-hydroxy-4-methoxybenzylidene)indolin-3-one
—— 1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-yl)ethanone 1472645-95-6 C18H19N3O3
1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-phenyl-4,5-dihydropyrazol-1-yl)ethanone
—— 3-[1-(Prop-2-en-1-yl)-1,2,5,6-tetrahydropyridin-3-yl]phenol 83010-62-2 C14H17NO
3-[1-(Prop-2-en-1-yl)-1,2,5,6-tetrahydropyridin-3-yl]phenol
—— (Z)1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)-prop-2-en-1-one 1379535-63-3 C19H20BrNO6
(Z)1-(2-bromo-3,4,5-trimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenylamino)-prop-2-en-1-one
—— 3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[3-(3-bromo-4-hydroxyphenyl)-2-oxopropanoyl]amino]ethyldisulfanyl]ethyl]-2-oxopropanamide 1356929-88-8 C22H22Br2N2O6S2
3-(3-bromo-4-hydroxyphenyl)-N-[2-[2-[[3-(3-bromo-4-hydroxyphenyl)-2-oxopropanoyl]amino]ethyldisulfanyl]ethyl]-2-oxopropanamide
—— 1-(5-(3-amino-4-hydroxy-5-chlorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl)ethanone 1472646-01-7 C17H16ClN3O2
1-(5-(3-amino-4-hydroxy-5-chlorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl)ethanone
—— (2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-fluoro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] 1314789-52-0 C22H24F2N4O6S2
(2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-fluoro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)propanamide] 1314789-15-5 C22H26Br2N2O4S2
N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)propanamide]
—— 2-Hydroxy-4-chlorphenylacetylen 36739-98-7 C8H5ClO
2-Hydroxy-4-chlorphenylacetylen
—— 1,2-bis(tert-butoxycarbonyl)-1-(3-bromo-4-hydroxybenzyl)guanidine —— C18H26BrN3O5
1,2-bis(tert-butoxycarbonyl)-1-(3-bromo-4-hydroxybenzyl)guanidine
—— 4-[(E)-[(5-phenyl-1,3,4-thiadiazol-2-yl)hydrazinylidene]methyl]benzene-1,2-diol 1274816-42-0 C15H12N4O2S
4-[(E)-[(5-phenyl-1,3,4-thiadiazol-2-yl)hydrazinylidene]methyl]benzene-1,2-diol
—— 2-bromo-3,5-dihydroxy-4-methoxybenzaldehyde 1000404-16-9 C8H7BrO4
2-bromo-3,5-dihydroxy-4-methoxybenzaldehyde
—— 4-[(E)-[(5-phenyl-1,3,4-thiadiazol-2-yl)hydrazinylidene]methyl]phenol 1272066-07-5 C15H12N4OS
4-[(E)-[(5-phenyl-1,3,4-thiadiazol-2-yl)hydrazinylidene]methyl]phenol
—— 3-methyl-6-(2-methylpropenyl)benzene-1,2-diol 502506-95-8 C11H14O2
3-methyl-6-(2-methylpropenyl)benzene-1,2-diol
—— 4-[5-[4-[5-(4-Hydroxyphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazol-2-yl]phenol 181766-12-1 C22H14N4O4
4-[5-[4-[5-(4-Hydroxyphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazol-2-yl]phenol
—— E-acetic acid 2-acetoxy-4-[2-(4-phenylbutane-1-sulfinyl)vinyl]phenyl ester 1609008-02-7 C18H20O3S
E-acetic acid 2-acetoxy-4-[2-(4-phenylbutane-1-sulfinyl)vinyl]phenyl ester
—— N,N-Diacetyl-2-(2,5-dihydroxy-4-methyl-phenyl)-ethylamin 116626-45-0 C13H17NO4
N,N-Diacetyl-2-(2,5-dihydroxy-4-methyl-phenyl)-ethylamin
—— N-Acetyl-N-methyl-2-(2,5-dihydroxy-4-methyl-phenyl)-ethylamin 116626-51-8 C12H17NO3
N-Acetyl-N-methyl-2-(2,5-dihydroxy-4-methyl-phenyl)-ethylamin
—— N-[3-(2,5-dihydroxy-4-methylphenyl)propyl]-N-methylacetamide 121746-37-0 C13H19NO3
N-[3-(2,5-dihydroxy-4-methylphenyl)propyl]-N-methylacetamide
—— (E)-4-[2-((4-phenylbut-1-yl)sulfonyl)vinyl]benzene-1,2-diol 1609007-94-4 C18H20O4S
(E)-4-[2-((4-phenylbut-1-yl)sulfonyl)vinyl]benzene-1,2-diol
—— 4-((4-hydroxyphenylimino)methyl)benzene-1,3-diol 111279-02-8 C13H11NO3
4-((4-hydroxyphenylimino)methyl)benzene-1,3-diol
—— (4R)-5-(3-hydroxyphenyl)-γ-valerolactone 191666-23-6 C11H12O3
(4R)-5-(3-hydroxyphenyl)-γ-valerolactone
—— 5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazole-1-carbaldehyde 1253978-22-1 C11H12N2O2
5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazole-1-carbaldehyde