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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
—— 5-methyl-2-(phenylamino)phenol 278172-09-1 C13H13NO
5-methyl-2-(phenylamino)phenol
—— ethyl-3-(3,5-dihydroxyphenyl)butanoate 434928-72-0 C12H16O4
ethyl-3-(3,5-dihydroxyphenyl)butanoate
—— 1-[5-(3,5-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone 1428324-95-1 C17H16N2O4
1-[5-(3,5-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
—— (2-hydroxy-5-nitro-benzylimino)-di-acetic acid 115397-18-7 C11H12N2O7
(2-hydroxy-5-nitro-benzylimino)-di-acetic acid
—— <(2-hydroxy-5-nitrophenyl)methyl>phosphonic acid diethyl ester 51917-76-1 C11H16NO6P
<(2-hydroxy-5-nitrophenyl)methyl>phosphonic acid diethyl ester
—— 2,4-Dibromo-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol 1337957-42-2 C18H21Br2N3O4
2,4-Dibromo-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol
—— 2-(p-Toluol-sulfonylmethyl)-4-nitro-phenol 5804-31-9 C14H13NO5S
2-(p-Toluol-sulfonylmethyl)-4-nitro-phenol
—— N-(2-hydroxy-5-nitrobenzyl)iminodiethanol 213412-33-0 C11H16N2O5
N-(2-hydroxy-5-nitrobenzyl)iminodiethanol
—— 2,4-Dichloro-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol 1337957-41-1 C18H21Cl2N3O4
2,4-Dichloro-6-[[2-[(2-hydroxy-5-nitrophenyl)methyl-methylamino]ethyl-methylamino]methyl]phenol
—— (Z)-5-(4-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone 1314887-81-4 C17H22N2O2S2
(Z)-5-(4-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone
—— (Z)-5-(2-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone 1314887-83-6 C17H22N2O2S2
(Z)-5-(2-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone
—— 3-methyl-4-(4-thiazolyl)-5-(2-hydroxy-4-methoxyphenyl)isoxazole 82587-54-0 C14H12N2O3S
3-methyl-4-(4-thiazolyl)-5-(2-hydroxy-4-methoxyphenyl)isoxazole
—— (E)-4-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)phenol 1528690-42-7 C13H10N6OS
(E)-4-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)phenol
—— (E)-2-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)phenol 1528690-45-0 C13H10N6OS
(E)-2-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)phenol
—— 3-chloro-4-ethylphenol 1243290-06-3 C8H9ClO
3-chloro-4-ethylphenol
—— Ethyl 2-(3-hydroxy-4-methoxyphenylamino)thiazole-4-carboxylate 933045-67-1 C13H14N2O4S
Ethyl 2-(3-hydroxy-4-methoxyphenylamino)thiazole-4-carboxylate
—— 5-(2-hydroxyphenyl)-2,4-dihydro-3H-pyrazol-3-one 5186-66-3 C9H8N2O2
5-(2-hydroxyphenyl)-2,4-dihydro-3H-pyrazol-3-one
—— benzo[<i>b</i>]selenophen-5-ol 30697-17-7 C8H6OSe
benzo[<i>b</i>]selenophen-5-ol
—— (3S)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 1265355-22-3 C10H11BO5
(3S)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid
—— methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate 1265363-43-6 C10H13BO6S
methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate
—— 2-Hydroxy-4-methoxy-6-methylbenzylalkohol 70979-82-7 C9H12O3
2-Hydroxy-4-methoxy-6-methylbenzylalkohol
—— ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate 1265362-87-5 C13H17BO5
ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propanoate
—— (3R)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid 1265355-19-8 C10H11BO5
(3R)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid
—— 4-(4-phenyl-4-n-pentyl-4-silacyclohexyl)phenol 177787-30-3 C22H30OSi
4-(4-phenyl-4-n-pentyl-4-silacyclohexyl)phenol
—— (3S)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester 1265355-13-2 C12H15BO5
(3S)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester
—— (3R)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester 1265355-10-9 C12H15BO5
(3R)-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester
—— tert-butyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate 1265360-61-9 C14H19BO5
tert-butyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate
—— 5-(3',4'-Dimethoxyphenylethyl)ethyl 3-Methyl-1,4-Dihydro-2,6-dimethyl-4-(2'-trifluoromethyl)phenyl-pyridine-3,5'-dicarboxylate 887354-72-5 C27H28F3NO6
5-(3',4'-Dimethoxyphenylethyl)ethyl 3-Methyl-1,4-Dihydro-2,6-dimethyl-4-(2'-trifluoromethyl)phenyl-pyridine-3,5'-dicarboxylate
—— 2-[3-(hydroxy)benzyl]-1,2,5-thiadiazolidine 1,1-dioxide 1341126-62-2 C9H12N2O3S
2-[3-(hydroxy)benzyl]-1,2,5-thiadiazolidine 1,1-dioxide
—— 3-hydroxy-4-methoxy-2-methyl-benzaldehyde 109962-81-4 C9H10O3
3-hydroxy-4-methoxy-2-methyl-benzaldehyde
—— 4-methoxy-3,5-dipropylphenol 141988-98-9 C13H20O2
4-methoxy-3,5-dipropylphenol
—— 4,5-dimethoxy-2-(prop-2-ynyloxy)phenol 913834-28-3 C11H12O4
4,5-dimethoxy-2-(prop-2-ynyloxy)phenol
—— 2-[2,6-Bis(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-bromophenol 6776-42-7 C24H24BrN2O+
2-[2,6-Bis(4-methylphenyl)-1,2,3,4-tetrahydropyrimidin-3-ium-4-yl]-4-bromophenol
—— (-)-α,α-dideutero-m-octopamine 165460-96-8 C8H11NO2
(-)-α,α-dideutero-m-octopamine
—— 2-(N-2'-hydroxyethylmethylaminomethyl)-5-methoxyphenol 123341-20-8 C11H17NO3
2-(N-2'-hydroxyethylmethylaminomethyl)-5-methoxyphenol
—— 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-propyl-thiophen-2-yl)-propan-1-one 917873-59-7 C24H26O2S
3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(4-phenyl-5-propyl-thiophen-2-yl)-propan-1-one
—— 2-methoxy-4-(5-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-3-yl)phenol 1189742-25-3 C19H21NO6
2-methoxy-4-(5-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-3-yl)phenol
—— 2,6-dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol 1227741-04-9 C20H21NO7
2,6-dimethoxy-4-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
—— 2,6-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)phenol 1189742-26-4 C20H23NO7
2,6-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)-4,5-dihydroisoxazol-5-yl)phenol
—— 2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol 701954-74-7 C19H19NO6
2-methoxy-5-(5-(3,4,5-trimethoxyphenyl)isoxazol-3-yl)phenol
—— 2-[5-Chloro-2-hydroxy-3-(hydroxymethyl)phenyl]-3-(2-hydroxy-3-methylphenyl)-2-methyl-1,3-thiazolidin-4-one 1059562-88-7 C18H18ClNO4S
2-[5-Chloro-2-hydroxy-3-(hydroxymethyl)phenyl]-3-(2-hydroxy-3-methylphenyl)-2-methyl-1,3-thiazolidin-4-one
—— 2-[3-Chloro-2-hydroxy-5-(hydroxymethyl)phenyl]-3-(2-hydroxy-3-methylphenyl)-2-methyl-1,3-thiazolidin-4-one 1059562-69-4 C18H18ClNO4S
2-[3-Chloro-2-hydroxy-5-(hydroxymethyl)phenyl]-3-(2-hydroxy-3-methylphenyl)-2-methyl-1,3-thiazolidin-4-one
—— 4-(tetrahydropyran-3-yl)benzene-1,3-diol 1228321-23-0 C11H14O3
4-(tetrahydropyran-3-yl)benzene-1,3-diol
—— 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-2-(morpholin-4-yl)-1,3-thiazol-4(5H)-one 5853-49-6 C14H13BrN2O3S
5-[(5-Bromo-2-hydroxyphenyl)methylidene]-2-(morpholin-4-yl)-1,3-thiazol-4(5H)-one
—— 2,6-bis[bis(pyridin-2-ylmethyl)aminomethyl]-4-nitrophenol 1049723-60-5 C32H31N7O3
2,6-bis[bis(pyridin-2-ylmethyl)aminomethyl]-4-nitrophenol
—— 2-nitro-4-(perfluoropropan-2-yl)phenol 1192021-27-4 C9H4F7NO3
2-nitro-4-(perfluoropropan-2-yl)phenol
—— 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one 917873-30-4 C23H24O2S
3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one
—— 3-Fluoro-5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenol 179113-35-0 C9H5F7O2
3-Fluoro-5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenol
—— (<i>S</i>)-1-(3,4-dihydroxy-phenyl)-2-dimethylamino-ethanol 554-99-4 C10H15NO3
(<i>S</i>)-1-(3,4-dihydroxy-phenyl)-2-dimethylamino-ethanol
—— 3-ethoxy-4-(2-hydroxy-6-methylphenylamino)-cyclobut-3-ene-1,2-dione 211172-54-2 C13H13NO4
3-ethoxy-4-(2-hydroxy-6-methylphenylamino)-cyclobut-3-ene-1,2-dione