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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
—— 4,6-dichloro-N-cyclopropylmethyl-3-hydroxy-2-nitrobenzamide 1232842-32-8 C11H10Cl2N2O4
4,6-dichloro-N-cyclopropylmethyl-3-hydroxy-2-nitrobenzamide
—— 1H-4,5-dihydro-3-methyl-5-(4-hydroxyphenyl)pyrazole 200417-33-0 C10H12N2O
1H-4,5-dihydro-3-methyl-5-(4-hydroxyphenyl)pyrazole
—— N-(cyclopropylmethyl)-11-(3,5-dihydroxyphenoxy)undecanamide 1150586-67-6 C21H33NO4
N-(cyclopropylmethyl)-11-(3,5-dihydroxyphenoxy)undecanamide
—— (3-bromo-4-hydroxy-benzyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester 865539-49-7 C17H26BrNO3
(3-bromo-4-hydroxy-benzyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester
—— 11-(3,5-Dihydroxyphenoxy)undecanoic acid 1150586-46-1 C17H26O5
11-(3,5-Dihydroxyphenoxy)undecanoic acid
—— 2-(Benzylideneamino)-5-(3-hydroxy-4-nitrophenyl)selanylphenol 1246255-30-0 C19H14N2O4Se
2-(Benzylideneamino)-5-(3-hydroxy-4-nitrophenyl)selanylphenol
—— 4-[(2,2,3,3,4,4,5,5-Octafluoropentylamino)methylidene]cyclohexa-2,5-dien-1-one 5320-11-6 C12H9F8NO
4-[(2,2,3,3,4,4,5,5-Octafluoropentylamino)methylidene]cyclohexa-2,5-dien-1-one
—— 2-(4-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethoxy}-phenoxy)-N-methyl-acetamide 102528-01-8 C20H26N2O6
2-(4-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethoxy}-phenoxy)-N-methyl-acetamide
—— 5-n-pentadecyl-2-nitrophenol 200421-95-0 C21H35NO3
5-n-pentadecyl-2-nitrophenol
—— 4-methyl-3-(5-methylhex-4-en-1-yl)phenol 1314095-88-9 C14H20O
4-methyl-3-(5-methylhex-4-en-1-yl)phenol
—— 4-(2-methyl-5-hydroxyphenyl)butanal 97400-51-6 C11H14O2
4-(2-methyl-5-hydroxyphenyl)butanal
—— 2,4,6-trimethyl-3-(5-methylhex-4-en-1-yl)phenol 1314095-94-7 C16H24O
2,4,6-trimethyl-3-(5-methylhex-4-en-1-yl)phenol
—— 4-(3-hydroxy-2,4,6-trimethylphenyl)butanal 1029654-59-8 C13H18O2
4-(3-hydroxy-2,4,6-trimethylphenyl)butanal
—— N-nitrozo(m-hydroxybenzyl)methylamine 90271-38-8 C8H10N2O2
N-nitrozo(m-hydroxybenzyl)methylamine
—— 2-benzylideneamino-4,6-dinitro-phenol 53088-06-5 C13H9N3O5
2-benzylideneamino-4,6-dinitro-phenol
—— (5Z)-5-(3-hydroxybenzylidene)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4(5H)-one 5954-01-8 C16H18N2O2S
(5Z)-5-(3-hydroxybenzylidene)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4(5H)-one
—— Phenol, 2-[[[2-(3,4-dimethoxyphenyl)ethyl]imino]methyl]-4-nitro- 88307-66-8 C17H18N2O5
Phenol, 2-[[[2-(3,4-dimethoxyphenyl)ethyl]imino]methyl]-4-nitro-
—— (5E)-3-(3-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 292075-72-0 C16H10ClNO3S2
(5E)-3-(3-chlorophenyl)-5-[(3,4-dihydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
—— 4,4'-(dipropylsilanediyl)bis(2-methylphenol) 1595163-99-7 C20H28O2Si
4,4'-(dipropylsilanediyl)bis(2-methylphenol)
—— 2-methoxy-4-(5-morpholin-4-yl-penta-1,3-diynyl)-phenol 33834-18-3 C16H17NO3
2-methoxy-4-(5-morpholin-4-yl-penta-1,3-diynyl)-phenol
—— (E)-5-(5-Bromo-2-hydroxybenzylidene)-3-ethyl-2-thioxothiazolidin-4-one —— C12H10BrNO2S2
(E)-5-(5-Bromo-2-hydroxybenzylidene)-3-ethyl-2-thioxothiazolidin-4-one
—— 5-chloro-3-methyl-benzene-1,2,4-triol 871880-92-1 C7H7ClO3
5-chloro-3-methyl-benzene-1,2,4-triol
—— (4Z)-4-[(2-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione 4590-83-4 C16H12N2O3
(4Z)-4-[(2-hydroxyphenyl)methylidene]-1-phenylpyrazolidine-3,5-dione
—— (5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one —— C13H12BrNO3S2
(5E)-5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-3-ethyl-2-thioxo-1,3-thiazolidin-4-one
—— 2-amino-1-(3-hydroxy-phenyl)-butan-1-ol 20738-08-3 C10H15NO2
2-amino-1-(3-hydroxy-phenyl)-butan-1-ol
—— 5-(3,4-Dihydroxybenzylidene)-3-(4-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one 356570-17-7 C16H11NO4S2
5-(3,4-Dihydroxybenzylidene)-3-(4-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one
—— 2-nitro-4-(trifluoromethylsulfinyl)phenol 1616682-58-6 C7H4F3NO4S
2-nitro-4-(trifluoromethylsulfinyl)phenol
—— (E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(pyridine-3-yl)prop-2-en-1-one 1335009-29-4 C16H14BrNO4
(E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(pyridine-3-yl)prop-2-en-1-one
—— 1-(4-hydroxy-3,5-dimethoxy-phenyl)-2,6-dimethyl-4-oxo-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 856859-13-7 C21H25NO8
1-(4-hydroxy-3,5-dimethoxy-phenyl)-2,6-dimethyl-4-oxo-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
—— (R)-5-(1-(3-hydroxyphenyl)-3-(trimethylsilyl)prop-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 1189171-00-3 C18H22O5Si
(R)-5-(1-(3-hydroxyphenyl)-3-(trimethylsilyl)prop-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
—— (2E,4Z)-5-chloro-5-(2-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-39-5 C19H16Cl2O4
(2E,4Z)-5-chloro-5-(2-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
—— 3-(2-furyl)-2'-hydroxy-4',6'-dimethoxyacrylophenone 24933-85-5 C15H14O5
3-(2-furyl)-2'-hydroxy-4',6'-dimethoxyacrylophenone
—— 5-hydroxy-2-nitro-N-pyridin-2-ylbenzamide 1616693-68-5 C12H9N3O4
5-hydroxy-2-nitro-N-pyridin-2-ylbenzamide
—— (2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-p-tolylpenta-2,4-dien-1-one 1227403-47-5 C20H19ClO4
(2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-p-tolylpenta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-5-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-41-9 C19H16Cl2O4
(2E,4Z)-5-chloro-5-(4-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(3-methoxyphenyl)-penta-2,4-dien-1-one 1227403-48-6 C20H19ClO5
(2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(3-methoxyphenyl)-penta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(3,5-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-45-3 C21H21ClO6
(2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(3,5-dimethoxyphenyl)penta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-5-(2,4-dichlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-46-4 C19H15Cl3O4
(2E,4Z)-5-chloro-5-(2,4-dichlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
—— 4,7-dihydroxy-1,3-benzodithiole-2-thione 53636-07-0 C7H4O2S3
4,7-dihydroxy-1,3-benzodithiole-2-thione
—— (2E,4Z)-5-(4-bromophenyl)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-38-4 C19H16BrClO4
(2E,4Z)-5-(4-bromophenyl)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(4-methoxyphenyl)penta-2,4-dien-1-one 1227403-43-1 C20H19ClO5
(2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(4-methoxyphenyl)penta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-5-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-40-8 C19H16Cl2O4
(2E,4Z)-5-chloro-5-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
—— (2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(2,4-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-44-2 C21H21ClO6
(2E,4Z)-5-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)-5-(2,4-dimethoxyphenyl)penta-2,4-dien-1-one
—— 3-(Thiophene)-2-yl-1-(2-hydroxy-4,6-dimethoxyphenyl)-prop-2-en-1-one 76554-36-4 C15H14O4S
3-(Thiophene)-2-yl-1-(2-hydroxy-4,6-dimethoxyphenyl)-prop-2-en-1-one
—— 2-chloro-4-((6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl)methyl)phenol 1399857-72-7 C17H11ClFN5O
2-chloro-4-((6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl)methyl)phenol
—— (1R,3R,4R)-1,4-bis(tert-butyldimethylsilyloxy)-5-(3-hydroxyphenyl)cyclohex-5-ene-1,3-carbolactone 862791-44-4 C25H40O5Si2
(1R,3R,4R)-1,4-bis(tert-butyldimethylsilyloxy)-5-(3-hydroxyphenyl)cyclohex-5-ene-1,3-carbolactone
—— (1R,3R,4R)-1,4-dihydroxy-5-(3-hydroxyphenyl)cyclohex-5-ene-1,3-carbolactone 862791-77-3 C13H12O5
(1R,3R,4R)-1,4-dihydroxy-5-(3-hydroxyphenyl)cyclohex-5-ene-1,3-carbolactone
—— (4Z)-4-[(4-hydroxy-3-nitrophenyl)methylidene]-1-(4-methylphenyl)pyrazolidine-3,5-dione 5839-31-6 C17H13N3O5
(4Z)-4-[(4-hydroxy-3-nitrophenyl)methylidene]-1-(4-methylphenyl)pyrazolidine-3,5-dione
—— (5E)-3-prop-2-enyl-2-sulfanylidene-5-[(2,4,6-trichloro-3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one 6523-13-3 C13H8Cl3NO2S2
(5E)-3-prop-2-enyl-2-sulfanylidene-5-[(2,4,6-trichloro-3-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (R)-3-ethyl-2-(1-hydroxyallyl)phenol 909532-76-9 C11H14O2
(R)-3-ethyl-2-(1-hydroxyallyl)phenol