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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
—— (E)-6-(2,3-dihydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione 1173698-49-1 C12H9N3O6
(E)-6-(2,3-dihydroxystyryl)-5-nitropyrimidine-2,4(1H,3H)-dione
—— 2-(3-chloro-4-hydroxyphenyl)-2-methyl-malonic acid 79669-16-2 C10H9ClO5
2-(3-chloro-4-hydroxyphenyl)-2-methyl-malonic acid
—— N-[2-[6-(7-fluoro-1-benzothiophen-3-yl)pyridin-2-yl]-2-oxoethyl]-4-hydroxy-3-methoxybenzamide 1569080-16-5 C23H17FN2O4S
N-[2-[6-(7-fluoro-1-benzothiophen-3-yl)pyridin-2-yl]-2-oxoethyl]-4-hydroxy-3-methoxybenzamide
—— 1-(3-Hydroxy-5-methoxyphenyl)-propan-2-on 71094-57-0 C10H12O3
1-(3-Hydroxy-5-methoxyphenyl)-propan-2-on
—— 3-hydroxy-5-methoxybenzyl-2-methyl-1,3-dioxolane 1314138-33-4 C12H16O4
3-hydroxy-5-methoxybenzyl-2-methyl-1,3-dioxolane
—— 3-(difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 1605330-08-2 C13H17BF2O3
3-(difluoromethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
—— 2,4-Dimethyl-3-hydroxyfluorbenzol 26829-79-8 C8H9FO
2,4-Dimethyl-3-hydroxyfluorbenzol
—— 4-(Methylsulfonyl)-3-nitrophenol 1187658-95-2 C7H7NO5S
4-(Methylsulfonyl)-3-nitrophenol
—— (Z)-4-(2-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 61466-12-4 C17H14N2O2
(Z)-4-(2-hydroxybenzylidene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
—— 5-cyano-2-hydroxy-N,N-dimethyl-3-nitrobenzamide 473731-56-5 C10H9N3O4
5-cyano-2-hydroxy-N,N-dimethyl-3-nitrobenzamide
—— 2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenol 414882-44-3 C13H20N2O2
2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenol
—— 2-[[(4,6-Dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-4-nitrophenol 300567-28-6 C13H13N5O3
2-[[(4,6-Dimethylpyrimidin-2-yl)hydrazinylidene]methyl]-4-nitrophenol
—— 3-(2-hydroxy-3-bromo-5-methylphenyl)-5-phenylisoxazole 29976-90-7 C16H12BrNO2
3-(2-hydroxy-3-bromo-5-methylphenyl)-5-phenylisoxazole
—— N-(4-hydroxy-3-methoxybenzylidene)-2-phenylethanamine 115372-26-4 C16H17NO2
N-(4-hydroxy-3-methoxybenzylidene)-2-phenylethanamine
—— 4-(2-Hydroxy-phenyl)-5,6-dimethyl-4,5-dihydro-2H-[1,2,4]triazin-3-one 113922-41-1 C11H13N3O2
4-(2-Hydroxy-phenyl)-5,6-dimethyl-4,5-dihydro-2H-[1,2,4]triazin-3-one
—— 4-(1,1-dihydroperfluorohexyloxy)phenol 129560-96-9 C12H7F11O2
4-(1,1-dihydroperfluorohexyloxy)phenol
—— 4-(1,1-dihydroperfluorooctyloxy)phenol 129560-97-0 C14H7F15O2
4-(1,1-dihydroperfluorooctyloxy)phenol
—— (R)-4-(6'-chloro-4'-methylhexyloxy)phenol 122160-36-5 C13H19ClO2
(R)-4-(6'-chloro-4'-methylhexyloxy)phenol
—— 2-(4-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethoxy}-phenoxy)-N-(2-methoxy-ethyl)-acetamide 139734-53-5 C22H30N2O7
2-(4-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethoxy}-phenoxy)-N-(2-methoxy-ethyl)-acetamide
—— 2-(1-(4-hydroxyphenyl)-3-(oxazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl)acetonitrile 1610369-82-8 C14H12N4O2
2-(1-(4-hydroxyphenyl)-3-(oxazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl)acetonitrile
—— 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