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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
—— belamcandol A 137786-93-7 C23H38O3
belamcandol A
—— N,N'-(1,4-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide) 1146684-91-4 C46H40N6O10S2
N,N'-(1,4-phenylene)bis(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)acetamide)
—— (3Z)-5-Ethyl-3-[(2-hydroxyphenyl)methylidene]thiophen-2(3H)-one 60466-76-4 C13H12O2S
(3Z)-5-Ethyl-3-[(2-hydroxyphenyl)methylidene]thiophen-2(3H)-one
—— rubrolide N 287965-29-1 C17H9Br2ClO4
rubrolide N
—— 5-Ethyl-3-[1-(2-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-3H-thiophen-2-one 60466-78-6 C14H14O3S
5-Ethyl-3-[1-(2-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-3H-thiophen-2-one
—— (3Z)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-ethylthiophen-2-one 60466-77-5 C13H11ClO2S
(3Z)-3-[(5-chloro-2-hydroxyphenyl)methylidene]-5-ethylthiophen-2-one
—— 5-fluoro-2-methoxy-4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenol 918524-34-2 C24H33FN2O2Si
5-fluoro-2-methoxy-4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)-phenol
—— (S,S,S)-2-[(3,5-bis{[4-(3-hydroxyphenyl)-4,5-dihydrooxazol-2-yl]methyl}-2,4,6-triethyl)phenyl]methyl-4-(3-hydroxyphenyl)-4,5-dihydrooxazole 873783-15-4 C42H45N3O6
(S,S,S)-2-[(3,5-bis{[4-(3-hydroxyphenyl)-4,5-dihydrooxazol-2-yl]methyl}-2,4,6-triethyl)phenyl]methyl-4-(3-hydroxyphenyl)-4,5-dihydrooxazole
—— 3-(8-Pentadecenyl)-1,2-benzenediol 2764-91-2 C21H34O2
3-(8-Pentadecenyl)-1,2-benzenediol
—— 5-bromo-4-(1,3-dioxolan-2-yl)-2-methoxyphenol 472955-00-3 C10H11BrO4
5-bromo-4-(1,3-dioxolan-2-yl)-2-methoxyphenol
—— 4-fluoro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide 329053-69-2 C15H13FN2O3
4-fluoro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide
—— (5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(5-methyl-3-oxopyrazolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181082-16-5 C14H12FN3O3S
(5Z)-5-[(4-fluoro-2-hydroxyphenyl)methylidene]-2-(5-methyl-3-oxopyrazolidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 2-(2-ethynyl-4,5-dimethoxyphenyl)ethanol 1239085-76-7 C12H14O3
2-(2-ethynyl-4,5-dimethoxyphenyl)ethanol
—— 4-(4-hydroxyphenyl)-2-methyl-2-trimethylsiloxybutane 958640-41-0 C14H24O2Si
4-(4-hydroxyphenyl)-2-methyl-2-trimethylsiloxybutane
—— 3-allyl-6-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde 479633-80-2 C12H13BrO3
3-allyl-6-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde
—— methyl 2-hydroxy-3,4-dimethoxyphenylacetate 369386-09-4 C11H14O5
methyl 2-hydroxy-3,4-dimethoxyphenylacetate
—— 4-(4-hydroxyphenyl)butan-2-aminium chloride 74432-61-4 C10H15NO*ClH
4-(4-hydroxyphenyl)butan-2-aminium chloride
—— 4-(3-amino-3-methylbutyl)phenol 83987-81-9 C11H17NO
4-(3-amino-3-methylbutyl)phenol
—— 1-({1-[3-(4-hydroxyphenyl)-1-methylpropyl]piperidin-4-yl}methyl)piperidin-4-ol 627052-30-6 C21H34N2O2
1-({1-[3-(4-hydroxyphenyl)-1-methylpropyl]piperidin-4-yl}methyl)piperidin-4-ol
—— 1,3-Benzenediol, 4-nitro-, sodium salt 63512-41-4 C6H4NNaO4
1,3-Benzenediol, 4-nitro-, sodium salt
—— 2-methoxy-4(3-methylbut-2-enoyl)phenol 98910-59-9 C12H14O3
2-methoxy-4(3-methylbut-2-enoyl)phenol
—— 3-((3,4-Dihydroxy-5-nitrophenyl)methyl)-2,5-pentanedione 132759-68-3 C12H13NO6
3-((3,4-Dihydroxy-5-nitrophenyl)methyl)-2,5-pentanedione
—— tert-butyl N-[2-(3-bromo-4-hydroxyphenyl)ethyl]carbamate 124840-72-8 C13H18BrNO3
tert-butyl N-[2-(3-bromo-4-hydroxyphenyl)ethyl]carbamate
—— (E)-4-(4-hydroxyphenyl)butan-2-one oxime 58484-75-6 C10H13NO2
(E)-4-(4-hydroxyphenyl)butan-2-one oxime
—— N-(tert-butoxycarbonyl)-3-chloro-4-hydroxyphenethylamine 676497-72-6 C13H18ClNO3
N-(tert-butoxycarbonyl)-3-chloro-4-hydroxyphenethylamine
—— 6-(2'-hydroxy)ethyl-2-methyl-4-methoxyphenol 359844-41-0 C10H14O3
6-(2'-hydroxy)ethyl-2-methyl-4-methoxyphenol
—— N',N''-bis<2-(4-hydroxyphenyl)ethyl>imidodisulfamide 82173-93-1 C16H21N3O6S2
N',N''-bis<2-(4-hydroxyphenyl)ethyl>imidodisulfamide
—— 6-methyl-2-(tetrahydro-2H-pyran-2-yl)phenol 117658-43-2 C12H16O2
6-methyl-2-(tetrahydro-2H-pyran-2-yl)phenol
—— ethyl 2-(2-hydroxyphenyl)propionate 63500-12-9 C11H14O3
ethyl 2-(2-hydroxyphenyl)propionate
—— 2-methyl-4-methoxy-6-(2-propenyl)phenol 359844-29-4 C11H14O2
2-methyl-4-methoxy-6-(2-propenyl)phenol
—— 2-nitro-4-(trifluoromethylthio)phenol 933673-33-7 C7H4F3NO3S
2-nitro-4-(trifluoromethylthio)phenol
—— N-(3-hydroxy-4-methoxyphenethyl)-1-(4-bromo-2,6-dimethylphenoxy)propan-2-amine 1268936-94-2 C20H26BrNO3
N-(3-hydroxy-4-methoxyphenethyl)-1-(4-bromo-2,6-dimethylphenoxy)propan-2-amine
—— N-(3-hydroxy-4-methoxyphenethyl)-1-(4-bromo-2,6-dimethylphenoxy)propan-2-amine hydrochloride 1268820-01-4 C20H26BrNO3*ClH
N-(3-hydroxy-4-methoxyphenethyl)-1-(4-bromo-2,6-dimethylphenoxy)propan-2-amine hydrochloride
—— N-(3-hydroxy-4-methoxyphenethyl)-1-(4-cyano-2,6-dimethylphenoxy)propan-2-amine hydrochloride 1268819-97-1 C21H26N2O3*ClH
N-(3-hydroxy-4-methoxyphenethyl)-1-(4-cyano-2,6-dimethylphenoxy)propan-2-amine hydrochloride
—— 4-(2,3-dihydro-5-hydroxy-8-methoxy-6-methylbenzo[b][1,4]oxathiin-2-yl)benzene-1,2-diol 1352754-70-1 C16H16O5S
4-(2,3-dihydro-5-hydroxy-8-methoxy-6-methylbenzo[b][1,4]oxathiin-2-yl)benzene-1,2-diol
—— 4-methoxy-2-methyl-5-(methylthio)phenol 127087-17-6 C9H12O2S
4-methoxy-2-methyl-5-(methylthio)phenol
—— 4-methoxy-2-methyl-3-(methylthio)phenol 127087-18-7 C9H12O2S
4-methoxy-2-methyl-3-(methylthio)phenol
—— 2-Methyl-6-n-hexadecyl-hydrochinon 115143-64-1 C23H40O2
2-Methyl-6-n-hexadecyl-hydrochinon
—— 4-Methyl-3-nitrobenzene-1,2-diol 92538-95-9 C7H7NO4
4-Methyl-3-nitrobenzene-1,2-diol
—— Benzenemethanol, 6-amino-3-hydroxy-2-nitro- 98451-50-4 C7H8N2O4
Benzenemethanol, 6-amino-3-hydroxy-2-nitro-
—— 2-Acetamino-4-nitro-6-sek-butylphenol 33213-29-5 C12H16N2O4
2-Acetamino-4-nitro-6-sek-butylphenol
—— (5S)-1-[(1S)-1-(2-hydroxyphenyl)ethyl]-5-prop-2-enylpyrrolidin-2-one 261172-32-1 C15H19NO2
(5S)-1-[(1S)-1-(2-hydroxyphenyl)ethyl]-5-prop-2-enylpyrrolidin-2-one
—— 4-Methyl-3-(2.2-dichlor-vinyl)-phenol 90348-56-4 C9H8Cl2O
4-Methyl-3-(2.2-dichlor-vinyl)-phenol
—— 4-Methyl-3-(2.2.2-trichlor-isopropyl)-phenol 90920-21-1 C10H11Cl3O
4-Methyl-3-(2.2.2-trichlor-isopropyl)-phenol
—— 4-methyl-3-(2,2,2-trichloroethyl)phenol 42203-95-2 C9H9Cl3O
4-methyl-3-(2,2,2-trichloroethyl)phenol
—— 3,5-Dimethyl-2,4,6-tris-hydroxymethyl-phenol 22002-39-7 C11H16O4
3,5-Dimethyl-2,4,6-tris-hydroxymethyl-phenol
—— (+/-)-(1S*,2S*,5R*,6S*)-2-(2,6-Dimethoxyphenoxy)-1-hydroxy-6-(5-hydroxy-2-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane 142677-34-7 C21H24O8
(+/-)-(1S*,2S*,5R*,6S*)-2-(2,6-Dimethoxyphenoxy)-1-hydroxy-6-(5-hydroxy-2-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane
—— 2,4-Bis-hydroxymethyl-5-methyl-phenol 64032-91-3 C9H12O3
2,4-Bis-hydroxymethyl-5-methyl-phenol
—— (E)-1-[2-hydroxy-5-(2-methylpropoxy)phenyl]-3-(5-methylthiophen-2-yl)prop-2-en-1-one 1067559-92-5 C18H20O3S
(E)-1-[2-hydroxy-5-(2-methylpropoxy)phenyl]-3-(5-methylthiophen-2-yl)prop-2-en-1-one
—— N-t-butoxycarbonyl-2-(2-iodo-4,5-dihydroxyphenyl)ethanamine 1607804-24-9 C13H18INO4
N-t-butoxycarbonyl-2-(2-iodo-4,5-dihydroxyphenyl)ethanamine