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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
—— m-Hydroxy-acetophenon-hydrazon 5757-78-8 C8H10N2O
m-Hydroxy-acetophenon-hydrazon
—— 2,3,9,10-Tetrahydroxy-6,7-dihydro-5H-dibenzo<a,c>cyclohepten 17425-65-9 C15H14O4
2,3,9,10-Tetrahydroxy-6,7-dihydro-5H-dibenzo<a,c>cyclohepten
—— 4-[(3-hydroxy-phenyl)-thioacetyl]-morpholine 500284-27-5 C12H15NO2S
4-[(3-hydroxy-phenyl)-thioacetyl]-morpholine
—— 25,26,27-trihydroxy-28-calix[4]monoquinone-17-ethylene ketal 386223-92-3 C30H26O6
25,26,27-trihydroxy-28-calix[4]monoquinone-17-ethylene ketal
—— 4,5-dihydroxy-2-methoxy-benzaldehyde 5689-99-6 C8H8O4
4,5-dihydroxy-2-methoxy-benzaldehyde
—— 4.5-Dihydroxy-2-methoxy-1-aminoaethyl-benzol 14901-09-8 C9H13NO3
4.5-Dihydroxy-2-methoxy-1-aminoaethyl-benzol
—— 2-fluoro-4-[5-(3-fluoro-5-hydroxyphenyl)thien-2-yl]phenol 1193524-97-8 C16H10F2O2S
2-fluoro-4-[5-(3-fluoro-5-hydroxyphenyl)thien-2-yl]phenol
—— 5-Methoxy-2-(tetrahydro-pyran-2-yl)-phenol 120649-45-8 C12H16O3
5-Methoxy-2-(tetrahydro-pyran-2-yl)-phenol
—— 3-(5-Dodecyloxy-2-hydroxy-benzyl)-1-methyl-1H-pyridin-2-one 672939-87-6 C25H37NO3
3-(5-Dodecyloxy-2-hydroxy-benzyl)-1-methyl-1H-pyridin-2-one
—— 3-Methoxy-2,4,5-trimethylphenol 34883-04-0 C10H14O2
3-Methoxy-2,4,5-trimethylphenol
—— 2-4-(diethylamino-2-hydroxybenzylideneamino)-5-nitrophenol 415687-15-9 C17H19N3O4
2-4-(diethylamino-2-hydroxybenzylideneamino)-5-nitrophenol
—— 3-(2-hydroxy-4,6-dimethoxyphenyl)-6-phenylcyclohex-2-en-1-one 89059-56-3 C20H20O4
3-(2-hydroxy-4,6-dimethoxyphenyl)-6-phenylcyclohex-2-en-1-one
—— 6-acetyl-3-(2-hydroxy-4-methoxyphenyl)-5-phenyl-cyclohex-2-en-1one 89059-51-8 C21H20O4
6-acetyl-3-(2-hydroxy-4-methoxyphenyl)-5-phenyl-cyclohex-2-en-1one
—— 6-(2-Hydroxy-4-methoxy-phenyl)-4-phenyl-2,3a,4,5-tetrahydro-indazol-3-one 101986-20-3 C20H18N2O3
6-(2-Hydroxy-4-methoxy-phenyl)-4-phenyl-2,3a,4,5-tetrahydro-indazol-3-one
—— 3-(2-hydroxy-4-methoxyphenyl)-5-phenylcyclohex-2-en-1-one 89059-49-4 C19H18O3
3-(2-hydroxy-4-methoxyphenyl)-5-phenylcyclohex-2-en-1-one
—— 2,6-di-<i>tert</i>-butyl-4-oxiranylmethoxy-phenol 7020-08-8 C17H26O3
2,6-di-<i>tert</i>-butyl-4-oxiranylmethoxy-phenol
—— 3,5-dimethoxy-4-(((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)phenol 1415456-03-9 C18H26O4
3,5-dimethoxy-4-(((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl)phenol
—— 2-methyl-4-hydroxy-anilino-2-imidazoline hydrochloride 95668-59-0 C10H13N3O*ClH
2-methyl-4-hydroxy-anilino-2-imidazoline hydrochloride
—— 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfone 40654-56-6 C12H6Cl2N2O8S
5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfone
—— (RS)-N-(4-cyano-benzyl)-2-(3-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide 1055905-12-8 C18H18N2O4
(RS)-N-(4-cyano-benzyl)-2-(3-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide
—— 2-ethyl-6-methyl-hydroquinone 72693-14-2 C9H12O2
2-ethyl-6-methyl-hydroquinone
—— 5-(O-ethylthiocarboxy)-3-hydroxy-4-methoxybenzaldehyde 80547-70-2 C11H12O4S2
5-(O-ethylthiocarboxy)-3-hydroxy-4-methoxybenzaldehyde
—— 2-fluoro-4-hydroxybenzothioamide 1174738-05-6 C7H6FNOS
2-fluoro-4-hydroxybenzothioamide
—— 3-fluoro-4-(methylsulfonylmethyl)phenol 1037776-17-2 C8H9FO3S
3-fluoro-4-(methylsulfonylmethyl)phenol
—— methyl 3-(4-fluoro-2-hydroxyphenyl)propanoate 936327-90-1 C10H11FO3
methyl 3-(4-fluoro-2-hydroxyphenyl)propanoate
—— 2,2-dimethyl-propionic acid 4-{2-[2-chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-ethyl}-phenyl ester 890042-59-8 C23H25ClN2O4
2,2-dimethyl-propionic acid 4-{2-[2-chloro-4-(6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenoxy]-ethyl}-phenyl ester
—— 5-(3-chloro-4-hydroxyphenyl)-3-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 617688-89-8 C18H13ClO3S
5-(3-chloro-4-hydroxyphenyl)-3-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde
—— 3-(5-Hydroxy-2-methylphenyl)-5-(4-hydroxyphenyl)-4-methyl-2-thiophenecarbaldehyde 617688-80-9 C19H16O3S
3-(5-Hydroxy-2-methylphenyl)-5-(4-hydroxyphenyl)-4-methyl-2-thiophenecarbaldehyde
—— 2-chloro-3,5-dimethoxy-4-methylphenol 39024-70-9 C9H11ClO3
2-chloro-3,5-dimethoxy-4-methylphenol
—— 2,1-benzisoxazol-7-ol 1001434-71-4 C7H5NO2
2,1-benzisoxazol-7-ol
—— 3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde 617688-83-2 C18H13ClO3S
3-(3-chloro-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-4-methylthiophene-2-carbaldehyde
—— 2,3-(3-hydroxyocta-1,7-diyne-1,8-diyl)-5,6-dimethylhydroquinone 144182-11-6 C16H16O3
2,3-(3-hydroxyocta-1,7-diyne-1,8-diyl)-5,6-dimethylhydroquinone
—— 2-bromo-6-(tert-butyldimethylsilyl)-4-methylphenol 154345-35-4 C13H21BrOSi
2-bromo-6-(tert-butyldimethylsilyl)-4-methylphenol
—— 2-fluoro-4-[5-(3-hydroxyphenyl)-3-thienyl]phenol 1193525-06-2 C16H11FO2S
2-fluoro-4-[5-(3-hydroxyphenyl)-3-thienyl]phenol
—— Formaldehyde;naphthalene-2,7-diol;phenol 26936-19-6 C17H16O4
Formaldehyde;naphthalene-2,7-diol;phenol
—— 2-Fluoro-4-[5-(3-hydroxyphenyl)-2-thienyl]phenol 1122660-29-0 C16H11FO2S
2-Fluoro-4-[5-(3-hydroxyphenyl)-2-thienyl]phenol
—— 2-(3-hydroxyphenyl)-2-isopropoxy-1,1-diisopropylethene 172024-41-8 C17H26O2
2-(3-hydroxyphenyl)-2-isopropoxy-1,1-diisopropylethene
—— benzyl 3-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylpropionate 1030600-31-7 C26H35NO7
benzyl 3-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylpropionate
—— benzyl 4-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylbutyrate 1030600-34-0 C27H37NO7
benzyl 4-[tert-butoxycarbonyl(2-hydroxy-3-isopropoxy-4-methoxybenzyl)amino]-3-phenylbutyrate
—— 2-{3-bromo-5-(trimethylsilyl)-4-[(trimethylsilyl)oxy]phenyl}ethyl methanesulfonate 1127943-39-8 C15H27BrO4SSi2
2-{3-bromo-5-(trimethylsilyl)-4-[(trimethylsilyl)oxy]phenyl}ethyl methanesulfonate
—— (3-bromo-2-[(trimethylsilyl)oxy]-5-{2-[(trimethylsilyl)oxy]ethyl}phenyl)(trimethyl)silane 1127943-34-3 C17H33BrO2Si3
(3-bromo-2-[(trimethylsilyl)oxy]-5-{2-[(trimethylsilyl)oxy]ethyl}phenyl)(trimethyl)silane
—— (6'R)-4-hydroxy-3-methoxy-5-(3',7'-dimethyl-6',7'-epoxy-2'-octenyl)benzyl alcohol 844868-76-4 C18H26O4
(6'R)-4-hydroxy-3-methoxy-5-(3',7'-dimethyl-6',7'-epoxy-2'-octenyl)benzyl alcohol
—— 4-chloro-2-fluoro-6-nitrophenol 58348-99-5 C6H3ClFNO3
4-chloro-2-fluoro-6-nitrophenol
—— 2-(2-hydroxy-3-nitrophenyl)-N-(trifluoroacetyl)ethylamine 108773-05-3 C10H9F3N2O4
2-(2-hydroxy-3-nitrophenyl)-N-(trifluoroacetyl)ethylamine
—— N-[1-(4-hydroxy-3-fluoro-phenyl)-ethyl]-acetamide 1443670-63-0 C10H12FNO2
N-[1-(4-hydroxy-3-fluoro-phenyl)-ethyl]-acetamide
—— 2-(3-methylenepentyl)phenol 51082-22-5 C12H16O
2-(3-methylenepentyl)phenol
—— 2-(2-Hydroxy-5-chlor-phenyl)-thiazolidin 78760-47-1 C9H10ClNOS
2-(2-Hydroxy-5-chlor-phenyl)-thiazolidin
—— 3,4-diiodo-phenol 1243476-86-9 C6H4I2O
3,4-diiodo-phenol
—— 2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole 1300713-17-0 C15H12N4O4S
2-(3-methoxy-4-hydroxyphenyl)-5-(4-nitrophenylamino)-1,3,4-thiadiazole
—— Ethanol, 2-(1-benzimidazolylmethoxy)-, picrate 34703-78-1 C16H15N5O9
Ethanol, 2-(1-benzimidazolylmethoxy)-, picrate