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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
—— methyl 2-((5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-yl)thio)acetate —— C11H10N2O5S
methyl 2-((5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-yl)thio)acetate
—— 4-(2-amino-1,3-thiazol-4-yl)-2-methoxyphenol —— C10H10N2O2S
4-(2-amino-1,3-thiazol-4-yl)-2-methoxyphenol
—— (3-hydroxy-4-cyanophenyl)methoxymethylene tricyclo[7.3.1.0(2,7)]tridec-2,7-ene —— C21H25ClO2
(3-hydroxy-4-cyanophenyl)methoxymethylene tricyclo[7.3.1.0(2,7)]tridec-2,7-ene
—— 4-(4-hydroxyphenyl)-2,6-diphenylpyrylium tetrafluoroborate —— BF4*C23H17O2
4-(4-hydroxyphenyl)-2,6-diphenylpyrylium tetrafluoroborate
—— 5-Bromo-N-salicyliden-2,3-diamino-cis-2-butenedinitrile —— C11H7BrN4O
5-Bromo-N-salicyliden-2,3-diamino-cis-2-butenedinitrile
—— (4SR,5SR)-4-acetyl-5-(2-hydroxyphenyl)-2-methylcyclopent-1-enecarboxylic acid —— C15H16O4
(4SR,5SR)-4-acetyl-5-(2-hydroxyphenyl)-2-methylcyclopent-1-enecarboxylic acid
—— (4SR,5SR)-methyl 4-acetyl-5-(2-hydroxyphenyl)-2-methylcyclopent-1-enecarboxylate —— C16H18O4
(4SR,5SR)-methyl 4-acetyl-5-(2-hydroxyphenyl)-2-methylcyclopent-1-enecarboxylate
—— 2-(N,N-diethylamino)carbonyloxymethyl-1,4-di(4-hydroxy-3,5-dimethoxybenzoyl)piperazine —— C28H37N3O10
2-(N,N-diethylamino)carbonyloxymethyl-1,4-di(4-hydroxy-3,5-dimethoxybenzoyl)piperazine
—— 4-(4-hydroxytetrahydrothiopyran-4-yl)benzene-1,3-diol —— C11H14O3S
4-(4-hydroxytetrahydrothiopyran-4-yl)benzene-1,3-diol
—— (2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[2-(hydroxyimino)-3-(3-hydroxyphenyl)propanamide] —— C22H26N4O6S2
(2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[2-(hydroxyimino)-3-(3-hydroxyphenyl)propanamide]
—— (2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(4-hydroxy-3-iodophenyl)-2-(hydroxyimino)propanamide] —— C22H24I2N4O6S2
(2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(4-hydroxy-3-iodophenyl)-2-(hydroxyimino)propanamide]
—— (2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide] —— C22H24Cl2N4O6S2
(2E,2'E)-N,N'-[2,2'-disulfanediylbis(ethane-2,1-diyl)]bis[3-(3-chloro-4-hydroxyphenyl)-2-(hydroxyimino)propanamide]
—— 7-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-N6-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide —— C22H23N5O5
7-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-7-methyl-N6-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide
—— <i>N</i>-(3-hydroxy-benzylidene)-propionamide —— C10H11NO2
<i>N</i>-(3-hydroxy-benzylidene)-propionamide
—— N’-(5-chloro-2-hydroxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide —— C15H13ClN2O4
N’-(5-chloro-2-hydroxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide
—— (Z)-3-benzyl-5-(3-chloro-4-hydroxybenzylidene)-4-isopropylfuran-2(5H)-one —— C21H19ClO3
(Z)-3-benzyl-5-(3-chloro-4-hydroxybenzylidene)-4-isopropylfuran-2(5H)-one
—— 2-Acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentanone —— C14H16O5
2-Acetyl-2-(3,4-dihydroxy-5-methoxyphenyl)cyclopentanone
—— (-)-(7R,8R)-syringylglycerol 2174104-98-2 C11H16O6
(-)-(7R,8R)-syringylglycerol
—— gnaphaffine A —— C25H24O11
gnaphaffine A
—— 3-chloro-4-(phenylseleno)phenol —— C12H9ClOSe
3-chloro-4-(phenylseleno)phenol
—— 3-chloro-6-(phenylseleno)phenol —— C12H9ClOSe
3-chloro-6-(phenylseleno)phenol
—— 5-chloro-2-(triethylsilylethynyl)phenol —— C14H19ClOSi
5-chloro-2-(triethylsilylethynyl)phenol
—— 3-chlorophenyl N-(5-nitro-2-hydroxybenzyl)carbamate —— C15H13ClN2O5
3-chlorophenyl N-(5-nitro-2-hydroxybenzyl)carbamate
—— [rac]-3-(3,5-difluoro-4-hydroxy-phenyl)-2-ethoxy-propionic acid ethyl ester —— C13H16F2O4
[rac]-3-(3,5-difluoro-4-hydroxy-phenyl)-2-ethoxy-propionic acid ethyl ester
—— 3-phenyl-5-(2'-hydroxy-5'-chlorophenyl)-Δ<sup>2</sup>-pyrazoline —— C15H13ClN2O
3-phenyl-5-(2'-hydroxy-5'-chlorophenyl)-Δ<sup>2</sup>-pyrazoline
—— 2-bromo-1-(5-(5-chloro-2-hydroxy-phenyl)-3-(4-methyl-phenyl)-4,5-dihydro-pyrazol-1-yl)-ethanone —— C18H16BrClN2O2
2-bromo-1-(5-(5-chloro-2-hydroxy-phenyl)-3-(4-methyl-phenyl)-4,5-dihydro-pyrazol-1-yl)-ethanone
—— 4-(4-(hydroxymethyl)-4,5-dihydrooxazol-2-yl)phenol —— C10H11NO3
4-(4-(hydroxymethyl)-4,5-dihydrooxazol-2-yl)phenol
—— sodium hydroxy(4-hydroxyphenyl)methanesulfonate —— C7H7O5S*Na
sodium hydroxy(4-hydroxyphenyl)methanesulfonate
—— 5-ethyl-2-iodophenol —— C8H9IO
5-ethyl-2-iodophenol
—— (E)-N'-(4-(methoxy)-2-hydroxysalicylidine)benzohydrazide —— C15H14N2O3
(E)-N'-(4-(methoxy)-2-hydroxysalicylidine)benzohydrazide
—— 4-amino-3-hydroxy-2,6-dinitro-benzonitrile —— C7H4N4O5
4-amino-3-hydroxy-2,6-dinitro-benzonitrile
—— <i>N</i>-(2-hydroxy-3,5-dinitro-phenyl)-phthalimide —— C14H7N3O7
<i>N</i>-(2-hydroxy-3,5-dinitro-phenyl)-phthalimide
—— chloro-acetic acid-(2-hydroxy-3,5-dinitro-anilide) —— C8H6ClN3O6
chloro-acetic acid-(2-hydroxy-3,5-dinitro-anilide)
—— N-[2-(3,4-dihydroxyphenyl)ethyl]urea —— C9H12N2O3
N-[2-(3,4-dihydroxyphenyl)ethyl]urea
—— N-(2-hydroxyphenyl)pyridinium perchlorate —— C11H10NO*ClO4
N-(2-hydroxyphenyl)pyridinium perchlorate
—— N-(4-hydroxyphenyl)pyridinium perchlorate —— C11H10NO*ClO4
N-(4-hydroxyphenyl)pyridinium perchlorate
—— (2-hydroxyphenyl)thiophen-2-ylmethanol —— C11H10O2S
(2-hydroxyphenyl)thiophen-2-ylmethanol
—— 5-(ethylamino)-4-methyl-2-nitrosophenol hydrochloride —— C9H12N2O2*ClH
5-(ethylamino)-4-methyl-2-nitrosophenol hydrochloride
—— 4-(5-(benzylthio)-1,3,4-oxadiazol-2-yl)benzene-1,2-diol —— C15H12N2O3S
4-(5-(benzylthio)-1,3,4-oxadiazol-2-yl)benzene-1,2-diol
—— 9,10-methylene rivanil —— C27H45NO4
9,10-methylene rivanil
—— 3-bromo-4,5-dihydroxybenzonitrile 38897-25-5 C7H4BrNO2
3-bromo-4,5-dihydroxybenzonitrile
—— 2-hydroxyphenyl-hept-2-ynyl sulfide —— C26H30O2S
2-hydroxyphenyl-hept-2-ynyl sulfide
—— 2-(4-hydroxy-phenyl)-acetimidic acid ethyl ester —— C10H13NO2
2-(4-hydroxy-phenyl)-acetimidic acid ethyl ester
—— 4-hydroxybenzenethioacetamide —— C8H9NOS
4-hydroxybenzenethioacetamide
—— 2-(1-hydroxycyclobutyl)phenol —— C10H12O2
2-(1-hydroxycyclobutyl)phenol
—— N-(cyanomethyl)-2-hydroxy-N-methyl-5-nitrobenzamide —— C10H9N3O4
N-(cyanomethyl)-2-hydroxy-N-methyl-5-nitrobenzamide
—— N-(cyanomethyl)-2-hydroxy-5-nitrobenzamide —— C9H7N3O4
N-(cyanomethyl)-2-hydroxy-5-nitrobenzamide
—— N-(1-cyanocyclopropyl)-2-hydroxy-5-nitrobenzamide —— C11H9N3O4
N-(1-cyanocyclopropyl)-2-hydroxy-5-nitrobenzamide
—— N-benzyl-N-(cyanomethyl)-2-hydroxy-5-nitrobenzamide —— C16H13N3O4
N-benzyl-N-(cyanomethyl)-2-hydroxy-5-nitrobenzamide
—— (Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(1H-indol-3-yl)-acrylonitrile —— C19H16N2O3
(Z)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(1H-indol-3-yl)-acrylonitrile