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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
—— o-hydroxyphenyl isothiocyanate 86695-08-1 C7H5NOS
o-hydroxyphenyl isothiocyanate
—— acetic acid-(3-amino-4-hydroxy-5-nitro-anilide) 6527-73-7 C8H9N3O4
acetic acid-(3-amino-4-hydroxy-5-nitro-anilide)
—— 2-Methoxy-6-[(tricyclo[3.3.1.13,7]dec-1-ylamino)methyl]phenol 57304-73-1 C18H25NO2
2-Methoxy-6-[(tricyclo[3.3.1.13,7]dec-1-ylamino)methyl]phenol
—— 4-(2-Diethoxyphosphoryl-2-fluoroethyl)phenol 209120-16-1 C12H18FO4P
4-(2-Diethoxyphosphoryl-2-fluoroethyl)phenol
—— pentachlorophenol-dicyclohexylcarbodiimid complex 126369-89-9 C6HCl5O*C13H22N2
pentachlorophenol-dicyclohexylcarbodiimid complex
—— 4,6-di-tert-butyl-3-nitrobenzene-1,2-diol 101777-28-0 C14H21NO4
4,6-di-tert-butyl-3-nitrobenzene-1,2-diol
—— 3-chloro-4-hydroxy-5-methoxybenzoyl chloride 888731-74-6 C8H6Cl2O3
3-chloro-4-hydroxy-5-methoxybenzoyl chloride
—— 2-Methoxy-4-[(2-pyridin-2-yl-ethylamino)-methyl]-phenol 22540-59-6 C15H18N2O2
2-Methoxy-4-[(2-pyridin-2-yl-ethylamino)-methyl]-phenol
—— (2E,4Z)-5-chloro-5-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one 1227403-42-0 C19H16ClFO4
(2E,4Z)-5-chloro-5-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
—— 5,11,17,23-tetrakis(chlorosulphonyl)calix<4>arene-25,26,27,28-tetraol 139097-76-0 C28H20Cl4O12S4
5,11,17,23-tetrakis(chlorosulphonyl)calix<4>arene-25,26,27,28-tetraol
—— 4-propoxy-phenethyl alcohol 104174-22-3 C11H16O2
4-propoxy-phenethyl alcohol
—— (4-Ethoxycarbonylmethyl-2-hydroxy-phenyl)-hydroxy-acetic acid methyl ester 169785-11-9 C13H16O6
(4-Ethoxycarbonylmethyl-2-hydroxy-phenyl)-hydroxy-acetic acid methyl ester
—— 4-(5-phenylpentyl)phenol 57344-26-0 C17H20O
4-(5-phenylpentyl)phenol
—— 1-(1-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide 339246-36-5 C11H15N3OS
1-(1-(4-hydroxyphenyl)butan-2-ylidene)thiosemicarbazide
—— 4-(but-3'-enyloxy)-2,6-di-t-butylphenol 660410-33-3 C18H28O2
4-(but-3'-enyloxy)-2,6-di-t-butylphenol
—— acetoxymethyl 4-hydroxy-phenyl-acetate 607713-96-2 C11H12O5
acetoxymethyl 4-hydroxy-phenyl-acetate
—— hydroquinone; compound with ethylamine 38446-09-2 C2H7N*C6H6O2
hydroquinone; compound with ethylamine
—— (4R,5R)-(+)-5-ethyl-1-(4-hydroxy-3-methoxyphenethyl)-2-oxo-4-piperidineacetic acid ethyl ester 82310-90-5 C20H29NO5
(4R,5R)-(+)-5-ethyl-1-(4-hydroxy-3-methoxyphenethyl)-2-oxo-4-piperidineacetic acid ethyl ester
—— (4R,5R)-(+)-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid ethyl ester 74282-34-1 C20H29NO5
(4R,5R)-(+)-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid ethyl ester
—— (+/-)-trans-1-(3,4-dimethyloxy-2-hydroxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester —— C21H31NO6
(+/-)-trans-1-(3,4-dimethyloxy-2-hydroxyphenethyl)-3-ethyl-2-oxo-4-piperidineacetic acid ethyl ester
—— 4-isopropoxy-3-methoxyphenol 86636-03-5 C10H14O3
4-isopropoxy-3-methoxyphenol
—— 2-[(2S,4S,5R)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl] phenol 1040753-65-8 C19H23NO2
2-[(2S,4S,5R)-3-isopropyl-4-methyl-5-phenyloxazolidin-2-yl] phenol
—— 4-(3,4-dihydro-2H-pyran-2-ylmethoxy)phenol 319426-09-0 C12H14O3
4-(3,4-dihydro-2H-pyran-2-ylmethoxy)phenol
—— 2,5-dibromo-p-cresol 344249-21-4 C7H6Br2O
2,5-dibromo-p-cresol
—— 4-[2-(Ethenyloxy)ethoxy]phenol 127396-01-4 C10H12O3
4-[2-(Ethenyloxy)ethoxy]phenol
—— 13,13'-<2,5-Dihydroxy-1,4-benzenediylbis(1,4,7,10-tetraoxa-13-aza-cyclopentadecane)> 134077-83-1 C28H48N2O10
13,13'-<2,5-Dihydroxy-1,4-benzenediylbis(1,4,7,10-tetraoxa-13-aza-cyclopentadecane)>
—— 2-(3-Hydroxy-4-methoxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol 151792-74-4 C15H14O4S
2-(3-Hydroxy-4-methoxyphenyl)-2,3-dihydro-1,4-benzoxathiin-6-ol
—— 4,6-di(1,2,3-thiadiazol-4-yl)-1,3-phenylenediol 853788-25-7 C10H6N4O2S2
4,6-di(1,2,3-thiadiazol-4-yl)-1,3-phenylenediol
—— 4-(6-hydroxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)benzene-1,2-diol 1616377-37-7 C14H12O4S
4-(6-hydroxy-2,3-dihydrobenzo[1,4]oxathiin-2-yl)benzene-1,2-diol
—— 5-[6-[Tert-butyl(dimethyl)silyl]oxy-2,3-dihydro-1,4-benzoxathiin-2-yl]-2-methoxyphenol 188047-97-4 C21H28O4SSi
5-[6-[Tert-butyl(dimethyl)silyl]oxy-2,3-dihydro-1,4-benzoxathiin-2-yl]-2-methoxyphenol
—— 4-(2-((1-adamantylmethyl)amino)-1-hydroxyethyl)phenol 1050520-90-5 C19H27NO2
4-(2-((1-adamantylmethyl)amino)-1-hydroxyethyl)phenol
—— 3-adamantan-1-ylmethyl-5-(4-hydroxy-phenyl)-oxazolidin-2-one 1050520-85-8 C20H25NO3
3-adamantan-1-ylmethyl-5-(4-hydroxy-phenyl)-oxazolidin-2-one
—— 3-{4-[(dimethylamino)methyl]tetrahydro-pyran-4-yl}phenol 868849-48-3 C14H21NO2
3-{4-[(dimethylamino)methyl]tetrahydro-pyran-4-yl}phenol
—— 4,5-dihydroxyisophthalonitrile 116314-79-5 C8H4N2O2
4,5-dihydroxyisophthalonitrile
—— 2′-(2,5-dihydrophenyl)ethanol 13398-95-3 C8H10O3
2′-(2,5-dihydrophenyl)ethanol
—— [1-(2,3-dihydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 756900-99-9 C13H19NO4
[1-(2,3-dihydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester
—— [2-(4-hydroxy-phenoxy)-ethyl]-trimethyl-ammonium; bromide 112401-41-9 Br*C11H18NO2
[2-(4-hydroxy-phenoxy)-ethyl]-trimethyl-ammonium; bromide
—— Methyl 3-hydroxy-5-methylbenzenepropanoate 62358-70-7 C11H14O3
Methyl 3-hydroxy-5-methylbenzenepropanoate
—— N-(5-bromo-2-hydroxybenzylidene)pyridin-2-amine 15789-73-8 C12H9BrN2O
N-(5-bromo-2-hydroxybenzylidene)pyridin-2-amine
—— 2,5-Bis(trimethylsilyl)-hydroquinone 101907-54-4 C12H22O2Si2
2,5-Bis(trimethylsilyl)-hydroquinone
—— N'-amino-2-(3,5-ditert-butyl-4-hydroxyphenoxy)ethanimidamide 161153-40-8 C16H27N3O2
N'-amino-2-(3,5-ditert-butyl-4-hydroxyphenoxy)ethanimidamide
—— 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxyacetonitrile 137841-67-9 C16H23NO2
3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxyacetonitrile
—— 5-<<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy>methyl>-1,3,4-thiadiazole-2(3H)-thione 137841-51-1 C17H24N2O2S2
5-<<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy>methyl>-1,3,4-thiadiazole-2(3H)-thione
—— 2-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy>ethanethioamide 137841-68-0 C16H25NO2S
2-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy>ethanethioamide
—— N-butyl-1H-benzimidazol-2-amine;2,4,6-trinitrophenol 61164-68-9 C17H18N6O7
N-butyl-1H-benzimidazol-2-amine;2,4,6-trinitrophenol
—— 3-benzylideneamino-5-(2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one 17521-30-1 C17H12N2O2S2
3-benzylideneamino-5-(2-hydroxy-benzylidene)-2-thioxo-thiazolidin-4-one
—— [1-(13)C]benzene-1,2,4-triol 1032336-13-2 C6H6O3
[1-(13)C]benzene-1,2,4-triol
—— 5-Deuterio-2-methylphenol 116467-71-1 C7H8O
5-Deuterio-2-methylphenol
—— (s)-4-(2'-methylbutyloxy)phenol 95880-51-6 C11H16O2
(s)-4-(2'-methylbutyloxy)phenol
—— 4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-bis[2-(aminothioxomethyl)hydrazide] 1270020-09-1 C17H21N7O3S2
4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-bis[2-(aminothioxomethyl)hydrazide]