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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
—— Thiophosphoric acid S-(5-chloro-2-hydroxy-phenyl) ester O,O'-diethyl ester 3739-29-5 C10H14ClO4PS
Thiophosphoric acid S-(5-chloro-2-hydroxy-phenyl) ester O,O'-diethyl ester
—— N-(3-hydroxy-4-methoxyphenethyl)-2-(2-bromo-5-methoxyphenyl)acetamide 93631-31-3 C18H20BrNO4
N-(3-hydroxy-4-methoxyphenethyl)-2-(2-bromo-5-methoxyphenyl)acetamide
—— Bis-(m-hydroxyphenyl)-methyl-phosphinoxid 72835-30-4 C13H13O3P
Bis-(m-hydroxyphenyl)-methyl-phosphinoxid
—— 3,3-Dimethyl-1-aza-spiro[4.5]dec-1-ene-4-carboxylic acid ethyl ester; compound with picric acid 117103-26-1 C6H3N3O7*C14H23NO2
3,3-Dimethyl-1-aza-spiro[4.5]dec-1-ene-4-carboxylic acid ethyl ester; compound with picric acid
—— N<sup>1</sup>-(3-(2-hydroxybenzylidene-amino)propylamino)ethyl-benzylidenepropane-1,3-diamine 75086-79-2 C22H30N4O2
N<sup>1</sup>-(3-(2-hydroxybenzylidene-amino)propylamino)ethyl-benzylidenepropane-1,3-diamine
—— 2-(2-Phenyl-5-pyrazin-2-yl-3,4-dihydro-2H-pyrazol-3-yl)-phenol 75303-16-1 C19H16N4O
2-(2-Phenyl-5-pyrazin-2-yl-3,4-dihydro-2H-pyrazol-3-yl)-phenol
—— 4,5-diheptyl-1,2-dihydroxybenzene 162131-21-7 C20H34O2
4,5-diheptyl-1,2-dihydroxybenzene
—— (1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)cyclopentane-1-carboxamide 1427204-45-2 C27H28N4O5
(1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)cyclopentane-1-carboxamide
—— N-((1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)cyclopentyl)nicotinamide 1427204-53-2 C27H28N4O5
N-((1r,3R,4S)-3,4-bis((2-hydroxy-3-methoxybenzylidene)amino)cyclopentyl)nicotinamide
—— 2,6-dimethoxy-4-{2-[5-(1,1,2,2-tetramethyl-1-silapropoxy)cyclohexa-1,4-dienyl]ethyl}phenol 731849-04-0 C22H34O4Si
2,6-dimethoxy-4-{2-[5-(1,1,2,2-tetramethyl-1-silapropoxy)cyclohexa-1,4-dienyl]ethyl}phenol
—— 2-undecylbenzene-1,3,5-triol 96756-23-9 C17H28O3
2-undecylbenzene-1,3,5-triol
—— 6-<3-(benzyloxy)-1-propynyl>-2-chloro-3,4-dimethoxyphenol 108213-24-7 C18H17ClO4
6-<3-(benzyloxy)-1-propynyl>-2-chloro-3,4-dimethoxyphenol
—— 2-((2E,6E)-8-Chloro-3,7-dimethyl-octa-2,6-dienyl)-4-(tetrahydro-pyran-2-yloxy)-phenol 104210-43-7 C21H29ClO3
2-((2E,6E)-8-Chloro-3,7-dimethyl-octa-2,6-dienyl)-4-(tetrahydro-pyran-2-yloxy)-phenol
—— 2-Hydroxy-6-methoxy-3,5-dimethyl-benzonitril 90921-67-8 C10H11NO2
2-Hydroxy-6-methoxy-3,5-dimethyl-benzonitril
—— N-[(3R,7R)-(-)-jasmonoyl]dopamine 866421-55-8 C20H27NO4
N-[(3R,7R)-(-)-jasmonoyl]dopamine
—— 6-Amino-1-chlor-3-hydroxy-2-nitro-benzol 13550-75-9 C6H5ClN2O3
6-Amino-1-chlor-3-hydroxy-2-nitro-benzol
—— (2R,5S)-5-(3,4-Dimethoxy-phenyl)-2-(4-hydroxy-3-methoxy-benzyl)-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester 130097-17-5 C22H24Cl3NO7
(2R,5S)-5-(3,4-Dimethoxy-phenyl)-2-(4-hydroxy-3-methoxy-benzyl)-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester
—— 2-(2-Chloroethylthio)-3,5-dimethylphenol 36438-05-8 C10H13ClOS
2-(2-Chloroethylthio)-3,5-dimethylphenol
—— C-dec-1-enylresorcinarene 155401-88-0 C68H96O8
C-dec-1-enylresorcinarene
—— (+)-2-(2-ethylphenylamino)-3-hydroxymorphinan trifluoroacetate 1262868-13-2 C2HF3O2*C24H30N2O
(+)-2-(2-ethylphenylamino)-3-hydroxymorphinan trifluoroacetate
—— (E)-1-(2,6-dihydroxy-4-methylphenyl)but-2-en-1-one 1616807-16-9 C11H12O3
(E)-1-(2,6-dihydroxy-4-methylphenyl)but-2-en-1-one
—— 2,4-di-tert-pentyl-6-(trimethylsilyl)phenol 1334501-83-5 C19H34OSi
2,4-di-tert-pentyl-6-(trimethylsilyl)phenol
—— 6-chloro-2-(2-hydroxyphenyl)-3,3a-dihydropyrazolo[5,1-a]isoindol-8-one 1415466-11-3 C16H11ClN2O2
6-chloro-2-(2-hydroxyphenyl)-3,3a-dihydropyrazolo[5,1-a]isoindol-8-one
—— 5,11,23,29-tetra-p-tert-butylcalix[6]arene 176038-72-5 C58H68O6
5,11,23,29-tetra-p-tert-butylcalix[6]arene
—— (2Z,5Z)-5-[(2-amino(1,3-thiazol-5-yl))methylene]-2-[(4-hydroxy-2-methylphenyl)azamethylene]-1,3-thiazolidin-4-one 1253208-76-2 C14H12N4O2S2
(2Z,5Z)-5-[(2-amino(1,3-thiazol-5-yl))methylene]-2-[(4-hydroxy-2-methylphenyl)azamethylene]-1,3-thiazolidin-4-one
—— 2-Chlor-4,5-dimethylphenol (4-Methyl-<C14>) 17819-94-2 C8H9ClO
2-Chlor-4,5-dimethylphenol (4-Methyl-<C14>)
—— 5-fluoro-2-hydroxybenzaldehyde oxime 91407-40-8 C7H6FNO2
5-fluoro-2-hydroxybenzaldehyde oxime
—— (5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(3-phenyl-propionyl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one 871905-17-8 C42H53N3O8Si
(5R,6R)-5-Benzyl-2,4-bis-(4-hydroxy-3-methoxy-benzyl)-1-(3-phenyl-propionyl)-6-(2-trimethylsilanyl-ethoxymethoxy)-[1,2,4]triazepan-3-one
—— Nornicotine dipicrate 6255-01-2 C21H18N8O14
Nornicotine dipicrate
—— 4-[2,2,2-trifluoro-1-(2-hydroxy-ethylsulfanyl)-ethyl]-phenol 1279691-47-2 C10H11F3O2S
4-[2,2,2-trifluoro-1-(2-hydroxy-ethylsulfanyl)-ethyl]-phenol
—— Phenol, 4-bromo-2-fluoro-6-[1-(methylamino)ethyl]- 1824263-96-8 C9H11BrFNO
Phenol, 4-bromo-2-fluoro-6-[1-(methylamino)ethyl]-
—— 6,8-Difluoro-4-hydroxynaphthalene-2-carbonitrile 1221565-17-8 C11H5F2NO
6,8-Difluoro-4-hydroxynaphthalene-2-carbonitrile
—— (9E,12E)-Octadeca-9,12-dienoic acid 4-hydroxy-benzylamide 18318-98-4 C25H39NO2
(9E,12E)-Octadeca-9,12-dienoic acid 4-hydroxy-benzylamide
—— 6-Iod-4-nitro-2-isopropylphenol 28043-59-6 C9H10INO3
6-Iod-4-nitro-2-isopropylphenol
—— 5-(4-chloro-1-butyloxy)-2-(4-hydroxyphenyl)pyrimidine 1202058-08-9 C14H15ClN2O2
5-(4-chloro-1-butyloxy)-2-(4-hydroxyphenyl)pyrimidine
—— N-[(Z)-(3,4-dideuterio-5-nitrofuran-2-yl)methylideneamino]-2-hydroxy-3,5-dinitro(15N)benzamide 1246833-64-6 C12H7N5O9
N-[(Z)-(3,4-dideuterio-5-nitrofuran-2-yl)methylideneamino]-2-hydroxy-3,5-dinitro(15N)benzamide
—— 1350814-95-7 C13H12O2Se
—— 3-(1H-Benzoimidazol-2-ylamino)-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one 136713-04-7 C24H19N5O3
3-(1H-Benzoimidazol-2-ylamino)-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one
—— 3,4-Dihydroxybenzamidiniumchlorid 15723-89-4 C7H8N2O2*ClH
3,4-Dihydroxybenzamidiniumchlorid
—— tris[2-(5-nitrosalicylideneamino)ethyl]amine 70292-83-0 C27H27N7O9
tris[2-(5-nitrosalicylideneamino)ethyl]amine
—— 2-(2-Nitro-phenylamino)-benzene-1,3,5-triol 97031-08-8 C12H10N2O5
2-(2-Nitro-phenylamino)-benzene-1,3,5-triol
—— 3-(2-Phenyl-5-pyrazin-2-yl-3,4-dihydro-2H-pyrazol-3-yl)-phenol 75303-17-2 C19H16N4O
3-(2-Phenyl-5-pyrazin-2-yl-3,4-dihydro-2H-pyrazol-3-yl)-phenol
—— N-[3-(tert-butoxycarbonylamino)propyl]-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276702-63-7 C14H20ClN3O7S
N-[3-(tert-butoxycarbonylamino)propyl]-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— 4-hydroxy-N-phenylbenzothioamide 4270-58-0 C13H11NOS
4-hydroxy-N-phenylbenzothioamide
—— 3-Methyl-4-(cyclopenten-2-yl)-phenol 92722-76-4 C12H14O
3-Methyl-4-(cyclopenten-2-yl)-phenol
—— (Z)-2,5-dihydroxy-6-(4-oxobut-2-enyl)-benzonitrile 130663-63-7 C11H9NO3
(Z)-2,5-dihydroxy-6-(4-oxobut-2-enyl)-benzonitrile
—— 4-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol 1332498-21-1 C13H14N2O3
4-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-benzene-1,2-diol
—— 1-[2-(2-bromoethoxy)ethyl]-4-methoxybenzene 1046818-63-6 C11H15BrO2
1-[2-(2-bromoethoxy)ethyl]-4-methoxybenzene
—— β-(2-Hydroxy-5-brom-phenyl)-propionsaeure-ethylester 20921-12-4 C11H13BrO3
β-(2-Hydroxy-5-brom-phenyl)-propionsaeure-ethylester
—— triethylamine salt of 2-chloro-3-hydroxy-4-methoxy-6-aminophenylacetic acid 137835-97-3 C6H15N*C9H10ClNO4
triethylamine salt of 2-chloro-3-hydroxy-4-methoxy-6-aminophenylacetic acid