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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
—— 5-chloro-4-(2,5-difluoro-4-hydroxyphenyl)-3-(3,5-dimethylisoxazol-4-yl)-N'-hydroxythiophene-2-carboximidamide 1360605-02-2 C16H12ClF2N3O3S
5-chloro-4-(2,5-difluoro-4-hydroxyphenyl)-3-(3,5-dimethylisoxazol-4-yl)-N'-hydroxythiophene-2-carboximidamide
—— N-(2-(Dimethylamino)-1-methylethyl)-N-(2-thienyl)propionamide picrate 94030-34-9 C18H23N5O8S
N-(2-(Dimethylamino)-1-methylethyl)-N-(2-thienyl)propionamide picrate
—— N,N'-Bis(4-hydroxyphenyl)thioperoxydicarbamic acid 94023-58-2 C14H12N2O2S4
N,N'-Bis(4-hydroxyphenyl)thioperoxydicarbamic acid
—— Sodium 4-arsono-2-nitrophenolate 5985-41-1 C6H5AsNNaO6
Sodium 4-arsono-2-nitrophenolate
—— Mercresin 8063-34-1 C18H23ClHgO2
Mercresin
—— (-)-2-(3-Pyridyl)piperidine dipicrate 37520-45-9 C22H20N8O14
(-)-2-(3-Pyridyl)piperidine dipicrate
—— 3-Ethyl-3-(p-hydroxyphenyl)-1-methylpiperidine, hydrochloride 93760-11-3 C14H22ClNO
3-Ethyl-3-(p-hydroxyphenyl)-1-methylpiperidine, hydrochloride
—— 4,4'-(Iminobis(4,1-phenylene(1-methylethylidene)))bisphenol 85586-53-4 C30H27NO2
4,4'-(Iminobis(4,1-phenylene(1-methylethylidene)))bisphenol
—— (Methyl-1,3-phenylene)bis(iminocarbonyloxy-2,1-ethanediyloxy-4,1-phenylene(1-methylethylidene)-4,1-phenyleneoxy-2,1-ethanediyl) diacrylate 85865-95-8 C34H34N2O10
(Methyl-1,3-phenylene)bis(iminocarbonyloxy-2,1-ethanediyloxy-4,1-phenylene(1-methylethylidene)-4,1-phenyleneoxy-2,1-ethanediyl) diacrylate
—— Phenyl-2-piperidylcarbinol*HCl 32467-95-1 C12H17NO2*ClH
Phenyl-2-piperidylcarbinol*HCl
—— 1,2-Benzisothiazole-2(3H)-carboxylic acid, 3,3-bis(4-hydroxy-3,5-dimethoxyphenyl)-, 2-(methylsulfonyl)ethyl ester, 1,1-dioxide 70367-99-6 C27H29NO12S2
1,2-Benzisothiazole-2(3H)-carboxylic acid, 3,3-bis(4-hydroxy-3,5-dimethoxyphenyl)-, 2-(methylsulfonyl)ethyl ester, 1,1-dioxide
—— 1,4,5,6-Tetrahydro-5-methoxypyrimidine picrate 900-53-8 C11H13N5O8
1,4,5,6-Tetrahydro-5-methoxypyrimidine picrate
—— 3-methyl-2-[(E)-pent-3-en-2-yl]phenol 1353001-88-3 C12H16O
3-methyl-2-[(E)-pent-3-en-2-yl]phenol
—— (S)-4-(1-amino-3-hydroxypropyl)phenol 1213129-23-7 C9H13NO2
(S)-4-(1-amino-3-hydroxypropyl)phenol
—— 5-(2-hydroxy-4-methyl-3,5-dinitro-phenyl)-pyridazin-3(2H)-one 1321900-60-0 C11H8N4O6
5-(2-hydroxy-4-methyl-3,5-dinitro-phenyl)-pyridazin-3(2H)-one
—— 5-(2-hydroxy-4-methyl-3,5-dinitro-phenyl)-2-phenyl-2H-pyridazin-3-one 1321900-71-3 C17H12N4O6
5-(2-hydroxy-4-methyl-3,5-dinitro-phenyl)-2-phenyl-2H-pyridazin-3-one
—— benzyl N-[3,5,7-tris[3-[2-(3,4-dihydroxyphenyl)ethylamino]-3-oxopropyl]-1-adamantyl]carbamate 1326757-20-3 C51H62N4O11
benzyl N-[3,5,7-tris[3-[2-(3,4-dihydroxyphenyl)ethylamino]-3-oxopropyl]-1-adamantyl]carbamate
—— (2Z,4Z)-N-[(E)-3-[(1S,11S,13R)-7-hydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6,15-tetraen-11-yl]prop-1-enyl]hepta-2,4-dienamide 1350978-77-6 C25H29NO5
(2Z,4Z)-N-[(E)-3-[(1S,11S,13R)-7-hydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6,15-tetraen-11-yl]prop-1-enyl]hepta-2,4-dienamide
—— 3-[3-amino-5,7-bis[3-[2-(3,4-dihydroxyphenyl)ethylamino]-3-oxopropyl]-1-adamantyl]-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide 1326757-22-5 C43H56N4O9
3-[3-amino-5,7-bis[3-[2-(3,4-dihydroxyphenyl)ethylamino]-3-oxopropyl]-1-adamantyl]-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide
—— (1S,11S,13S,15S)-15-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-11-(2-hydroxyethyl)-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one 1350979-11-1 C23H36O6Si
(1S,11S,13S,15S)-15-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-11-(2-hydroxyethyl)-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one
—— (2Z,4Z)-N-[(E)-3-[(1S,11S,13S,15S)-15-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide 1350979-10-0 C31H45NO6Si
(2Z,4Z)-N-[(E)-3-[(1S,11S,13S,15S)-15-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide
—— (2Z,4Z)-N-[(E)-3-[(1S,11S,13R,16S)-16-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide 1350979-07-5 C31H45NO6Si
(2Z,4Z)-N-[(E)-3-[(1S,11S,13R,16S)-16-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide
—— C11-epi-apicularen A 332112-98-8 C25H31NO6
C11-epi-apicularen A
—— (1S,11S,13R)-7-hydroxy-11-(2-hydroxyethyl)-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6,15-tetraen-9-one 1350979-03-1 C17H20O5
(1S,11S,13R)-7-hydroxy-11-(2-hydroxyethyl)-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6,15-tetraen-9-one
—— (1S,11S,13R,16S)-16-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-11-(2-hydroxyethyl)-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one 1350978-97-0 C23H36O6Si
(1S,11S,13R,16S)-16-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-11-(2-hydroxyethyl)-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-9-one
—— 2-[(Z)-(4-Methyl-3-propyl-1,3-thiazol-2(3H)-ylidene)amino]phenol 148474-12-8 C13H16N2OS
2-[(Z)-(4-Methyl-3-propyl-1,3-thiazol-2(3H)-ylidene)amino]phenol
—— 4-Fluoro-2,5-dimethoxyphenol 1208078-31-2 C8H9FO3
4-Fluoro-2,5-dimethoxyphenol
—— (1E)-1-[4-(3,4-dihydroxyphenyl)-3-methyl-1,3-thiazol-2-ylidene]guanidine —— C11H12N4O2S
(1E)-1-[4-(3,4-dihydroxyphenyl)-3-methyl-1,3-thiazol-2-ylidene]guanidine
—— 3-[(E)-(3,4,5-Trimethyl-1,3-thiazol-2(3H)-ylidene)amino]phenol 66666-76-0 C12H14N2OS
3-[(E)-(3,4,5-Trimethyl-1,3-thiazol-2(3H)-ylidene)amino]phenol
—— (1E)-1-[4-(2,5-dihydroxyphenyl)-3-methyl-1,3-thiazol-2-ylidene]guanidine —— C11H12N4O2S
(1E)-1-[4-(2,5-dihydroxyphenyl)-3-methyl-1,3-thiazol-2-ylidene]guanidine
—— 2-[(Z)-(3-Ethyl-4-methyl-1,3-thiazol-2(3H)-ylidene)amino]phenol 148474-11-7 C12H14N2OS
2-[(Z)-(3-Ethyl-4-methyl-1,3-thiazol-2(3H)-ylidene)amino]phenol
—— Propanamide, N-cyclopropyl-3-(4-hydroxyphenoxy)- 1251102-82-5 C12H15NO3
Propanamide, N-cyclopropyl-3-(4-hydroxyphenoxy)-
—— 4-fluoro-3,5-dimethylphenol 1043450-63-0 C8H9FO
4-fluoro-3,5-dimethylphenol
—— 3-methoxy-4-hydroxyphenylpropenoic acid 1208246-60-9 C10H10O4
3-methoxy-4-hydroxyphenylpropenoic acid
—— 2-methyl-2-(4-hydroxyphenyl)-oxirane 1338606-45-3 C9H10O2
2-methyl-2-(4-hydroxyphenyl)-oxirane
—— 3-[(2-Bromoethyl)amino]-6-methyl-2-nitrophenol 62106-38-1 C9H11BrN2O3
3-[(2-Bromoethyl)amino]-6-methyl-2-nitrophenol
—— 4-(4-Bromothiophen-2-yl)phenol 1416018-18-2 C10H7BrOS
4-(4-Bromothiophen-2-yl)phenol
—— 2,4,6-tris[(1H-pyrazol-1-yl)methyl]benzene-1,3,5-triol 1403357-17-4 C18H18N6O3
2,4,6-tris[(1H-pyrazol-1-yl)methyl]benzene-1,3,5-triol
—— Methyl 4-(3-hydroxy-4-methoxyphenyl)butanoate 1403560-11-1 C12H16O4
Methyl 4-(3-hydroxy-4-methoxyphenyl)butanoate
—— 4-[(3-Hydroxypropyl)amino]-2-nitrophenol 177080-35-2 C9H12N2O4
4-[(3-Hydroxypropyl)amino]-2-nitrophenol
—— 1-(2-Bromo-5-hydroxyphenyl)-3-methyl-s-triazine-2,4,6-(1H,3H,5H)-trione 179028-18-3 C10H8BrN3O4
1-(2-Bromo-5-hydroxyphenyl)-3-methyl-s-triazine-2,4,6-(1H,3H,5H)-trione
—— 2-(2-chloro-5-hydroxyphenyl)acetic acid 149029-87-8 C8H7ClO3
2-(2-chloro-5-hydroxyphenyl)acetic acid
—— 4-(2-Cyclohexyl-ethyl)-phenol 1940-46-1 C14H20O
4-(2-Cyclohexyl-ethyl)-phenol
—— 4-(Dodecylsulfanyl)-2-methylphenol 114108-61-1 C19H32OS
4-(Dodecylsulfanyl)-2-methylphenol
—— 2-tert-butyl-6-cyclohexen-1-yl-4-methoxyphenol 209905-17-9 C17H24O2
2-tert-butyl-6-cyclohexen-1-yl-4-methoxyphenol
—— 4-(2-Hydroxyethoxy)-3-methylphenol 65180-39-4 C9H12O3
4-(2-Hydroxyethoxy)-3-methylphenol
—— 2-Tert-butyl-6-[[3-[(3-tert-butyl-2-hydroxy-5-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-4-methoxyphenol 1376434-72-8 C28H42N2O4
2-Tert-butyl-6-[[3-[(3-tert-butyl-2-hydroxy-5-methoxyphenyl)methyl]-1,3-diazinan-1-yl]methyl]-4-methoxyphenol
—— (E)-ethyl 5-(5-bromo-2-hydroxyphenyl)pent-2-enoate 1360054-34-7 C13H15BrO3
(E)-ethyl 5-(5-bromo-2-hydroxyphenyl)pent-2-enoate
—— 4-[Chloro(dimethyl)-lambda~4~-sulfanyl]-3-methylphenol 37596-80-8 C9H13ClOS
4-[Chloro(dimethyl)-lambda~4~-sulfanyl]-3-methylphenol
—— 391934-70-6 C15H24O4Si