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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
—— (5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methylphenyl)-1,3-diazinane-2,4,6-trione 5974-41-4 C19H15ClN2O5
(5Z)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1-(3-methylphenyl)-1,3-diazinane-2,4,6-trione
—— (5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-(3,4-dimethylphenyl)-6-hydroxypyrimidine-2,4(3H,5H)-dione 6019-75-6 C20H17ClN2O5
(5E)-5-(3-chloro-4-hydroxy-5-methoxybenzylidene)-3-(3,4-dimethylphenyl)-6-hydroxypyrimidine-2,4(3H,5H)-dione
—— N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)acetohydrazide —— C13H14N4O3
N'-[(E)-(3-hydroxyphenyl)methylidene]-2-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)acetohydrazide
—— 2,3-dimethyl-4-thiocyanatophenol 6186-84-1 C9H9NOS
2,3-dimethyl-4-thiocyanatophenol
—— (5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 5960-00-9 C18H12FIN2O5
(5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-iodo-5-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
—— 2-Hydroxy-4-nitrobenzenesulfonamide 1261863-13-1 C6H6N2O5S
2-Hydroxy-4-nitrobenzenesulfonamide
—— 2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine 118797-50-5 C14H23NO2
2-[4-(2-ethoxyethyl)-2,3-dimethylphenoxy]ethylamine
—— 2,3-dimethyl-4-nitro-6-(2-propenyl)phenol 182010-87-3 C11H13NO3
2,3-dimethyl-4-nitro-6-(2-propenyl)phenol
—— 4-bromo-2,3-dimethyl-6-(2-propenyl)phenol 182010-84-0 C11H13BrO
4-bromo-2,3-dimethyl-6-(2-propenyl)phenol
—— 4-(2-hydroxy-3,4-dimethyl-phenyl)-butyric acid 855223-27-7 C12H16O3
4-(2-hydroxy-3,4-dimethyl-phenyl)-butyric acid
—— 4-Allyl-2,3-dimethyl-phenol 3727-18-2 C11H14O
4-Allyl-2,3-dimethyl-phenol
—— 5-Allyl-2,3-dimethylphenol 40793-87-1 C11H14O
5-Allyl-2,3-dimethylphenol
—— methyl (4Z)-1-ethyl-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate 5955-40-8 C17H19NO5
methyl (4Z)-1-ethyl-4-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxopyrrole-3-carboxylate
—— 4,6-diiodo-2,3-dimethyl-phenol 17938-68-0 C8H8I2O
4,6-diiodo-2,3-dimethyl-phenol
—— bis(5-tert-butyl-2-furyl)(2-hydroxy-5-nitrophenyl)methane 1313199-65-3 C23H27NO5
bis(5-tert-butyl-2-furyl)(2-hydroxy-5-nitrophenyl)methane
—— 3-Methyl-4,6-di-t-butyl-2-nitrophenol 3114-65-6 C15H23NO3
3-Methyl-4,6-di-t-butyl-2-nitrophenol
—— (5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 5963-82-6 C18H13FN2O5
(5E)-1-(4-fluorophenyl)-5-(4-hydroxy-3-methoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
—— N-[(E)-(2-chlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide 329047-62-3 C14H11ClN2O4
N-[(E)-(2-chlorophenyl)methylideneamino]-3,4,5-trihydroxybenzamide
—— (5E)-1-(4-bromo-3-methylphenyl)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione 6063-89-4 C19H14BrClN2O5
(5E)-1-(4-bromo-3-methylphenyl)-5-[(5-chloro-2-hydroxy-3-methoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
—— methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate 6132-61-2 C21H20N2O5
methyl (4Z)-4-[(2-hydroxy-3-methoxyphenyl)methylidene]-2-methyl-5-oxo-1-(pyridin-3-ylmethyl)pyrrole-3-carboxylate
—— 1-methyl-2-(4-hydroxyphenyl)-1H-imidazoline 137208-88-9 C10H12N2O
1-methyl-2-(4-hydroxyphenyl)-1H-imidazoline
—— (5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-nitrophenyl)-2-thioxo-1,3-thiazolidin-4-one 6529-70-0 C18H14N2O6S2
(5E)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-3-(4-nitrophenyl)-2-thioxo-1,3-thiazolidin-4-one
—— 5-((4aR,7aS)-2-amino-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-7a-yl)-2-fluorophenol 1262038-94-7 C13H15FN2OS
5-((4aR,7aS)-2-amino-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-7a-yl)-2-fluorophenol
—— tert-butyl (4aR,7aS)-7a-(4-fluoro-3-hydroxyphenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-ylcarbamate 1262038-95-8 C18H23FN2O3S
tert-butyl (4aR,7aS)-7a-(4-fluoro-3-hydroxyphenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-ylcarbamate
—— 3, 5-di-tert-butyl-2-methoxyphenol 34896-15-6 C15H24O2
3, 5-di-tert-butyl-2-methoxyphenol
—— N,N-diethyl-2-hydroxy-3-methylbenzenecarbothioamide 141079-78-9 C12H17NOS
N,N-diethyl-2-hydroxy-3-methylbenzenecarbothioamide
—— 2,6-Dimethyl-4-(2-pyridin-3-yl-vinyl)-phenol 127035-56-7 C15H15NO
2,6-Dimethyl-4-(2-pyridin-3-yl-vinyl)-phenol
—— 6-Chlor-3,5-di-tert.-butyl-brenzcatechin 68093-59-4 C14H21ClO2
6-Chlor-3,5-di-tert.-butyl-brenzcatechin
—— Tetrabutyl ammonium, salt with 4-nitropyrocateco 11072-43-8 C22H40N2O4
Tetrabutyl ammonium, salt with 4-nitropyrocateco
—— 4,6-bis(5-carboxy-3-ethyl-4-methyl-2-pyrrolylmethyl)-1,3-dihydroxybenzene 675608-61-4 C24H28N2O6
4,6-bis(5-carboxy-3-ethyl-4-methyl-2-pyrrolylmethyl)-1,3-dihydroxybenzene
—— 4-[3-Hydroxypropoxy-di(propan-2-yl)silyl]phenol 211504-72-2 C15H26O3Si
4-[3-Hydroxypropoxy-di(propan-2-yl)silyl]phenol
—— (4-hydroxyphenyl)diphenylsulfonium chloride 345580-98-5 C18H15OS*Cl
(4-hydroxyphenyl)diphenylsulfonium chloride
—— 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetrakis[(dihydroxyphosphoryl)methyl]pentacyclo[19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>15,19</sup>]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene 878000-39-6 C32H36O20P4
4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetrakis[(dihydroxyphosphoryl)methyl]pentacyclo[19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>15,19</sup>]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene
—— tert-butyl (3-chloro-4-hydroxy-5-methylbenzyl)carbamate 852815-48-6 C13H18ClNO3
tert-butyl (3-chloro-4-hydroxy-5-methylbenzyl)carbamate
—— 1,1-dimethylethyl [(4-hydroxy-3-methylphenyl)methyl]carbamate 343322-76-9 C13H19NO3
1,1-dimethylethyl [(4-hydroxy-3-methylphenyl)methyl]carbamate
—— 2-prenylresorcin 34038-86-3 C11H14O2
2-prenylresorcin
—— dimethyl-4-hydroxyphenylsulfonium hexafluoroarsenate 120397-55-9 AsF6*C8H11OS
dimethyl-4-hydroxyphenylsulfonium hexafluoroarsenate
—— (5Z,5'Z)-2,2'-[ethane-1,2-diylbis(oxyethane-2,1-diylimino)]bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one) 1415582-32-9 C26H26N4O6S2
(5Z,5'Z)-2,2'-[ethane-1,2-diylbis(oxyethane-2,1-diylimino)]bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one)
—— (5Z,5'Z)-2,2'-(pentane-1,5-diyldiimino)bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one) 1415582-26-1 C25H24N4O4S2
(5Z,5'Z)-2,2'-(pentane-1,5-diyldiimino)bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one)
—— (5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]ethyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-1,3-thiazol-4(5H)-one 1415582-54-5 C27H25N7O4S2
(5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]ethyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-1,3-thiazol-4(5H)-one
—— (5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)ethyl]amino}-1,3-thiazol-4(5H)-one 1415582-51-2 C25H21N7O4S2
(5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)ethyl]amino}-1,3-thiazol-4(5H)-one
—— (5Z,5'Z)-2,2'-(nonane-1,9-diyldiimino)bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one) 1415582-30-7 C29H32N4O4S2
(5Z,5'Z)-2,2'-(nonane-1,9-diyldiimino)bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one)
—— (5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-1,3-thiazol-4(5H)-one 1415582-53-4 C26H23N7O4S2
(5Z,5'Z)-5-(4-hydroxybenzylidene)-2-{[2-(4-{[(5-(4-hydroxybenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]methyl}-1H-1,2,3-triazol-1-yl)propyl]amino}-1,3-thiazol-4(5H)-one
—— (5Z,5'Z)-2,2'-(octane-1,8-diyldiimino)bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one) 1415582-29-4 C28H30N4O4S2
(5Z,5'Z)-2,2'-(octane-1,8-diyldiimino)bis(5-(4-hydroxybenzylidene)-1,3-thiazol-4(5H)-one)
—— 1-(2',6'-dihydroxyphenyl)-3-methyl-but-2-en-1-one 130715-58-1 C11H12O3
1-(2',6'-dihydroxyphenyl)-3-methyl-but-2-en-1-one
—— bis-(5-bromo-2-hydroxy-benzylidene)-p-phenylenediamine 111610-60-7 C20H14Br2N2O2
bis-(5-bromo-2-hydroxy-benzylidene)-p-phenylenediamine
—— 1,3-bis(2-hydroxy-5-methylphenyl)tetrahydro-2-pyrimidinone 84379-39-5 C18H20N2O3
1,3-bis(2-hydroxy-5-methylphenyl)tetrahydro-2-pyrimidinone
—— 4,6-bis(dimethylaminomethyl)-2-nitrophenol 127396-47-8 C12H19N3O3
4,6-bis(dimethylaminomethyl)-2-nitrophenol
—— 1,1-dimethylethyl 2-[(3-bromo-5-chloro-2-hydroxyphenyl)methyl]hydrazinecarboxylate 1048992-88-6 C12H16BrClN2O3
1,1-dimethylethyl 2-[(3-bromo-5-chloro-2-hydroxyphenyl)methyl]hydrazinecarboxylate
—— N'-(5-chloro-2-hydroxybenzyl)hydrazinecarboxylic acid tert-butyl ester 913566-75-3 C12H17ClN2O3
N'-(5-chloro-2-hydroxybenzyl)hydrazinecarboxylic acid tert-butyl ester