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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
—— 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
—— 4-(2-Benzylamino-ethyl)-2-methoxy-phenol 107044-61-1 C16H19NO2
4-(2-Benzylamino-ethyl)-2-methoxy-phenol
—— 3-(4-Hydroxy-2-methoxyphenyl)-2-propenal 127321-19-1 C10H10O3
3-(4-Hydroxy-2-methoxyphenyl)-2-propenal
—— 4,5-dinitro-2-[β-(2-hydroxyethoxy)ethoxy]phenol 105780-37-8 C10H12N2O8
4,5-dinitro-2-[β-(2-hydroxyethoxy)ethoxy]phenol
—— 3-allyl-2,6-dimethylphenol 41389-60-0 C11H14O
3-allyl-2,6-dimethylphenol
—— 4-(4-Hydroxy-3-methoxyphenyl)butan-2-one oxime —— C11H15NO3
4-(4-Hydroxy-3-methoxyphenyl)butan-2-one oxime
—— 1-(2-hydroxy-5-methyl-phenyl)-hex-2-en-1-one 41873-82-9 C13H16O2
1-(2-hydroxy-5-methyl-phenyl)-hex-2-en-1-one
—— 2,2-dimethyl-propionic acid 4-[2-(3-chloro-propoxy)-ethyl]phenyl ester 890042-62-3 C16H23ClO3
2,2-dimethyl-propionic acid 4-[2-(3-chloro-propoxy)-ethyl]phenyl ester
—— 4-[2-(3-chloro-propoxy)-ethyl]-phenol 890042-61-2 C11H15ClO2
4-[2-(3-chloro-propoxy)-ethyl]-phenol
—— 3,4-dimethoxy-9-(3',5'-dimethoxy-4'-hydroxyphenyl)-6,7-dihydro-5H-benzo[7]annulene 1378239-12-3 C21H24O5
3,4-dimethoxy-9-(3',5'-dimethoxy-4'-hydroxyphenyl)-6,7-dihydro-5H-benzo[7]annulene
—— 3-methoxy-4-hydroxy-9-(3',4'-dihydroxy-5'-methoxyphenyl)-6,7-dihydro-5H-benzo[7]annulene 1378239-13-4 C19H20O5
3-methoxy-4-hydroxy-9-(3',4'-dihydroxy-5'-methoxyphenyl)-6,7-dihydro-5H-benzo[7]annulene
—— 9-(4'-Hydroxy-3',5'-dimethoxyphenyl)-3-methoxy-6,7-dihydro-5H-benzo[7]annulen-4-ol 1378239-11-2 C20H22O5
9-(4'-Hydroxy-3',5'-dimethoxyphenyl)-3-methoxy-6,7-dihydro-5H-benzo[7]annulen-4-ol
—— (2E)-9-azabicyclo[6.1.0]non-2-ene;2,4,6-trinitrophenol 16484-15-4 C14H16N4O7
(2E)-9-azabicyclo[6.1.0]non-2-ene;2,4,6-trinitrophenol
—— 4-chloro-3,5-dimethoxytoluene-2-ol 113523-87-8 C9H11ClO3
4-chloro-3,5-dimethoxytoluene-2-ol
—— 2-dodecyl-5-methyl-resorcinol monomethyl ether 60488-44-0 C20H34O2
2-dodecyl-5-methyl-resorcinol monomethyl ether
—— 2-dodecylorcinol 60488-55-3 C19H32O2
2-dodecylorcinol
—— 4-bromo-3-methoxy-5-methylphenol 34132-37-1 C8H9BrO2
4-bromo-3-methoxy-5-methylphenol
—— 2-bromo-3-hydroxy-5-methoxytoluene 34132-31-5 C8H9BrO2
2-bromo-3-hydroxy-5-methoxytoluene
—— 2-[(1R)-1-hydroxybut-3-enyl]phenol 1000781-28-1 C10H12O2
2-[(1R)-1-hydroxybut-3-enyl]phenol
—— ε-aminocaproyl-tyramine hydrochloride 76763-08-1 C14H22N2O2*ClH
ε-aminocaproyl-tyramine hydrochloride
—— 2-[(1S)-1-hydroxybut-3-enyl]phenol 1000781-27-0 C10H12O2
2-[(1S)-1-hydroxybut-3-enyl]phenol