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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
—— 2-(Oxiran-2-ylmethoxymethyl)oxirane;phenol;tricyclo[5.2.1.02,6]deca-3,8-diene —— C22H28O4
2-(Oxiran-2-ylmethoxymethyl)oxirane;phenol;tricyclo[5.2.1.02,6]deca-3,8-diene
—— 2,3-Dimethylphenol;prop-1-ene;styrene 76584-98-0 C28H42O
2,3-Dimethylphenol;prop-1-ene;styrene
—— Einecs 281-631-0 84000-74-8 C11H17N3O5
Einecs 281-631-0
—— N-(3,5-dibromo-4-hydroxyphenethyl)-N-methylacetamide 1207456-10-7 C11H13Br2NO2
N-(3,5-dibromo-4-hydroxyphenethyl)-N-methylacetamide
—— 5-Amino-2-methylphenol sulfate 10422-66-9 C7H11NO5S
5-Amino-2-methylphenol sulfate
—— (5Z)-2-{[2-(dimethylamino)ethyl]amino}-5-(5-fluoro-2-hydroxybenzylidene)-1,3-thiazol-4(5H)-one 1181081-59-3 C14H16FN3O2S
(5Z)-2-{[2-(dimethylamino)ethyl]amino}-5-(5-fluoro-2-hydroxybenzylidene)-1,3-thiazol-4(5H)-one
—— (R)-2-cyclohexyl-1-(2-hydroxy-5-methylphenyl)-2,3-dihydropyridin-4(1H)-one 1113034-35-7 C18H23NO2
(R)-2-cyclohexyl-1-(2-hydroxy-5-methylphenyl)-2,3-dihydropyridin-4(1H)-one
—— (E)-4-methoxy-2-(pent-2-en-2-yl)phenol 1186642-28-3 C12H16O2
(E)-4-methoxy-2-(pent-2-en-2-yl)phenol
—— (S)-1-(2-hydroxy-5-methylphenyl)-2-isobutyl-2,3-dihydropyridin-4(1H)-one 1113034-43-7 C16H21NO2
(S)-1-(2-hydroxy-5-methylphenyl)-2-isobutyl-2,3-dihydropyridin-4(1H)-one
—— (R)-1-(2-hydroxy-5-methylphenyl)-2-isopropyl-2,3-dihydropyridin-4(1H)-one 1113034-39-1 C15H19NO2
(R)-1-(2-hydroxy-5-methylphenyl)-2-isopropyl-2,3-dihydropyridin-4(1H)-one
—— 6-[2-(4-hydroxy-phenyl)-propyl]-pyridin-3-ol 1187188-71-1 C14H15NO2
6-[2-(4-hydroxy-phenyl)-propyl]-pyridin-3-ol
—— (3-Allyl-4-hydroxy-5-methoxybenzyl)formamide 1201633-46-6 C12H15NO3
(3-Allyl-4-hydroxy-5-methoxybenzyl)formamide
—— 5-[1-(3-hydroxyphenyl)meth-(Z)-ylidene]-4-methoxy-3-phenyl-1,5-dihydropyrrol-2-one 1202075-94-2 C18H15NO3
5-[1-(3-hydroxyphenyl)meth-(Z)-ylidene]-4-methoxy-3-phenyl-1,5-dihydropyrrol-2-one
—— 2-(2-hydroxyphenyl)-5-methyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3,4-thiadiazol-3(2H)-carboxamide 1190129-01-1 C13H13N5O2S2
2-(2-hydroxyphenyl)-5-methyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3,4-thiadiazol-3(2H)-carboxamide
—— 2-[1-(2-hydroxyphenyl)-3,5-dimethoxycyclohexa-2,5-dienyl]acetonitrile 1178546-47-8 C16H17NO3
2-[1-(2-hydroxyphenyl)-3,5-dimethoxycyclohexa-2,5-dienyl]acetonitrile
—— Dopexamin hydrochloride 86484-91-5 C22H33ClN2O2
Dopexamin hydrochloride
—— (S)-(4-Hydroxy-phenyl)-(S)-piperidin-2-yl-acetic acid methyl ester; hydrochloride 54593-35-0 C14H19NO3
(S)-(4-Hydroxy-phenyl)-(S)-piperidin-2-yl-acetic acid methyl ester; hydrochloride
—— 2-hydroxy-5-nitro-N-tetradecylbenzamide 124071-17-6 C21H34N2O4
2-hydroxy-5-nitro-N-tetradecylbenzamide
—— (+/-)-Th 1206 18866-78-9 C12H19NO3*H
(+/-)-Th 1206
—— N-dodecyl-2-hydroxy-5-nitrobenzamide 124071-21-2 C19H30N2O4
N-dodecyl-2-hydroxy-5-nitrobenzamide
—— 5-chloro-2-hydroxy-3-nitro-N-tetradecylbenzamide 124071-19-8 C21H33ClN2O4
5-chloro-2-hydroxy-3-nitro-N-tetradecylbenzamide
—— Deterenol, (R)- 29170-05-6 C11H17NO2
Deterenol, (R)-
—— 5-<6-(2,3-dihydroxyphenyl)hexyl>-3-methyl-2-dihydrofuranone 81464-94-0 C17H24O4
5-<6-(2,3-dihydroxyphenyl)hexyl>-3-methyl-2-dihydrofuranone
—— 1-Ethyl-1-[3-(4-hydroxy-3-methoxyphenyl)propyl]-3-(2-phenylethyl)thiourea 545442-99-7 C21H28N2O2S
1-Ethyl-1-[3-(4-hydroxy-3-methoxyphenyl)propyl]-3-(2-phenylethyl)thiourea
—— 2-Methoxy-5-[5-(3,4,5-trimethoxy-phenyl)-[1,2,3]thiadiazol-4-yl]-phenol 916165-29-2 C18H18N2O5S
2-Methoxy-5-[5-(3,4,5-trimethoxy-phenyl)-[1,2,3]thiadiazol-4-yl]-phenol
—— 4-(5-chloro-2,4-dihydroxyphenyl)-5-(4-methoxyphenyl)-1,2,3-thiadiazole 1141896-17-4 C15H11ClN2O3S
4-(5-chloro-2,4-dihydroxyphenyl)-5-(4-methoxyphenyl)-1,2,3-thiadiazole
—— (R)-ypaoamide 1190851-15-0 C26H36N2O5
(R)-ypaoamide
—— 5-[2-(3,5-dihydroxyphenyl)ethyl]-3-isoxazolecarboxylic acid ethyl ester 1189360-75-5 C14H15NO5
5-[2-(3,5-dihydroxyphenyl)ethyl]-3-isoxazolecarboxylic acid ethyl ester
—— 3,5-Dideuterio-4-hydroxy-2,6-bis(trideuteriomethyl)benzonitrile 1207102-01-9 C9H9NO
3,5-Dideuterio-4-hydroxy-2,6-bis(trideuteriomethyl)benzonitrile
—— 3-fluoro-5-[5-(4-hydroxyphenyl)-2-thienyl]phenol 1193524-77-4 C16H11FO2S
3-fluoro-5-[5-(4-hydroxyphenyl)-2-thienyl]phenol
—— 2-fluoro-5-[5-(4-hydroxyphenyl)-2-thienyl]phenol 1193524-81-0 C16H11FO2S
2-fluoro-5-[5-(4-hydroxyphenyl)-2-thienyl]phenol
—— 2-fluoro-4-[5-(4-fluoro-3-hydroxyphenyl)thien-2-yl]phenol 1193524-99-0 C16H10F2O2S
2-fluoro-4-[5-(4-fluoro-3-hydroxyphenyl)thien-2-yl]phenol
—— N-(3-[5-(3-hydroxyphenyl)-2-thienyl]benzyl)methanesulfonamide 1193524-64-9 C18H17NO3S2
N-(3-[5-(3-hydroxyphenyl)-2-thienyl]benzyl)methanesulfonamide
—— 5-(3-Hydroxy-4-methoxyphenyl)-5-methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one 1092388-61-8 C18H18N2O3
5-(3-Hydroxy-4-methoxyphenyl)-5-methyl-2-phenyl-4,5-dihydropyridazin-3(2H)-one
—— 4-chloro-3-fluoro-5-methoxyphenol 920036-40-4 C7H6ClFO2
4-chloro-3-fluoro-5-methoxyphenol
—— [2-(6-allyloxy-2-bromo-3-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester 1203905-07-0 C16H22BrNO4
[2-(6-allyloxy-2-bromo-3-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester
—— 4-Methoxy-2-(3-propan-2-ylideneinden-1-yl)phenol 1202185-94-1 C19H18O2
4-Methoxy-2-(3-propan-2-ylideneinden-1-yl)phenol
—— 3,4,5-trihydroxy-N-octadecylbenzamide 87667-26-3 C25H43NO4
3,4,5-trihydroxy-N-octadecylbenzamide
—— Docosyl 3,4,5-trihydroxybenzamide 109462-52-4 C29H51NO4
Docosyl 3,4,5-trihydroxybenzamide
—— (E)-N-Hydroxy-5-(2-hydroxy-3-methoxystyryl)furan-2-carboxamide 1019734-16-7 C14H13NO5
(E)-N-Hydroxy-5-(2-hydroxy-3-methoxystyryl)furan-2-carboxamide
—— 3-methoxy-6-[(1,2,3-trimethoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)methyl]benzene-1,2-diol 1073537-25-3 C22H28O6
3-methoxy-6-[(1,2,3-trimethoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)methyl]benzene-1,2-diol
—— 3-(10-Heptadecenyl)phenol 111047-33-7 C23H38O
3-(10-Heptadecenyl)phenol
—— 2-Cyano-3-(4-hydroxy-phenyl)-but-2-enedinitrile 72971-39-2 C11H5N3O
2-Cyano-3-(4-hydroxy-phenyl)-but-2-enedinitrile
—— (E)-1-(5-butoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one 1067559-86-7 C18H20O3S
(E)-1-(5-butoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
—— (E)-1-(2-hydroxy-5-propoxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one 1067559-74-3 C17H18O3S
(E)-1-(2-hydroxy-5-propoxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
—— (E)-1-(5-ethoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one 1067559-63-0 C16H16O3S
(E)-1-(5-ethoxy-2-hydroxyphenyl)-3-(5-methylthiophen-2-yl)prop-2-en-1-one
—— 4-([5-(3-hydroxy-4-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid 1148127-01-8 C25H20N2O5S
4-([5-(3-hydroxy-4-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid
—— (E)-6-fluoro-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one 1148119-13-4 C16H12FNO3
(E)-6-fluoro-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one
—— 4-([5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid 1148127-02-9 C25H20N2O5S
4-([5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid
—— 2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide 1039558-89-8 C13H12N2O5S
2-[(5Z)-5-[(3-hydroxy-4-methoxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetamide