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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-hydroxy-5-(3-hydroxy-propyl)-3-methoxy-benzaldehyde 6245-54-1 C11H14O4
2-hydroxy-5-(3-hydroxy-propyl)-3-methoxy-benzaldehyde
—— 3,4-bis-(5-chloro-2-hydroxy-benzylidenamino)-2,2-dimethyl-butan-1-ol 102461-68-7 C20H22Cl2N2O3
3,4-bis-(5-chloro-2-hydroxy-benzylidenamino)-2,2-dimethyl-butan-1-ol
—— 2-Amino-4-<2-hydroxy-4-aethyl-phenyl>-thiazol 100060-15-9 C11H12N2OS
2-Amino-4-<2-hydroxy-4-aethyl-phenyl>-thiazol
—— 4-(4,5-Dihydro-1,3-oxazol-2-yl)-2-fluorophenol 98033-92-2 C9H8FNO2
4-(4,5-Dihydro-1,3-oxazol-2-yl)-2-fluorophenol
—— 2-(((1H-tetrazol-5-yl)imino)methyl)-4-bromophenol 129587-42-4 C8H6BrN5O
2-(((1H-tetrazol-5-yl)imino)methyl)-4-bromophenol
—— 1-Hydroxy-2-methoxy-4-<2-hydroxy-1-p-toluolsulfonyl-aethyl>-benzol 3795-80-0 C16H18O5S
1-Hydroxy-2-methoxy-4-<2-hydroxy-1-p-toluolsulfonyl-aethyl>-benzol
—— 2-methyl-isonicotinic acid vanillylidenehydrazide 101091-68-3 C15H15N3O3
2-methyl-isonicotinic acid vanillylidenehydrazide
—— aniline; salt of 4-nitro-phenol 7274-03-5 C6H5NO3*C6H7N
aniline; salt of 4-nitro-phenol
—— Phenol, 2-[[(3-bromophenyl)imino]methyl]-4-chloro- 89046-30-0 C13H9BrClNO
Phenol, 2-[[(3-bromophenyl)imino]methyl]-4-chloro-
—— 3,3'-(3,4-dihydroxy-benzylidenedimercapto)-di-propionic acid 100613-80-7 C13H16O6S2
3,3'-(3,4-dihydroxy-benzylidenedimercapto)-di-propionic acid
—— 4-amidino-2-bromophenol trifluoroacetic acid salt 1311290-61-5 C2HF3O2*C7H7BrN2O
4-amidino-2-bromophenol trifluoroacetic acid salt
—— 2-(1-cyclohept-4-enyl-1-vinyl-alluloxymethyl)-phenol 697744-54-0 C19H24O2
2-(1-cyclohept-4-enyl-1-vinyl-alluloxymethyl)-phenol
—— 4-hydroxy-3-nitro-benzamidine hydrochloride 105450-74-6 C7H7N3O3*ClH
4-hydroxy-3-nitro-benzamidine hydrochloride
—— 3-Benzyl-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione 641591-67-5 C17H13NO4S
3-Benzyl-5-[(3,4-dihydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
—— 2-(4-Nitro-2-hydroxyphenylhydrazono)-buttersaeureaethylester 19169-39-2 C12H15N3O5
2-(4-Nitro-2-hydroxyphenylhydrazono)-buttersaeureaethylester
—— 2,4-di-sec-dodecylphenol 152606-37-6 C30H54O
2,4-di-sec-dodecylphenol
—— 2-[(2E)-2-[(3,4-dihydroxyphenyl)methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one 303024-34-2 C12H12N4O3
2-[(2E)-2-[(3,4-dihydroxyphenyl)methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one
—— 11-bromo-11-deoxyleudrin 116386-92-6 C15H15BrO8
11-bromo-11-deoxyleudrin
—— 2-(4-hydroxy-3-methoxy-phenyl)-acetimidic acid ethyl ester; hydrochloride 119851-51-3 C11H15NO3*ClH
2-(4-hydroxy-3-methoxy-phenyl)-acetimidic acid ethyl ester; hydrochloride
—— 6-chloro-3,4-dimethyl-2-(2-nitro-benzenesulfonyl)-phenol 106837-69-8 C14H12ClNO5S
6-chloro-3,4-dimethyl-2-(2-nitro-benzenesulfonyl)-phenol
—— 4-(ethyl-phenyl-phosphino)-phenol 857629-58-4 C14H15OP
4-(ethyl-phenyl-phosphino)-phenol
—— Ethylendaminobis-o-hydroxyphenylmethylphosphinsaeure 27334-00-5 C18H26N2O6P2
Ethylendaminobis-o-hydroxyphenylmethylphosphinsaeure
—— 5,11-dimethylcalix[4]arene 68803-66-7 C30H28O4
5,11-dimethylcalix[4]arene
—— bis-N,N'-salicylidene-2,6-bis-aminomethyl-pyridine 67455-83-8 C21H19N3O2
bis-N,N'-salicylidene-2,6-bis-aminomethyl-pyridine
—— 71313-82-1 C16H14Cl2N2O6S
—— phenyl N'-aminocarbamimidothioate;2,4,6-trinitrophenol 79163-06-7 C6H3N3O7*C7H9N3S
phenyl N'-aminocarbamimidothioate;2,4,6-trinitrophenol
—— raphanuside 1002127-43-6 C16H22O8S
raphanuside
—— 2-bromo-4-(4,5-dihydro-2-oxazolyl)phenol 105639-19-8 C9H8BrNO2
2-bromo-4-(4,5-dihydro-2-oxazolyl)phenol
—— 5-(bis(3,4,5-trihydroxyphenyl)methylene)furan-2(5H)-one 1218770-84-3 C17H12O8
5-(bis(3,4,5-trihydroxyphenyl)methylene)furan-2(5H)-one
—— 2-[[(1R,2R)-2-aminocyclohexyl]iminomethyl]-6-methoxyphenol 1067713-92-1 C14H20N2O2
2-[[(1R,2R)-2-aminocyclohexyl]iminomethyl]-6-methoxyphenol
—— N<sub>1</sub>-2-(2-hydroxy-3-methylbenzoyl)vinyl-N<sub>1</sub>-methylhydrazine 123532-16-1 C11H14N2O2
N<sub>1</sub>-2-(2-hydroxy-3-methylbenzoyl)vinyl-N<sub>1</sub>-methylhydrazine
—— 6-(5-amino-2-hydroxyphenyl)-5,5-dimethyl-4,5-dihydro-3(2H)-pyridazinone 483323-99-5 C12H15N3O2
6-(5-amino-2-hydroxyphenyl)-5,5-dimethyl-4,5-dihydro-3(2H)-pyridazinone
—— 3,5-dimethyl-4-(4-hydroxy-phenyl)-1,4,7,8-tetrahydro di pyrazolo[3,4-b;4',3'-e]pyridine 1346445-99-5 C15H15N5O
3,5-dimethyl-4-(4-hydroxy-phenyl)-1,4,7,8-tetrahydro di pyrazolo[3,4-b;4',3'-e]pyridine
—— (E)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-N-methylhydrazinecarbothioamide 1446891-97-9 C11H15N3O3S
(E)-2-(4-hydroxy-3,5-dimethoxybenzylidene)-N-methylhydrazinecarbothioamide
—— 4-allyl-2-methyl-1,3-benzenediol 166591-71-5 C10H12O2
4-allyl-2-methyl-1,3-benzenediol
—— 5-[5-(3,5-Dihydroxyphenyl)-4,4-dimethylpyrazol-3-yl]benzene-1,3-diol 1027382-96-2 C17H16N2O4
5-[5-(3,5-Dihydroxyphenyl)-4,4-dimethylpyrazol-3-yl]benzene-1,3-diol
—— 2-hydroxy-3-nitro-5-nonylbenzylidene octanoylhydrazone 1074213-36-7 C24H39N3O4
2-hydroxy-3-nitro-5-nonylbenzylidene octanoylhydrazone
—— (1R,4S,7S)-5-allyl-7-((S)-(4-hydroxy-3,5-dimethoxyphenyl)(methoxy)methyl)-1,3,3-trimethoxybicyclo[2.2.2]oct-5-en-2-one 66551-06-2 C24H32O8
(1R,4S,7S)-5-allyl-7-((S)-(4-hydroxy-3,5-dimethoxyphenyl)(methoxy)methyl)-1,3,3-trimethoxybicyclo[2.2.2]oct-5-en-2-one
—— (S)-4-(4-hydroxyphenyl)-oxazolidin-2-one 264281-16-5 C9H9NO3
(S)-4-(4-hydroxyphenyl)-oxazolidin-2-one
—— 2-hydroxy-3,5-dinitro-N-octylbenzamide 227946-85-2 C15H21N3O6
2-hydroxy-3,5-dinitro-N-octylbenzamide
—— <i>N</i>'-(2-hydroxy-benzylidene)-pyrazine-2-carbohydrazonic acid amide 31649-03-3 C12H11N5O
<i>N</i>'-(2-hydroxy-benzylidene)-pyrazine-2-carbohydrazonic acid amide
—— N-[(6-bromo-2-hydroxy-3-methoxyphenyl)methylideneamino]benzamide 1235837-33-8 C15H13BrN2O3
N-[(6-bromo-2-hydroxy-3-methoxyphenyl)methylideneamino]benzamide
—— (2-amino-4-hydroxy-5-methylphenyl)thiocarbonitrile 600135-20-4 C8H8N2OS
(2-amino-4-hydroxy-5-methylphenyl)thiocarbonitrile
—— 30,31,32,33-tetrahydroxy-7,19-dioctylhexacyclo[11.11.5.13,23.15,9.111,15.117,21]tritriaconta-1,3(30),5,7,9(33),11(32),12,14,17(31),18,20,23-dodecaen-27-one 137569-08-5 C49H62O5
30,31,32,33-tetrahydroxy-7,19-dioctylhexacyclo[11.11.5.13,23.15,9.111,15.117,21]tritriaconta-1,3(30),5,7,9(33),11(32),12,14,17(31),18,20,23-dodecaen-27-one
—— 2-(2-(2-hydroxycyclohexenyl)-2-oxoethyl)-3-chromonecarboxylic acid 76245-36-8 C18H20O6
2-(2-(2-hydroxycyclohexenyl)-2-oxoethyl)-3-chromonecarboxylic acid
—— 3-(adamantan-1-ylaminomethyl)benzene-1,2-diol 1306513-68-7 C17H23NO2
3-(adamantan-1-ylaminomethyl)benzene-1,2-diol
—— 1418095-97-2 C6H4F2O*C25H35NO
—— methyl 4-((3-hydroxy-2,5-dimethylphenyl)sulfanyl)-3-oxobutanoate 1452478-81-7 C13H16O4S
methyl 4-((3-hydroxy-2,5-dimethylphenyl)sulfanyl)-3-oxobutanoate
—— Methyl-4-(3-brom-4-hydroxyphenyl)-butyrat 22320-11-2 C11H13BrO3
Methyl-4-(3-brom-4-hydroxyphenyl)-butyrat
—— 3-Bromo-2-(dichloromethyl)phenol 86006-43-1 C7H5BrCl2O
3-Bromo-2-(dichloromethyl)phenol