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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
—— 4-chloro-N-[(2-hydroxy-4-methoxyphenyl)methylideneamino]benzamide 341980-22-1 C15H13ClN2O3
4-chloro-N-[(2-hydroxy-4-methoxyphenyl)methylideneamino]benzamide
—— (+)-trans-(R,R)-[2-(2-cyclopropyImethyloxy-5-hydroxyphenyl)cycIopropylmethyl]carbamic acid tert-butyl ester 1322700-05-9 C19H27NO4
(+)-trans-(R,R)-[2-(2-cyclopropyImethyloxy-5-hydroxyphenyl)cycIopropylmethyl]carbamic acid tert-butyl ester
—— 2,3,6-trimethyl-4-[(diisopropylphenylsilyl)methylthio]phenol 1230389-47-5 C22H32OSSi
2,3,6-trimethyl-4-[(diisopropylphenylsilyl)methylthio]phenol
—— 4,5-Bis(furan-2-yl)-2-[(2-hydroxyphenyl)methylideneamino]furan-3-carbonitrile 75861-37-9 C20H12N2O4
4,5-Bis(furan-2-yl)-2-[(2-hydroxyphenyl)methylideneamino]furan-3-carbonitrile
—— 3,6,9,17,20,23-Hexaoxatricyclo<23.3.1.1<sup>11,15</sup>>triaconta-1(29),11,13,15(30),25,27-hexaene-29,30-diol 143634-91-7 C24H32O8
3,6,9,17,20,23-Hexaoxatricyclo<23.3.1.1<sup>11,15</sup>>triaconta-1(29),11,13,15(30),25,27-hexaene-29,30-diol
—— 2-hydroxy-5-methylisophthalaldehyde bis(p-methoxy thiobenzoylhydrazone) 488823-83-2 C25H24N4O3S2
2-hydroxy-5-methylisophthalaldehyde bis(p-methoxy thiobenzoylhydrazone)
—— tert-butyl 2-[3,5-di(tert-butyl)-4-hydroxyphenoxy]ethyl(4-nitrophenethyl)carbamate 262614-45-9 C29H42N2O6
tert-butyl 2-[3,5-di(tert-butyl)-4-hydroxyphenoxy]ethyl(4-nitrophenethyl)carbamate
—— 3-Diphenylphosphanyl-3-(4-hydroxy-3,5-dimethoxyphenyl)propanal 1159262-04-0 C23H23O4P
3-Diphenylphosphanyl-3-(4-hydroxy-3,5-dimethoxyphenyl)propanal
—— 4,6-Dinitro-2-(1-propyloctyl)-phenol 17508-88-2 C17H26N2O5
4,6-Dinitro-2-(1-propyloctyl)-phenol
—— 3-(Dibutyl-ethyl-silanyloxymethyl)-phenol 79535-46-9 C17H30O2Si
3-(Dibutyl-ethyl-silanyloxymethyl)-phenol
—— (S,1'S)-2-hydroxy-5-methoxy-α-<1'-Boc-2'-aminoethyl>benzenemethanol 123172-82-7 C15H23NO5
(S,1'S)-2-hydroxy-5-methoxy-α-<1'-Boc-2'-aminoethyl>benzenemethanol
—— 1-Methyl-α-phenyl-2-piperidylcarbinol 32511-72-1 C13H19NO2
1-Methyl-α-phenyl-2-piperidylcarbinol
—— 3-[2-(2-hydroxyphenyl)ethyl]-5-methyl-5-phenyl-4,5-dihydroisoxazole 1158558-30-5 C18H19NO2
3-[2-(2-hydroxyphenyl)ethyl]-5-methyl-5-phenyl-4,5-dihydroisoxazole
—— N-(4-pyridylmethylidene)-4-amino-2,6-dibromophenol 190844-72-5 C12H8Br2N2O
N-(4-pyridylmethylidene)-4-amino-2,6-dibromophenol
—— 2,6-bis(N-[(2-dimethylamino)ethyl]iminomethyl)-4-methylphenol 96594-20-6 C17H28N4O
2,6-bis(N-[(2-dimethylamino)ethyl]iminomethyl)-4-methylphenol
—— (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoic acid 1381771-95-4 C15H13NO4
(E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoic acid
—— 3,5-Dibrom-α,α-bis-(trifluormethyl)-4-hydroxy-benzylalkohol 16867-84-8 C9H4Br2F6O2
3,5-Dibrom-α,α-bis-(trifluormethyl)-4-hydroxy-benzylalkohol
—— Bis-(2-hydroxy-5-fluor-phenyl)-trisulfid 732-90-1 C12H8F2O2S3
Bis-(2-hydroxy-5-fluor-phenyl)-trisulfid
—— 4-ethyl-2-bromo-6-methoxy-3-methyl-phenol 857831-73-3 C10H13BrO2
4-ethyl-2-bromo-6-methoxy-3-methyl-phenol
—— 2-(2-Thienylmethyl)-1,4-benzenediol 205653-04-9 C11H10O2S
2-(2-Thienylmethyl)-1,4-benzenediol
—— methyl 7-(4-hydroxyphenyl)-7-<<(methoxyethoxy)methyl>oxy>-3-oxoheptanoate 127461-72-7 C18H26O7
methyl 7-(4-hydroxyphenyl)-7-<<(methoxyethoxy)methyl>oxy>-3-oxoheptanoate
—— N'-(2-Chloro-3-hydroxy-benzyl)-hydrazinecarboxylic acid ethyl ester 90875-59-5 C10H13ClN2O3
N'-(2-Chloro-3-hydroxy-benzyl)-hydrazinecarboxylic acid ethyl ester
—— [(3-Hydroxy-4-methoxy-benzimidoyl)-aminooxy]-acetic acid ethyl ester 63409-80-3 C12H16N2O5
[(3-Hydroxy-4-methoxy-benzimidoyl)-aminooxy]-acetic acid ethyl ester
—— 2-Hydroxy-6-nitrobenzylbromid 57356-30-6 C7H6BrNO3
2-Hydroxy-6-nitrobenzylbromid
—— 4-(2-Hydroxy-3-methylamino-propoxy)-phenol 19096-48-1 C10H15NO3
4-(2-Hydroxy-3-methylamino-propoxy)-phenol
—— 3,4-bis(tridecyloxy)phenol 1277180-67-2 C32H58O3
3,4-bis(tridecyloxy)phenol
—— N-Fumaryl-3,5-dimethoxy-4-hydroxyphenylethylamin-ethylester 54738-23-7 C16H21NO6
N-Fumaryl-3,5-dimethoxy-4-hydroxyphenylethylamin-ethylester
—— 5-{[1-(benzo[d][1,3]dioxol-5-yl)-1H-tetrazol-5-yl](benzylamino)methyl}-2-methoxyphenol 1268445-53-9 C23H21N5O4
5-{[1-(benzo[d][1,3]dioxol-5-yl)-1H-tetrazol-5-yl](benzylamino)methyl}-2-methoxyphenol
—— N-[(2-hydroxy-5-nitrophenyl)methylideneamino]thiophene-2-carboxamide 304864-31-1 C12H9N3O4S
N-[(2-hydroxy-5-nitrophenyl)methylideneamino]thiophene-2-carboxamide
—— 5-(heptyloxy)-2-hydroxybenzaldehyde 291507-17-0 C14H20O3
5-(heptyloxy)-2-hydroxybenzaldehyde
—— 2-bromo-4-cyclopentylphenol 55910-49-1 C11H13BrO
2-bromo-4-cyclopentylphenol
—— 3,4-bis-(2-hydroxy-phenyl)-cyclobutane-1,2-dicarboxylic acid dimethyl ester 85381-10-8 C20H20O6
3,4-bis-(2-hydroxy-phenyl)-cyclobutane-1,2-dicarboxylic acid dimethyl ester
—— Brenzcatechyl-phosphorigsaureester-n-butylamid 51439-11-3 C10H14NO2P
Brenzcatechyl-phosphorigsaureester-n-butylamid
—— 1315577-53-7 C16H22O3
—— 4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butanoic acid 4-(4S,7R,8S,9S,13Z,16S)-[7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yloxycarbonyloxymethyl]-2-nitro-phenyl ester 658054-52-5 C52H67N3O13SSi
4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butanoic acid 4-(4S,7R,8S,9S,13Z,16S)-[7-allyl-4-(tert-butyl-dimethyl-silanyloxy)-5,5,9,13-tetramethyl-16-(2-methyl-benzothiazol-5-yl)-2,6-dioxo-oxacyclohexadec-13-en-8-yloxycarbonyloxymethyl]-2-nitro-phenyl ester
—— (3S,4R,5R)-3,4-dihydroxy-1,3-dimethyl-5-[(4-phenylmethoxyphenyl)methyl]pyrrolidin-2-one 1370332-22-1 C20H23NO4
(3S,4R,5R)-3,4-dihydroxy-1,3-dimethyl-5-[(4-phenylmethoxyphenyl)methyl]pyrrolidin-2-one
—— 3-(1-Aminocyclobutyl)-4-bromophenol 1314698-96-8 C10H12BrNO
3-(1-Aminocyclobutyl)-4-bromophenol
—— 1-(2-Hydroxy-4-methoxy-phenyl)-dodecan-1-one oxime 143286-65-1 C19H31NO3
1-(2-Hydroxy-4-methoxy-phenyl)-dodecan-1-one oxime
—— 4-methoxy-3-(2-nitro-5-hydroxybenzylidene)phthalide 887645-05-8 C16H11NO6
4-methoxy-3-(2-nitro-5-hydroxybenzylidene)phthalide
—— 881672-53-3 C15H22O4
—— Phenol, 2,6-dibromo-4-[[(2-hydroxyphenyl)methylene]amino]- 112092-96-3 C13H9Br2NO2
Phenol, 2,6-dibromo-4-[[(2-hydroxyphenyl)methylene]amino]-
—— 3-(2.4-Dihydroxy-phenyl)-5-(5-brom-2.4-dihydroxy-phenyl)isooxazol 19743-27-2 C15H10BrNO5
3-(2.4-Dihydroxy-phenyl)-5-(5-brom-2.4-dihydroxy-phenyl)isooxazol
—— 2-Fluoro-6-iodo-4-methylphenol 491862-87-4 C7H6FIO
2-Fluoro-6-iodo-4-methylphenol
—— 5-Methyl-2-((S)-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-phenol 120409-54-3 C15H22O2
5-Methyl-2-((S)-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-phenol
—— 92551-38-7 C15H15ClN2O2
—— 4-(3-methyl-[1,4]oxazepan-2-yl)-benzene-1,2-diol 96196-19-9 C12H17NO3
4-(3-methyl-[1,4]oxazepan-2-yl)-benzene-1,2-diol
—— tert-butyl (2S)-2-[(S)-hydroxy-(2-hydroxy-5-methoxyphenyl)methyl]pyrrolidine-1-carboxylate 123172-77-0 C17H25NO5
tert-butyl (2S)-2-[(S)-hydroxy-(2-hydroxy-5-methoxyphenyl)methyl]pyrrolidine-1-carboxylate
—— 4-methoxy-2-((trifluoromethyl)thio)phenol 20038-80-6 C8H7F3O2S
4-methoxy-2-((trifluoromethyl)thio)phenol
—— 6-(2-hydroxy-4-methoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-one 132124-44-8 C11H12N2O3
6-(2-hydroxy-4-methoxyphenyl)-2,3,4,5-tetrahydropyridazin-3-one
—— (4Z)-4-(4-hydroxy-3,5-dimethoxybenzylidene)-2-phenyloxazol-5(4H)-one 1344054-06-3 C18H15NO5
(4Z)-4-(4-hydroxy-3,5-dimethoxybenzylidene)-2-phenyloxazol-5(4H)-one