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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
—— 5-(2-aminocyclohexyl)amino-7-(2,5-dihydroxy-4-methoxybenzyl)amino-3-isopropylpyrazolo[4,3-d]pyrimidine 607727-38-8 C22H31N7O3
5-(2-aminocyclohexyl)amino-7-(2,5-dihydroxy-4-methoxybenzyl)amino-3-isopropylpyrazolo[4,3-d]pyrimidine
—— 2,2'-Dihydroxy-4,6-dimethyl-5-chlor-3',5'-difluor-diphenylmethan 17246-05-8 C15H13ClF2O2
2,2'-Dihydroxy-4,6-dimethyl-5-chlor-3',5'-difluor-diphenylmethan
—— 2-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}-4-(methyloxy)phenol 1134198-02-9 C22H36N2O4
2-{[1-(trans-1-methyl-4-{[2-(methyloxy)ethyl]oxy}cyclohexyl)-4-piperidinyl]amino}-4-(methyloxy)phenol
—— N'-[2-(3,4-difluoro-5-methoxyphenyl)acetyl]-2-ethyl-4-hydroxy-3-methyl-benzohydrazide 1227845-38-6 C19H20F2N2O4
N'-[2-(3,4-difluoro-5-methoxyphenyl)acetyl]-2-ethyl-4-hydroxy-3-methyl-benzohydrazide
—— N<sup>1</sup>-benzylidene-N<sup>2</sup>-[3-(4-hydroxy-3-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 1380074-89-4 C23H19N3O4S
N<sup>1</sup>-benzylidene-N<sup>2</sup>-[3-(4-hydroxy-3-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine
—— 1-(2-Formyl-5-hydroxy-3-methoxy-4-methylphenyl)-methylbutanon 35052-00-7 C14H18O4
1-(2-Formyl-5-hydroxy-3-methoxy-4-methylphenyl)-methylbutanon
—— 5-nitro-2-((E)-((E)-3-phenylallylidene)amino)phenol 1187781-17-4 C15H12N2O3
5-nitro-2-((E)-((E)-3-phenylallylidene)amino)phenol
—— (1E,9E)-2,2'-[nonane-1,9-diylbis(nitrilomethylidyne)]diphenol 67232-08-0 C23H30N2O2
(1E,9E)-2,2'-[nonane-1,9-diylbis(nitrilomethylidyne)]diphenol
—— 4-(hex-5-yn-1-yloxy)phenol 402955-92-4 C12H14O2
4-(hex-5-yn-1-yloxy)phenol
—— 42546-11-2 C22H16N6O6
—— 2-(3-Butylsulfanyl-propyl)-phenol 17733-37-8 C13H20OS
2-(3-Butylsulfanyl-propyl)-phenol
—— N<sup>1</sup>-4-methylbenzylidene-N<sup>2</sup>-[3-(3-hydroxy-4-methoxyphenyl)-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazine 1380075-15-9 C24H19N3O4S
N<sup>1</sup>-4-methylbenzylidene-N<sup>2</sup>-[3-(3-hydroxy-4-methoxyphenyl)-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazine
—— 51084-54-9 C12H15N3O4S
—— 2-Methoxy-4-(2-nitro-1-trinitromethyl-propyl)-phenol 36697-34-4 C11H12N4O10
2-Methoxy-4-(2-nitro-1-trinitromethyl-propyl)-phenol
—— 4-Methoxy-3-tricosyl-phenol 144464-96-0 C30H54O2
4-Methoxy-3-tricosyl-phenol
—— methyl 5-(2-hydroxyphenyl)cyclopentene-1-carboxylate 137089-99-7 C13H14O3
methyl 5-(2-hydroxyphenyl)cyclopentene-1-carboxylate
—— 2-((4-Chlorobenzyl)oxy)-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide 347880-76-6 C22H19ClN2O4
2-((4-Chlorobenzyl)oxy)-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide
—— 2,4-dibromo-6-[(3-dimethylaminopropylimino)methyl]phenol 1173550-99-6 C12H16Br2N2O
2,4-dibromo-6-[(3-dimethylaminopropylimino)methyl]phenol
—— 2-(4-hydroxy-3-methoxyphenyl)-1,3,4-oxadiazol-5-one 79302-78-6 C9H8N2O4
2-(4-hydroxy-3-methoxyphenyl)-1,3,4-oxadiazol-5-one
—— 2,3-Diamino-4,6-difluoro-phenol 906081-31-0 C6H6F2N2O
2,3-Diamino-4,6-difluoro-phenol
—— Phenol, 2,6-bis(1,1-dimethylethyl)-4-[(3-methylbutyl)oxy]- 143485-09-0 C19H32O2
Phenol, 2,6-bis(1,1-dimethylethyl)-4-[(3-methylbutyl)oxy]-
—— 1-(4-Hydroxyphenyl)-2-hexen 22184-03-8 C12H16O
1-(4-Hydroxyphenyl)-2-hexen
—— N-[(2-hydroxy-5-nitrophenyl)methylideneamino]-N'-phenyl-1,3-benzothiazole-2-carboximidamide 7038-36-0 C21H15N5O3S
N-[(2-hydroxy-5-nitrophenyl)methylideneamino]-N'-phenyl-1,3-benzothiazole-2-carboximidamide
—— 2-((N-benzylpyrid-2-ylmethylamino)methyl)-4-nitrophenol 1346254-11-2 C20H19N3O3
2-((N-benzylpyrid-2-ylmethylamino)methyl)-4-nitrophenol
—— 2-(2-Methoxy-phenoxy)-1-(3-methoxy-4-hydroxy-phenyl)-ethan-sulfonsaeure 29340-53-2 C16H18O7S
2-(2-Methoxy-phenoxy)-1-(3-methoxy-4-hydroxy-phenyl)-ethan-sulfonsaeure
—— {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile 91827-16-6 C14H17NO4
{2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile
—— 2-(Azepane-1-carbonyl)-4,5-dihydroxy-3-nitrobenzonitrile 1202893-31-9 C14H15N3O5
2-(Azepane-1-carbonyl)-4,5-dihydroxy-3-nitrobenzonitrile
—— N-(2-Hydroxy-5-nitrophenyl)-aconamid 24734-11-0 C11H8N2O6
N-(2-Hydroxy-5-nitrophenyl)-aconamid
—— (S)-N1-(9-(3-((S)-2-amino-5-guanidinopentanamido)propylamino)nonyl)-2-(2-(2,4-dihydroxyphenyl)acetamido)succinamide 1209469-05-5 C30H53N9O6
(S)-N1-(9-(3-((S)-2-amino-5-guanidinopentanamido)propylamino)nonyl)-2-(2-(2,4-dihydroxyphenyl)acetamido)succinamide
—— 2-{2-[(6-Oxocyclohexa-2,4-dien-1-ylidene)methyl]hydrazinylidene}propanoic acid 193552-76-0 C10H10N2O3
2-{2-[(6-Oxocyclohexa-2,4-dien-1-ylidene)methyl]hydrazinylidene}propanoic acid
—— N<sup>1</sup>-4-chlorobenzylidene-N<sup>2</sup>-[3-(3-hydroxy-4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine 1380075-06-8 C23H18ClN3O4S
N<sup>1</sup>-4-chlorobenzylidene-N<sup>2</sup>-[3-(3-hydroxy-4-methoxyphenyl)-4-(2,5-dihydroxyphenyl)-1,3-thiazol-2-ylidene]hydrazine
—— 4-(1-Ethyl-hexyl)-2,6-dinitro-phenol; compound with piperidine 13572-70-8 C5H11N*C14H20N2O5
4-(1-Ethyl-hexyl)-2,6-dinitro-phenol; compound with piperidine
—— 4,4'-(1E,1'E)-2,2'-(1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl)bis(2-methoxy-6-(3-methylbut-2-enyl)phenol) 1616504-29-0 C31H36N2O4
4,4'-(1E,1'E)-2,2'-(1H-pyrazole-3,5-diyl)bis(ethene-2,1-diyl)bis(2-methoxy-6-(3-methylbut-2-enyl)phenol)
—— N-(3-Amino-propyl)-2,5-dihydroxy-anilin 91054-81-8 C9H14N2O2
N-(3-Amino-propyl)-2,5-dihydroxy-anilin
—— 17291-69-9 C14H9Br2ClN2O3
—— N-(5-Chloro-2,4-dihydroxy-benzyl)-acrylamide 13579-39-0 C10H10ClNO3
N-(5-Chloro-2,4-dihydroxy-benzyl)-acrylamide
—— β-(4-Hydroxy)phenylethyl nonanoate 137422-38-9 C17H26O3
β-(4-Hydroxy)phenylethyl nonanoate
—— 2-(2-(2-hydroxy-4-nitrobenzylidene)hydrazineyl)-6-methylpyrimidin-4(3H)-one 91843-80-0 C12H11N5O4
2-(2-(2-hydroxy-4-nitrobenzylidene)hydrazineyl)-6-methylpyrimidin-4(3H)-one
—— 6-(3,5-dihydroxyphenoxy)-hexanoic acid ethyl ester 1335102-10-7 C14H20O5
6-(3,5-dihydroxyphenoxy)-hexanoic acid ethyl ester
—— 5-(4-aminocyclohexyl)amino-7-(2,5-dihydroxy-4-methoxybenzyl)amino-3-isopropylpyrazolo[4,3-d]pyrimidine 607727-39-9 C22H31N7O3
5-(4-aminocyclohexyl)amino-7-(2,5-dihydroxy-4-methoxybenzyl)amino-3-isopropylpyrazolo[4,3-d]pyrimidine
—— [3,6-Dihydroxy-2-(1-methoxy-vinyl)-phenyl]-phosphonic acid dimethyl ester 36047-22-0 C11H15O6P
[3,6-Dihydroxy-2-(1-methoxy-vinyl)-phenyl]-phosphonic acid dimethyl ester
—— (Z)-5-(4-hydroxy-3-methoxyphenyl)pent-4-enal 1654741-61-3 C12H14O3
(Z)-5-(4-hydroxy-3-methoxyphenyl)pent-4-enal
—— 2,2'-((4,6-dihydroxy-1,3-phenylene)bis(ethan-1-yl-1-ylidene))bis(hydrazine-1-carboximidamide) hydrochloride 87533-42-4 C12H18N8O2*2ClH
2,2'-((4,6-dihydroxy-1,3-phenylene)bis(ethan-1-yl-1-ylidene))bis(hydrazine-1-carboximidamide) hydrochloride
—— 1402687-49-3 C12H16Cl2CuO5
—— 2-[[5-[[2-[(2-Hydroxy-5-nitrophenyl)methylideneamino]-1,3-thiazol-5-yl]methyl]-1,3-thiazol-2-yl]iminomethyl]-4-nitrophenol 1079355-07-9 C21H14N6O6S2
2-[[5-[[2-[(2-Hydroxy-5-nitrophenyl)methylideneamino]-1,3-thiazol-5-yl]methyl]-1,3-thiazol-2-yl]iminomethyl]-4-nitrophenol
—— 2,6-Ditert-butyl-4-[(3-pyridin-4-yloxypropylamino)methyl]phenol 1148000-10-5 C23H34N2O2
2,6-Ditert-butyl-4-[(3-pyridin-4-yloxypropylamino)methyl]phenol
—— 2-(5-aminotetrazol-2-yl)-N-[(E)-(4-hydroxyphenyl)methylideneamino]acetamide 347863-60-9 C10H11N7O2
2-(5-aminotetrazol-2-yl)-N-[(E)-(4-hydroxyphenyl)methylideneamino]acetamide
—— [(3-Bromo-4-hydroxy-5-methoxy-phenyl)-hydroxy-methyl]-phosphonic acid diisopropyl ester 38707-01-6 C14H22BrO6P
[(3-Bromo-4-hydroxy-5-methoxy-phenyl)-hydroxy-methyl]-phosphonic acid diisopropyl ester
—— 2-cyclopentylphenyl 3-(4-hydroxy-3-methoxybenzylcarbamoyl)-azetidine-1-carboxylate 1193988-37-2 C24H28N2O5
2-cyclopentylphenyl 3-(4-hydroxy-3-methoxybenzylcarbamoyl)-azetidine-1-carboxylate
—— 5,2-Bromhydroxy-benzoesaeure-5-nitrosalicyliden-hydrazon 41377-57-5 C14H10BrN3O5
5,2-Bromhydroxy-benzoesaeure-5-nitrosalicyliden-hydrazon