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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
—— 3-Methylsulfanylmethyl-phenol 35377-64-1 C8H10OS
3-Methylsulfanylmethyl-phenol
—— 1414652-40-6 C34H50O8
—— acetic acid-(5-hydroxy-2,4-dinitro-anilide) 90004-42-5 C8H7N3O6
acetic acid-(5-hydroxy-2,4-dinitro-anilide)
—— (E)-3-(3-(3-hydroxy-4-methoxybenzylidene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine 1233225-27-8 C18H18N2O2
(E)-3-(3-(3-hydroxy-4-methoxybenzylidene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine
—— (3-Chloro-2-hydroxy-phenyl)-furan-2-yl-methanone oxime 97034-82-7 C11H8ClNO3
(3-Chloro-2-hydroxy-phenyl)-furan-2-yl-methanone oxime
—— methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate 752259-59-9 C18H21NO4
methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate
—— 4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-2-prop-2-enylphenol 188842-41-3 C14H16N2O2
4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-2-prop-2-enylphenol
—— 5-Methoxymethyl-vanillin 92315-85-0 C10H12O4
5-Methoxymethyl-vanillin
—— 6,6'-((disulfanediylbis(4-hydroxy-2,1-phenylene))bis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine 6-sulfide) 1402141-43-8 C36H24O6P2S4
6,6'-((disulfanediylbis(4-hydroxy-2,1-phenylene))bis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine 6-sulfide)
—— 2-(3,3-difluoro-2-methyloxiranyl)phenol 1175701-79-7 C9H8F2O2
2-(3,3-difluoro-2-methyloxiranyl)phenol
—— bis(isonicotinamidosalicylaldimine)tetrabromothorium(IV) 155642-06-1 C26H22Br4N6O4Th
bis(isonicotinamidosalicylaldimine)tetrabromothorium(IV)
—— heptyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide 111385-49-0 Br*C17H30NO2
heptyl-[2-(4-hydroxy-phenoxy)-ethyl]-dimethyl-ammonium; bromide
—— 2,2'-[(1-prop-2-enylethane-1,2-diyl)bis(nitrilomethylidyne)]diphenol 150374-55-3 C19H20N2O2
2,2'-[(1-prop-2-enylethane-1,2-diyl)bis(nitrilomethylidyne)]diphenol
—— 5,11,17,23-tetra-tert-butyl-26,28-bis((dimethyl(thiocarbamoyl))oxy)calix<4>arene-25,27-diol 297749-65-6 C50H66N2O4S2
5,11,17,23-tetra-tert-butyl-26,28-bis((dimethyl(thiocarbamoyl))oxy)calix<4>arene-25,27-diol
—— Methyl 3-(3-fluoro-2,4-dihydroxyphenyl)propanoate 909906-21-4 C10H11FO4
Methyl 3-(3-fluoro-2,4-dihydroxyphenyl)propanoate
—— 5-(2-cyclohexyl-2-hydroxyethyl)-5H-imidazo[5,1-α]isoindol-9-ol 1402836-88-7 C18H22N2O2
5-(2-cyclohexyl-2-hydroxyethyl)-5H-imidazo[5,1-α]isoindol-9-ol
—— tyrosol trifluoroacetate 1056355-35-1 C10H9F3O3
tyrosol trifluoroacetate
—— benzyl hydrogen (5-chloro-2-hydroxybenzylidene)carbonohydrazonodithioate 85429-62-5 C15H13ClN2OS2
benzyl hydrogen (5-chloro-2-hydroxybenzylidene)carbonohydrazonodithioate
—— 3-(2,4-dihydroxybenzyl)-4-hydroxy-N-pentylbutanamide 1515406-03-7 C16H25NO4
3-(2,4-dihydroxybenzyl)-4-hydroxy-N-pentylbutanamide
—— 3-((1S,6R,10R)-10-Amino-bicyclo[4.3.1]dec-1-yl)-phenol; hydrobromide 75210-08-1 BrH*C16H23NO
3-((1S,6R,10R)-10-Amino-bicyclo[4.3.1]dec-1-yl)-phenol; hydrobromide
—— 5-(5-bromo-4-fluoro-2-hydroxyphenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione 372120-07-5 C17H13BrFNO5
5-(5-bromo-4-fluoro-2-hydroxyphenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione
—— 4-(5-chlorobenzo[d]thiazol-2-yl)-2,6-dimethoxyphenol 1393371-50-0 C15H12ClNO3S
4-(5-chlorobenzo[d]thiazol-2-yl)-2,6-dimethoxyphenol
—— (-)-(R,R)-[N,N'-bis-(2'-hydroxybenzylidene)]-1,2-diaminocyclopropane 693274-26-9 C17H16N2O2
(-)-(R,R)-[N,N'-bis-(2'-hydroxybenzylidene)]-1,2-diaminocyclopropane
—— 4-[[[1-[(4-Chlorophenyl)methyl]benzimidazol-2-yl]amino]methyl]-2-methoxy-6-(morpholin-4-ylmethyl)phenol 144836-43-1 C27H29ClN4O3
4-[[[1-[(4-Chlorophenyl)methyl]benzimidazol-2-yl]amino]methyl]-2-methoxy-6-(morpholin-4-ylmethyl)phenol
—— 6-Hydroxy-3,5-dimethyl-phthalsaeure-dinitril 90842-11-8 C10H8N2O
6-Hydroxy-3,5-dimethyl-phthalsaeure-dinitril
—— (E)-methyl 2-(2-hydroxy-4-methylphenyl)pent-2-enoate 1595071-44-5 C13H16O3
(E)-methyl 2-(2-hydroxy-4-methylphenyl)pent-2-enoate
—— 2-(bis(1-methylbenzimidazol-2-yl)aminomethyl)-4-nitrophenol 402506-58-5 C25H24N6O3
2-(bis(1-methylbenzimidazol-2-yl)aminomethyl)-4-nitrophenol
—— 5-salicyclidene-4-thioxo-2-imidazolidinone 52800-61-0 C10H8N2O2S
5-salicyclidene-4-thioxo-2-imidazolidinone
—— 2-((2-methyl-2-(pyridin-2-yl)-3-(pyridin-2-ylmethyleneamino)propylimino)methyl)phenol 1415260-30-8 C22H22N4O
2-((2-methyl-2-(pyridin-2-yl)-3-(pyridin-2-ylmethyleneamino)propylimino)methyl)phenol
—— 4,4-dimethylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate 1193987-99-3 C23H34N2O5
4,4-dimethylcyclohexyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate
—— 2-methoxy-5-(methoxycarbonimidoyl)phenol 1178463-92-7 C9H11NO3
2-methoxy-5-(methoxycarbonimidoyl)phenol
—— 4-Cyclopentylmethyl-phenol 129125-84-4 C12H16O
4-Cyclopentylmethyl-phenol
—— (E,E)-2-(phenylethylaminocarbonyl)-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile 368836-82-2 C22H22N2O4
(E,E)-2-(phenylethylaminocarbonyl)-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile
—— 3-Hydroxy-4-nitro-benzyloxyamin 49558-20-5 C7H8N2O4
3-Hydroxy-4-nitro-benzyloxyamin
—— 6-Methylmercaptomethyl-kreosol 18738-39-1 C10H14O2S
6-Methylmercaptomethyl-kreosol
—— 2,2'-[(2,2-dimethyl-1,3-propanediyl)bis(nitriloethylidyne)]bis[phenol] 150164-10-6 C21H26N2O2
2,2'-[(2,2-dimethyl-1,3-propanediyl)bis(nitriloethylidyne)]bis[phenol]
—— 4-hex-5-yn-2-ylphenol 1245947-65-2 C12H14O
4-hex-5-yn-2-ylphenol
—— N-[1-(5-bromo-2-hydroxyphenyl)ethylideneamino]benzamide 1235578-12-7 C15H13BrN2O2
N-[1-(5-bromo-2-hydroxyphenyl)ethylideneamino]benzamide
—— N<sup>1</sup>-4-chlorobenzylidene-N<sup>2</sup>-[3-(4-hydroxy-3-methoxyphenyl)-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazine 1380075-18-2 C23H16ClN3O4S
N<sup>1</sup>-4-chlorobenzylidene-N<sup>2</sup>-[3-(4-hydroxy-3-methoxyphenyl)-4-(1,4-benzoquinon-2-yl)-1,3-thiazol-2-ylidene]hydrazine
—— 5-[(5R)-1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl]-2-methoxyphenol 1013655-58-7 C13H15NO4
5-[(5R)-1,7-dioxa-2-azaspiro[4.4]non-2-en-3-yl]-2-methoxyphenol
—— 2,4,5-Triiodophenol 59697-17-5 C6H3I3O
2,4,5-Triiodophenol
—— 6-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]hexanamide 1067970-29-9 C14H21NO3
6-hydroxy-N-[2-(4-hydroxyphenyl)ethyl]hexanamide
—— 2-<2-hydroxy-1-(isopropylthio)ethyl>-4-nitrophenol 121045-24-7 C11H15NO4S
2-<2-hydroxy-1-(isopropylthio)ethyl>-4-nitrophenol
—— 3-[[4-[[4-[(2,3-Dihydroxyphenyl)methylideneamino]phenyl]disulfanyl]phenyl]iminomethyl]benzene-1,2-diol 674285-06-4 C26H20N2O4S2
3-[[4-[[4-[(2,3-Dihydroxyphenyl)methylideneamino]phenyl]disulfanyl]phenyl]iminomethyl]benzene-1,2-diol
—— 57299-29-3 C9H9CuNO5
—— 2-(4-hydroxyphenyl)ethyl 2-[(1S,2E,3S,4R)-2-ethylidene-3,4-dihydroxycyclopentyl]acetate 944340-53-8 C17H22O5
2-(4-hydroxyphenyl)ethyl 2-[(1S,2E,3S,4R)-2-ethylidene-3,4-dihydroxycyclopentyl]acetate
—— 2-[(2-amino-phenylimino)-methyl]-4-bromo-phenol 51800-88-5 C13H11BrN2O
2-[(2-amino-phenylimino)-methyl]-4-bromo-phenol
—— 3-Ethenyl-6-nitro-1,2-benzenediol 72915-13-0 C8H7NO4
3-Ethenyl-6-nitro-1,2-benzenediol
—— 2-(phenylimino-methyl)-hydroquinone 126006-60-8 C13H11NO2
2-(phenylimino-methyl)-hydroquinone
—— 3-Iod-synephrin 3689-34-7 C9H12INO2
3-Iod-synephrin