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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-Phenyl-3-(4-chlor-2-hydroxy-5-methyl-phenyl)-isooxazol 19743-15-8 C16H12ClNO2
5-Phenyl-3-(4-chlor-2-hydroxy-5-methyl-phenyl)-isooxazol
—— 1398573-41-5 C28H46BrNO4
—— 2,4,6-tribromo-5-methoxyresorcinol 121869-54-3 C7H5Br3O3
2,4,6-tribromo-5-methoxyresorcinol
—— 4-Hydroxy-5-nitro-benzene-1,3-disulfonic acid bis-dipropylamide 31972-16-4 C18H31N3O7S2
4-Hydroxy-5-nitro-benzene-1,3-disulfonic acid bis-dipropylamide
—— N-(1'-hydroxy-2'-butyl)-2-hydroxyacetophenoneimine 42592-34-7 C12H17NO2
N-(1'-hydroxy-2'-butyl)-2-hydroxyacetophenoneimine
—— 1050300-28-1 C96H162N20O12
—— 4-hydroxybenzaldehyde-N-dodecylimine 20172-65-0 C19H31NO
4-hydroxybenzaldehyde-N-dodecylimine
—— Glyoxal-bis(2-hydroxy-5-nitro-anil) 1433-78-9 C14H10N4O6
Glyoxal-bis(2-hydroxy-5-nitro-anil)
—— [(4-Hydroxy-benzimidoyl)-aminooxy]-acetic acid ethyl ester 63409-59-6 C11H14N2O4
[(4-Hydroxy-benzimidoyl)-aminooxy]-acetic acid ethyl ester
—— 4-[5-(3-hydroxy-phenyl)-oxazolidin-2-yl]-benzene-1,3-diol 57083-80-4 C15H15NO4
4-[5-(3-hydroxy-phenyl)-oxazolidin-2-yl]-benzene-1,3-diol
—— 5-(3-Fluorophenyl)-2-(3-(3-(5-hydroxypyridin-2-yl)-1,2,4-oxadiazol-5-yl)propanamido)cyclohex-1-enecarboxylic acid 946113-67-3 C23H21FN4O5
5-(3-Fluorophenyl)-2-(3-(3-(5-hydroxypyridin-2-yl)-1,2,4-oxadiazol-5-yl)propanamido)cyclohex-1-enecarboxylic acid
—— 4,4'-(((2-hydroxy-5-methyl-1,3-phenylene)bis(methaneylylidene))bis(azaneylylidene))bis(1,2,4-triazolidine-3,5-dithione) 500759-28-4 C13H12N8OS4
4,4'-(((2-hydroxy-5-methyl-1,3-phenylene)bis(methaneylylidene))bis(azaneylylidene))bis(1,2,4-triazolidine-3,5-dithione)
—— 4789-93-9 C10H9Br2NO3
—— [(5-Bromo-2-hydroxy-phenyl)-hydroxy-methyl]-phosphonic acid dipropyl ester 36971-34-3 C13H20BrO5P
[(5-Bromo-2-hydroxy-phenyl)-hydroxy-methyl]-phosphonic acid dipropyl ester
—— 4-(4-Hydroxy-3-methoxy-benzyliden)-6-phenyl-3,4-dihydro-<1,3,5>oxadiazin-2-on 14326-95-5 C17H14N2O4
4-(4-Hydroxy-3-methoxy-benzyliden)-6-phenyl-3,4-dihydro-<1,3,5>oxadiazin-2-on
—— N-(5-Chlorsalicyliden)-D-cycloserin 3970-03-4 C10H9ClN2O3
N-(5-Chlorsalicyliden)-D-cycloserin
—— (R)-2-<(sec-Butylamino)methyl>-4-nitrophenol 1071208-73-5 C11H16N2O3
(R)-2-<(sec-Butylamino)methyl>-4-nitrophenol
—— 5-methoxy-2-(1-hydroxyhexyl)-1,4-benzenediol 108214-08-0 C13H20O4
5-methoxy-2-(1-hydroxyhexyl)-1,4-benzenediol
—— (R)-(4-Hydroxy-phenyl)-((R)-1-methyl-butoxy)-acetonitrile 133412-41-6 C13H17NO2
(R)-(4-Hydroxy-phenyl)-((R)-1-methyl-butoxy)-acetonitrile
—— 2-amino-4-chloro-5-ethylphenol 32748-97-3 C8H10ClNO
2-amino-4-chloro-5-ethylphenol
—— 2-(5-Phenyl-1-pyridin-2-yl-4,5-dihydro-1H-pyrazol-3-yl)-phenol 474766-58-0 C20H17N3O
2-(5-Phenyl-1-pyridin-2-yl-4,5-dihydro-1H-pyrazol-3-yl)-phenol
—— N-(5-Chloro-2-hydroxy-3-nitro-benzyl)-acrylamide 13579-34-5 C10H9ClN2O4
N-(5-Chloro-2-hydroxy-3-nitro-benzyl)-acrylamide
—— [Ag(15-hydroxybenzo-15-crown-5)(acetonitrile)](perchlorate) 1262034-65-0 C16H23AgNO6*ClO4
[Ag(15-hydroxybenzo-15-crown-5)(acetonitrile)](perchlorate)
—— 2,2,2-trifluoro-N-[2-(2-hydroxy-4,5-dimethoxyphenyl)ethyl]acetamide 141939-59-5 C12H14F3NO4
2,2,2-trifluoro-N-[2-(2-hydroxy-4,5-dimethoxyphenyl)ethyl]acetamide
—— 5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(4-chloro-2,5-dimethoxyphenyl)-1,3-diazinane-2,4,6-trione 425419-94-9 C20H16BrClN2O7
5-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]-1-(4-chloro-2,5-dimethoxyphenyl)-1,3-diazinane-2,4,6-trione
—— 2,6-Diheptyl-phenol 116374-98-2 C20H34O
2,6-Diheptyl-phenol
—— 2-Hydroxy-5-nitro-3,6-dimethyl-benzylchlorid 17959-07-8 C9H10ClNO3
2-Hydroxy-5-nitro-3,6-dimethyl-benzylchlorid
—— 3-amino-6-bromo-2,4-dinitro-phenol 858013-98-6 C6H4BrN3O5
3-amino-6-bromo-2,4-dinitro-phenol
—— 2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide 622347-39-1 C21H33NO5
2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide
—— 4-[(4aR,8aS)-2-amino-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-3-fluorophenol 1425947-74-5 C13H15FN2O2S
4-[(4aR,8aS)-2-amino-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl]-3-fluorophenol
—— 6-Chlor-3,5-dihydroxy-o-xylol 17554-89-1 C8H9ClO2
6-Chlor-3,5-dihydroxy-o-xylol
—— (5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-36-6 C16H18N2O3S
(5Z)-5-[(2-hydroxy-5-methoxyphenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 5-{1-hydroxy-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-ethyl}-benzene-1,3-diol 52536-67-1 C14H22N2O4
5-{1-hydroxy-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-ethyl}-benzene-1,3-diol
—— 4-[1-hydroxy-2-(4-methyl-piperazin-1-yl)-ethyl]-benzene-1,2-diol 15534-24-4 C13H20N2O3
4-[1-hydroxy-2-(4-methyl-piperazin-1-yl)-ethyl]-benzene-1,2-diol
—— 1385126-55-5 C48H50N9O6P3
—— 4,4'-(adamantan-1-ylmethylene)diphenol 1227162-18-6 C23H26O2
4,4'-(adamantan-1-ylmethylene)diphenol
—— 39151-47-8 C6H5N2O*F6P
—— 3-Phenyl-5-methyl-4-isoxazoyl-<4-hydroxybenzylidenhydrazid> 18336-82-8 C18H15N3O3
3-Phenyl-5-methyl-4-isoxazoyl-<4-hydroxybenzylidenhydrazid>
—— 1,1,1-tris[(4-hydroxy-3-nitrophenyl)acetamidomethyl]methylamine 1345700-43-7 C28H29N7O12
1,1,1-tris[(4-hydroxy-3-nitrophenyl)acetamidomethyl]methylamine
—— 2,6-Dimethyl-4-((E)-2-nitro-propenyl)-phenol 53205-17-7 C11H13NO3
2,6-Dimethyl-4-((E)-2-nitro-propenyl)-phenol
—— 1-(2-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)ethyl)pyrrolidine-2,5-dione 1187947-91-6 C15H15FN2O4
1-(2-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)ethyl)pyrrolidine-2,5-dione
—— 2-[4-[3-(methylamino)-1-phenylpropoxy]phenyl]ethanol hydrochloride 1615654-07-3 C18H23NO2*ClH
2-[4-[3-(methylamino)-1-phenylpropoxy]phenyl]ethanol hydrochloride
—— (S)-5-(1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methoxyphenol 1044497-22-4 C21H19N5O2
(S)-5-(1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methoxyphenol
—— 1-<2-Methoxy-phenyl>-2-acetylmercapto-2-<3-Methoxy-4-hydroxy-phenyl>-ethan 5288-88-0 C18H20O5S
1-<2-Methoxy-phenyl>-2-acetylmercapto-2-<3-Methoxy-4-hydroxy-phenyl>-ethan
—— Acetic acid 4-[4-(4-acetoxy-3-methoxy-phenyl)-1,4-bis-methoxysulfonyl-2-methoxysulfonylmethyl-butyl]-2-methoxy-phenyl ester 38209-38-0 C26H34O15S3
Acetic acid 4-[4-(4-acetoxy-3-methoxy-phenyl)-1,4-bis-methoxysulfonyl-2-methoxysulfonylmethyl-butyl]-2-methoxy-phenyl ester
—— 1-<3,5,6-Trichlor-2-hydroxy-phenyl>-3-methyl-Δ<sup>2</sup>-pyrazolon-(5) 23280-87-7 C10H7Cl3N2O2
1-<3,5,6-Trichlor-2-hydroxy-phenyl>-3-methyl-Δ<sup>2</sup>-pyrazolon-(5)
—— 1430733-06-4 C34H50N9O14PS
—— (2-hydroxybenzyl-2-tetrahydrofurylmethyl)imine 473717-40-7 C12H15NO2
(2-hydroxybenzyl-2-tetrahydrofurylmethyl)imine
—— (E)-2-((1-hydroxybutan-2-ylimino)methyl)−6-methoxyphenol 1255530-14-3 C12H17NO3
(E)-2-((1-hydroxybutan-2-ylimino)methyl)−6-methoxyphenol
—— 11-Hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-undeca-1,9-diyne 106853-34-3 C18H22O3
11-Hydroxy-1-(4'-hydroxy-3'-methoxyphenyl)-undeca-1,9-diyne