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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-nitro-4-(n-propyl)-aminophenol 92952-82-4 C9H12N2O3
3-nitro-4-(n-propyl)-aminophenol
—— (9Z,12Z)-1-(2-(3,4-dihydroxyphenyl)ethoxy)-octadeca-9,12-diene 1354701-20-4 C26H42O3
(9Z,12Z)-1-(2-(3,4-dihydroxyphenyl)ethoxy)-octadeca-9,12-diene
—— 2-<3',4'-bis(benzyloxy)phenyl>-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide 138645-00-8 C31H31NO5
2-<3',4'-bis(benzyloxy)phenyl>-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide
—— 5-Hydroxymethyl-homovanillinsaeure 37941-99-4 C10H12O5
5-Hydroxymethyl-homovanillinsaeure
—— 5-bromo-salicylidene-4-bromoaniline 93186-78-8 C13H9Br2NO
5-bromo-salicylidene-4-bromoaniline
—— 3,4-dihydroxyphenylacetic acid-4-hydroxyphenethyl ester 1428533-03-2 C16H16O5
3,4-dihydroxyphenylacetic acid-4-hydroxyphenethyl ester
—— 3-(4-hydroxyphenyl)-1-cyclopentylpropan-1-one 625446-00-6 C14H18O2
3-(4-hydroxyphenyl)-1-cyclopentylpropan-1-one
—— α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide 365572-40-3 C18H20BrNO4
α-[2-bromo-5-hydroxy-4-methoxyphenyl]-4-hydroxybenzenepentanamide
—— N-dodecyl-3-(4-hydroxyphenyl)propanamide 914491-21-7 C21H35NO2
N-dodecyl-3-(4-hydroxyphenyl)propanamide
—— 4-(3-bromopropyl)phenol 52273-55-9 C9H11BrO
4-(3-bromopropyl)phenol
—— 2,5-dihydroxy-4-methoxy-benzaldehyde 29865-97-2 C8H8O4
2,5-dihydroxy-4-methoxy-benzaldehyde
—— 3,5-dichloropicric acid 19046-87-8 C6HCl2N3O7
3,5-dichloropicric acid
—— 2-(4-hydroxy-3-methoxyphenyl)-N-nonylpropanamide 1391847-91-8 C19H31NO3
2-(4-hydroxy-3-methoxyphenyl)-N-nonylpropanamide
—— 1,3,5-tris(2-furyl)-1-phenol 1221128-69-3 C18H12O4
1,3,5-tris(2-furyl)-1-phenol
—— 3,5-dichloro-2-nitrophenol 74672-02-9 C6H3Cl2NO3
3,5-dichloro-2-nitrophenol
—— N-[(4-tert-butylphenyl)methyl]-2-(4-hydroxy-3-methoxyphenyl)propanamide 1391848-04-6 C21H27NO3
N-[(4-tert-butylphenyl)methyl]-2-(4-hydroxy-3-methoxyphenyl)propanamide
—— bis-(3,5-dibromo-2-hydroxyphenyl)disulfide 61268-38-0 C12H6Br4O2S2
bis-(3,5-dibromo-2-hydroxyphenyl)disulfide
—— 2,5,6-Trideutero-homovanillinsaeure 68408-02-6 C9H10O4
2,5,6-Trideutero-homovanillinsaeure
—— 3-Chloro-4,6-dimethyl-benzene-1,2-diol 57341-96-5 C8H9ClO2
3-Chloro-4,6-dimethyl-benzene-1,2-diol
—— (4'-hydroxy-3'-methoxyphenyl)-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide 138645-09-7 C18H21NO5
(4'-hydroxy-3'-methoxyphenyl)-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide
—— N-[3-(3,4-dimethylphenyl)propyl]-2-(4-hydroxy-3-methoxyphenyl)propanamide 1391847-92-9 C21H27NO3
N-[3-(3,4-dimethylphenyl)propyl]-2-(4-hydroxy-3-methoxyphenyl)propanamide
—— 2-(4-hydroxy-3-methoxyphenyl)-N-octylpropanamide 1391847-90-7 C18H29NO3
2-(4-hydroxy-3-methoxyphenyl)-N-octylpropanamide
—— N-[3-pivaloyloxy-2-(4-t-butylbenzyl)propyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide 289903-41-9 C28H39NO5
N-[3-pivaloyloxy-2-(4-t-butylbenzyl)propyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— N-(4-t-butylbenzyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide 1258845-91-8 C20H25NO3
N-(4-t-butylbenzyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— Tyrosol homovanillate 1428533-05-4 C17H18O5
Tyrosol homovanillate
—— 2,4,6-tris(2-thienyl)-1-phenol 1221128-66-0 C18H12OS3
2,4,6-tris(2-thienyl)-1-phenol
—— 2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide 1395084-66-8 C18H21NO4
2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
—— Benzeneacetamide, N-9-decenyl-4-hydroxy-3-methoxy- 107512-61-8 C19H29NO3
Benzeneacetamide, N-9-decenyl-4-hydroxy-3-methoxy-
—— ((4-hydroxy-3-methoxyphenyl)acetyl)pyrrolidine 131656-82-1 C13H17NO3
((4-hydroxy-3-methoxyphenyl)acetyl)pyrrolidine
—— N-(4-butyl-3-cyclohexenyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide 913746-57-3 C19H27NO3
N-(4-butyl-3-cyclohexenyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— N-Octylhomovanillamide 58418-73-8 C17H27NO3
N-Octylhomovanillamide
—— N-benzyloxy-N-octyl-2-(4-hydroxy-3-methoxyphenyl)acetamide 1400943-51-2 C24H33NO4
N-benzyloxy-N-octyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— Benzeneacetamide, 4-hydroxy-3-methoxy-N-nonyl- 107512-63-0 C18H29NO3
Benzeneacetamide, 4-hydroxy-3-methoxy-N-nonyl-
—— KR-25003 142333-36-6 C20H25NO3
KR-25003
—— 2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid 2989-10-8 C9H10O5
2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid
—— Benzeneacetamide, N-cyclooctyl-4-hydroxy-3-methoxy- 107512-66-3 C17H25NO3
Benzeneacetamide, N-cyclooctyl-4-hydroxy-3-methoxy-
—— N-benzyloxy-N-heptyl-2-(4-hydroxy-3-methoxyphenyl)acetamide 1400943-49-8 C23H31NO4
N-benzyloxy-N-heptyl-2-(4-hydroxy-3-methoxyphenyl)acetamide
—— 2-(4-Hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)ethan-1-one 53283-49-1 C14H19NO3
2-(4-Hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)ethan-1-one
—— N-benzyl-4-hydroxy-3-methoxyphenylacetamide 391609-30-6 C16H17NO3
N-benzyl-4-hydroxy-3-methoxyphenylacetamide
—— 3-methoxy-4-hydroxy mandelic acid 13244-77-4 C9H10O5
3-methoxy-4-hydroxy mandelic acid
—— vanillyl-methylamine 42973-53-5 C9H13NO2
vanillyl-methylamine
—— 2-chloro-4-methoxy-6-prop-2-enylphenol 359844-32-9 C10H11ClO2
2-chloro-4-methoxy-6-prop-2-enylphenol
—— 4-bromo-2,3,5,6-tetrachlorophenol 4091-48-9 C6HBrCl4O
4-bromo-2,3,5,6-tetrachlorophenol
—— 3-bromo-5-fluorobenzene-1,2-diol 913629-79-5 C6H4BrFO2
3-bromo-5-fluorobenzene-1,2-diol
—— 4,6-dimercaptoresorcine 120256-66-8 C6H6O2S2
4,6-dimercaptoresorcine
—— 4-Bromo-2-phenylmethoxybenzene-1,3-diol 765915-41-1 C13H11BrO3
4-Bromo-2-phenylmethoxybenzene-1,3-diol
—— tert-butyl N-[8-[3-(4-hydroxyphenyl)propanoylamino]octyl]carbamate 1262963-03-0 C22H36N2O4
tert-butyl N-[8-[3-(4-hydroxyphenyl)propanoylamino]octyl]carbamate
—— (E)-2-((benzylimino)methyl)-4-nitrophenol 53848-16-1 C14H12N2O3
(E)-2-((benzylimino)methyl)-4-nitrophenol
—— 3,5-Dimethyl-2-(3-methyl-but-2-enyl)-phenol 129698-01-7 C13H18O
3,5-Dimethyl-2-(3-methyl-but-2-enyl)-phenol
—— Carbonic acid (2S,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-4,5-dihydroxy-6-{[3-(4-hydroxy-phenyl)-propionylamino]-methyl}-tetrahydro-pyran-2-yl ester tert-butyl ester 910055-71-9 C25H38N2O10
Carbonic acid (2S,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-4,5-dihydroxy-6-{[3-(4-hydroxy-phenyl)-propionylamino]-methyl}-tetrahydro-pyran-2-yl ester tert-butyl ester