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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
—— 2-amino-N-(3,4-dihydroxyphenethyl)acetamide 46458-11-1 C10H14N2O3
2-amino-N-(3,4-dihydroxyphenethyl)acetamide
—— 1,11-bis(salicylaldimine)-3,6,9-trithiaundecane 1334119-81-1 C22H28N2O2S3
1,11-bis(salicylaldimine)-3,6,9-trithiaundecane
—— N,N'-bis(4-fluorosalicylidene)-1,12-dodecanediamine 1334545-38-8 C26H34F2N2O2
N,N'-bis(4-fluorosalicylidene)-1,12-dodecanediamine
—— N-methyl-p-tert-butyl-homoazacalix[4]arene 651014-16-3 C46H61NO4
N-methyl-p-tert-butyl-homoazacalix[4]arene
—— 2-[(E)-4-(2-Hydroxy-3-methyl-phenyl)-but-2-enyl]-malonic acid diethyl ester 86726-11-6 C18H24O5
2-[(E)-4-(2-Hydroxy-3-methyl-phenyl)-but-2-enyl]-malonic acid diethyl ester
—— trans-4,5-bis(2-hydroxyphenyl)-2-methyl-1,3-dioxolane 124483-12-1 C16H16O4
trans-4,5-bis(2-hydroxyphenyl)-2-methyl-1,3-dioxolane
—— 2-methoxy-5-[2-(7-methoxy-9,9-dimethyl-2,3-dihydro-9<i>H</i>-thiazolo[3,2-<i>a</i>]indol-9a-yl)-vinyl]-phenol 59334-48-4 C22H25NO3S
2-methoxy-5-[2-(7-methoxy-9,9-dimethyl-2,3-dihydro-9<i>H</i>-thiazolo[3,2-<i>a</i>]indol-9a-yl)-vinyl]-phenol
—— 5-{[4-(2-ethyl-4-methyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino}-2-methoxyphenol 930583-54-3 C17H18N4O2S
5-{[4-(2-ethyl-4-methyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino}-2-methoxyphenol
—— Thiobenz-(4-hydroxyanilid) 21011-42-7 C13H11NOS
Thiobenz-(4-hydroxyanilid)
—— 3-<6-(4-Benzyloxyphenyl)-3-hexyl>-2,4-pentandion 57840-52-5 C17H24O3
3-<6-(4-Benzyloxyphenyl)-3-hexyl>-2,4-pentandion
—— 1-{2-[(2-hydroxy-3-methoxybenzylidene)-hydrazono]-4-methyl-3-phenyl-2,3-dihydrothiazol-5-yl}-ethanone 1136238-78-2 C20H19N3O3S
1-{2-[(2-hydroxy-3-methoxybenzylidene)-hydrazono]-4-methyl-3-phenyl-2,3-dihydrothiazol-5-yl}-ethanone
—— 2,6-dimethoxy-3-(3'-methyl-2'-butenyl)-4-<(dimethylamino)methyl>phenol 127757-25-9 C16H25NO3
2,6-dimethoxy-3-(3'-methyl-2'-butenyl)-4-<(dimethylamino)methyl>phenol
—— 4-Hydroxy-3-methoxy-2-cyan-benzaldehyd 6702-49-4 C9H7NO3
4-Hydroxy-3-methoxy-2-cyan-benzaldehyd
—— Co(3,5-dibenzyloxybenzoyl-2-oxy-4-hydroxybenzaldehyde hydrazone)(CH3COO) 614718-11-5 C30H26CoN2O7
Co(3,5-dibenzyloxybenzoyl-2-oxy-4-hydroxybenzaldehyde hydrazone)(CH3COO)
—— 4-bromo-2-chloro-3-methyl-6-nitro-phenol 861576-56-9 C7H5BrClNO3
4-bromo-2-chloro-3-methyl-6-nitro-phenol
—— 4-hydroxy-3-methoxy-5-(5-methyl-2-furyl)benzonitrile 114106-71-7 C13H11NO3
4-hydroxy-3-methoxy-5-(5-methyl-2-furyl)benzonitrile
—— diethyl 2-chloro-3-(3-chloro-4-hydroxy-5-methoxybenzyl)malonate 86726-59-2 C15H18Cl2O6
diethyl 2-chloro-3-(3-chloro-4-hydroxy-5-methoxybenzyl)malonate
—— 4-Oxy-azoxybenzol 16054-49-2 C12H10N2O2
4-Oxy-azoxybenzol
—— 2-bromo-4-(octyloxy)phenol 851438-36-3 C14H21BrO2
2-bromo-4-(octyloxy)phenol
—— 1390619-66-5 C15H23NO2
—— 3-Ethoxy-2,5-di-tert.-butyl-hydrochinon 2581-92-2 C16H26O3
3-Ethoxy-2,5-di-tert.-butyl-hydrochinon
—— 2-hydroxy-6-methoxy-4-(2-methyloctan-2-yl)benzaldehyde 1399049-47-8 C17H26O3
2-hydroxy-6-methoxy-4-(2-methyloctan-2-yl)benzaldehyde
—— 6-<(benzimidazol-2-yliothio)phenyl-λ<sup>3</sup>-iodanyl>-2,4-dinitrophenolate 100351-31-3 C19H13IN4O5S
6-<(benzimidazol-2-yliothio)phenyl-λ<sup>3</sup>-iodanyl>-2,4-dinitrophenolate
—— 3-n-(1-Cyclohexylmethyl)-octyl-brenzkatechin 21704-28-9 C21H34O2
3-n-(1-Cyclohexylmethyl)-octyl-brenzkatechin
—— 1-(4'-Hydroxy-3'-methoxyphenyl)-2-nitro-hexen 1219-82-5 C13H17NO4
1-(4'-Hydroxy-3'-methoxyphenyl)-2-nitro-hexen
—— 3-(3-hydroxy-benzyl)-pentane-2,4-dione 791809-36-4 C12H14O3
3-(3-hydroxy-benzyl)-pentane-2,4-dione
—— N,N-dibutyl-N'-(2-hydroxyphenyl)formimidamide 1423020-92-1 C15H24N2O
N,N-dibutyl-N'-(2-hydroxyphenyl)formimidamide
—— 2-(5-Nitro-3-chlor-2-hydroxy-phenylhydrazono)-propionsaeure-ethylester 19169-37-0 C11H12ClN3O5
2-(5-Nitro-3-chlor-2-hydroxy-phenylhydrazono)-propionsaeure-ethylester
—— 124218-05-9 C19H27NO2
—— (E)-4-[(5-chloro-2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 1418275-13-4 C13H14ClN5O2S
(E)-4-[(5-chloro-2-hydroxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one
—— 2-fluoro-6-(phenylselenyl)phenol 1350814-97-9 C12H9FOSe
2-fluoro-6-(phenylselenyl)phenol
—— 2-Nitro-benzaldehyd-<2-hydroxy-5-methoxy-benzhydrazon> 2888-04-2 C15H13N3O5
2-Nitro-benzaldehyd-<2-hydroxy-5-methoxy-benzhydrazon>
—— 4-Hexyl-benzene-1,3-diol; compound with piperazine 791-07-1 C4H10N2*C12H18O2
4-Hexyl-benzene-1,3-diol; compound with piperazine
—— 3-Methyl-4-(1-methyl-pentyl)-2-nitro-phenol 4596-03-6 C13H19NO3
3-Methyl-4-(1-methyl-pentyl)-2-nitro-phenol
—— 2-Methoxy-6-[(phenylhydrazinylidene)methyl]phenol 92906-40-6 C14H14N2O2
2-Methoxy-6-[(phenylhydrazinylidene)methyl]phenol
—— 6-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone 39496-71-4 C11H12N2O3
6-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone
—— 2-(2'-hydroxy-5'-chlorophenyl)oxazoline 382594-29-8 C9H8ClNO2
2-(2'-hydroxy-5'-chlorophenyl)oxazoline
—— (1S,2R,3S)-1-(3,4-methylenedioxyphenyl)-3-(4-methoxy-2-hydroxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid 192802-48-5 C27H26O7
(1S,2R,3S)-1-(3,4-methylenedioxyphenyl)-3-(4-methoxy-2-hydroxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid
—— Butanoic acid (2E)-2-[(2-hydroxyphenyl)methylene]hydrazide 263153-47-5 C11H14N2O2
Butanoic acid (2E)-2-[(2-hydroxyphenyl)methylene]hydrazide
—— 2-Fluor-4-sec-pentyl-phenol 3832-81-3 C11H15FO
2-Fluor-4-sec-pentyl-phenol
—— 2,2,2-Trifluoro-N,N-bis-[2-(3-hydroxy-4-methoxy-phenyl)-ethyl]-acetamide 75608-45-6 C20H22F3NO5
2,2,2-Trifluoro-N,N-bis-[2-(3-hydroxy-4-methoxy-phenyl)-ethyl]-acetamide
—— 97035-06-8 C13H10BrNO4
—— 5-(4-Hydroxy-phenyl)-1,2,3,4-thiatriazol 91589-07-0 C7H5N3OS
5-(4-Hydroxy-phenyl)-1,2,3,4-thiatriazol
—— 3-chloro-6-nitro-2-(1-pyrrolidinylcarbonyl)phenol 934275-51-1 C11H11ClN2O4
3-chloro-6-nitro-2-(1-pyrrolidinylcarbonyl)phenol
—— 2-Amino-4-methyl-6-(2-hydroxy-α-methylbenzylidenhydrazino)-pyrimidin 91960-34-8 C13H15N5O
2-Amino-4-methyl-6-(2-hydroxy-α-methylbenzylidenhydrazino)-pyrimidin
—— N'-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-3-nitrobenzohydrazide 303065-92-1 C15H12BrN3O5
N'-(3-Bromo-4-hydroxy-5-methoxybenzylidene)-3-nitrobenzohydrazide
—— 3-(diethylamino)-5-(2,4-dihydroxyphenyl)isoxazole 153528-51-9 C13H16N2O3
3-(diethylamino)-5-(2,4-dihydroxyphenyl)isoxazole
—— 2-(4,5-dihydro-1<i>H</i>-imidazol-2-ylamino)-benzene-1,3-diol 78249-70-4 C9H11N3O2
2-(4,5-dihydro-1<i>H</i>-imidazol-2-ylamino)-benzene-1,3-diol
—— 4-(2,4-diamino-6-butylsulfanyl-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenol 39667-24-8 C17H24N4O3S
4-(2,4-diamino-6-butylsulfanyl-pyrimidin-5-ylmethyl)-2,6-dimethoxy-phenol
—— 2-(5-Chlor-4-nitro-2-hydroxyphenylhydrazono)-propionsaeureaethylester 19169-36-9 C11H12ClN3O5
2-(5-Chlor-4-nitro-2-hydroxyphenylhydrazono)-propionsaeureaethylester