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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
—— tetraformylresorcin[4]arene —— C48H56O12
tetraformylresorcin[4]arene
—— 4-(2,4-Dihydroxyphenyl)-3-cyclohexen-1-one —— C12H12O3
4-(2,4-Dihydroxyphenyl)-3-cyclohexen-1-one
—— (2R,3S,4S)-4-{[2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3-formyl-3,4-dihydro-2H-pyran-5-acetic acid methyl ester —— C19H22O8
(2R,3S,4S)-4-{[2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3-formyl-3,4-dihydro-2H-pyran-5-acetic acid methyl ester
—— 3,5-bis-(3,4-dihydroxybenzylidene)-1-methylpiperidin-4-one —— C20H19NO5
3,5-bis-(3,4-dihydroxybenzylidene)-1-methylpiperidin-4-one
—— (E)-4-(((2-hydroxyphenyl)imino)methyl)benzene-1,2-diol —— C13H11NO3
(E)-4-(((2-hydroxyphenyl)imino)methyl)benzene-1,2-diol
—— 5-(3,4-dihydroxybenzylidene)-3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one —— C18H15NO4S2
5-(3,4-dihydroxybenzylidene)-3-[2-(4-hydroxyphenyl)ethyl]-2-thioxothiazolidine-4-one
—— (E)-3-(3,4-dihydroxybenzylidene)pyrrolidine-2,5-dione —— C11H9NO4
(E)-3-(3,4-dihydroxybenzylidene)pyrrolidine-2,5-dione
—— N-methoxy-3,4-dihydroxybenzaldimine —— C8H9NO3
N-methoxy-3,4-dihydroxybenzaldimine
—— 3,5-bis(3,4-dihydroxybenz-(E)-ylidene)-4-piperidone hydrochloride —— C19H17NO5*ClH
3,5-bis(3,4-dihydroxybenz-(E)-ylidene)-4-piperidone hydrochloride
—— 5-(3,4-dihydroxybenzylidene)-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one —— C15H11NO4S2
5-(3,4-dihydroxybenzylidene)-3-(furan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
—— 1,1',2,2'-tetra-hydroxyl{4'',4'''-phenylenebis[aminomethyl]}bisphenol —— C20H16N2O4
1,1',2,2'-tetra-hydroxyl{4'',4'''-phenylenebis[aminomethyl]}bisphenol
—— (E)-4-(2-(dodecylsulfonyl)vinyl)benzene-1,2-diol —— C20H32O4S
(E)-4-(2-(dodecylsulfonyl)vinyl)benzene-1,2-diol
—— (Z)-3-(5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid —— C13H11NO5S2
(Z)-3-(5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid
—— N,N'-bis-(3-hydroxybenzylidene)benzene-1,4-diamine —— C20H16N2O2
N,N'-bis-(3-hydroxybenzylidene)benzene-1,4-diamine
—— (Z)-ethyl 5-(4-chlorophenyl)-2-(3,4-dihydroxybenzylidene)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate —— C23H19ClN2O5S
(Z)-ethyl 5-(4-chlorophenyl)-2-(3,4-dihydroxybenzylidene)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 3,4-dihydroxymandelamidoxime monohydrate —— C8H10N2O4*H2O
3,4-dihydroxymandelamidoxime monohydrate
—— (Z)-3-(3-bromobenzyl)-5-(3,4-dihydroxybenzylidene)thiazolidine-2,4-dione —— C17H12BrNO4S
(Z)-3-(3-bromobenzyl)-5-(3,4-dihydroxybenzylidene)thiazolidine-2,4-dione
—— 2-amino-4-(3,4-dihydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile —— C16H14N2O4
2-amino-4-(3,4-dihydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
—— (E)-4-(2-(octylsulfonyl)vinyl)benzene-1,2-diol —— C16H24O4S
(E)-4-(2-(octylsulfonyl)vinyl)benzene-1,2-diol
—— (E)-4-(2-((11-hydroxyundecyl)sulfonyl)vinyl)benzene-1,2-diol —— C19H30O5S
(E)-4-(2-((11-hydroxyundecyl)sulfonyl)vinyl)benzene-1,2-diol
—— (3E,5E)-1-cyclopropyl-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one —— C22H21NO5
(3E,5E)-1-cyclopropyl-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
—— (2Z,5E)-2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone —— C19H16O5
(2Z,5E)-2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone
—— (3Z,5Z)-3,5-bis(3,4-dihydroxybenzylidene)dihydro-2H-thiopyran-4(3H)-one —— C19H16O5S
(3Z,5Z)-3,5-bis(3,4-dihydroxybenzylidene)dihydro-2H-thiopyran-4(3H)-one
—— (3E,5E)-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one —— C19H17NO5
(3E,5E)-3,5-bis(3,4-dihydroxybenzylidene)piperidin-4-one
—— 6-amino-4-(3,4-dihydroxyphenyl)-3-propyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C16H16N4O3
6-amino-4-(3,4-dihydroxyphenyl)-3-propyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— 2-(diethoxyphosphoryl)-N-(3,4-dihydroxybenzylidene)propan-2-amine oxide —— C14H22NO6P
2-(diethoxyphosphoryl)-N-(3,4-dihydroxybenzylidene)propan-2-amine oxide
—— (3E,5E)-3,5-bis(3,4-dihydroxybenzylidene)dihydro-2H-pyran-4(3H)-one —— C19H16O6
(3E,5E)-3,5-bis(3,4-dihydroxybenzylidene)dihydro-2H-pyran-4(3H)-one
—— (E)-4-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)benzene-1,2-diol 1528690-50-7 C13H10N6O2S
(E)-4-((3-mercapto-5-(pyrazin-2-yl)-4H-1,2,4-triazol-4-ylimino)methyl)benzene-1,2-diol
—— (3E,5E)-3,5-bis(3,4-dihydroxybenzylidene)-1-methylpiperidin-4-one —— C20H19NO5
(3E,5E)-3,5-bis(3,4-dihydroxybenzylidene)-1-methylpiperidin-4-one
—— (E)-N'-(3,4-dihydroxybenzylidene)-2-((5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)thio)acetohydrazide 1480227-25-5 C16H13N5O4S
(E)-N'-(3,4-dihydroxybenzylidene)-2-((5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)thio)acetohydrazide
—— (2E,5E)-2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone —— C19H16O5
(2E,5E)-2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone
—— 3,4-dihydroxybenzyl-propargylamine —— C10H11NO2
3,4-dihydroxybenzyl-propargylamine
—— 6-amino-4-(3,4-dihydroxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile —— C14H12N4O3
6-amino-4-(3,4-dihydroxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
—— (E)-2-hydroxy-2-(3,4-dihydroxyphenyl)ethanaloxime —— C8H9NO4
(E)-2-hydroxy-2-(3,4-dihydroxyphenyl)ethanaloxime
—— 2-(hydroxy(pyridin-2-yl)methyl)phenol —— C12H11NO2
2-(hydroxy(pyridin-2-yl)methyl)phenol
—— α-Hydroxy-3-(azidomethyl)-4-hydroxybenzeneacetic acid —— C9H9N3O4
α-Hydroxy-3-(azidomethyl)-4-hydroxybenzeneacetic acid
—— 1-(3-(4-hydroxy-3-methoxyphenyl)propyl)-1-phenethyl-3-phenethylthiourea —— C27H32N2O2S
1-(3-(4-hydroxy-3-methoxyphenyl)propyl)-1-phenethyl-3-phenethylthiourea
—— 1-benzyl-1-(3-(4-hydroxy-3-methoxyphenyl)propyl)-3-phenethylthiourea —— C26H30N2O2S
1-benzyl-1-(3-(4-hydroxy-3-methoxyphenyl)propyl)-3-phenethylthiourea
—— 3-hydroxy-5-[hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-4-(4-hydroxy-3-methoxyphenyl)cyclopent-2-en-1-one —— C20H20O7
3-hydroxy-5-[hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-4-(4-hydroxy-3-methoxyphenyl)cyclopent-2-en-1-one
—— 15,16-bis(2-hydroxyphenyl)-1,4,8,11-tetraazatricyclo[9.3.1.1<sup>4,8</sup>]hexadecane —— C24H32N4O2
15,16-bis(2-hydroxyphenyl)-1,4,8,11-tetraazatricyclo[9.3.1.1<sup>4,8</sup>]hexadecane
—— N,N-dimethyl(2-hydroxyethyl)ammonium 2,4,6-trinitrophenolate —— C4H11NO*C6H3N3O7
N,N-dimethyl(2-hydroxyethyl)ammonium 2,4,6-trinitrophenolate
—— picrate of 2,2-diallyl-1-azacyclotridecane —— C6H3N3O7*C18H33N
picrate of 2,2-diallyl-1-azacyclotridecane
—— (4aR,8aR)-decahydroisoquinoline picrate —— C6H3N3O7*C9H17N
(4aR,8aR)-decahydroisoquinoline picrate
—— (4S)-4,5-dihydro-2-(4'-hydroxyphenyl)-4-isopropyloxyoxazole —— C12H15NO2
(4S)-4,5-dihydro-2-(4'-hydroxyphenyl)-4-isopropyloxyoxazole
—— (S)-2-fluoro-4-(1-hydroxyethyl)phenol —— C8H9FO2
(S)-2-fluoro-4-(1-hydroxyethyl)phenol
—— (S)-3-fluoro-4-(1-hydroxyethyl)phenol —— C8H9FO2
(S)-3-fluoro-4-(1-hydroxyethyl)phenol
—— 2-fluoro-4-(1-hydroxyethyl)phenol —— C8H9FO2
2-fluoro-4-(1-hydroxyethyl)phenol
—— 3-fluoro-4-(1-hydroxyethyl)phenol —— C8H9FO2
3-fluoro-4-(1-hydroxyethyl)phenol
—— (S)-3-chloro-4-(1-hydroxyethyl)phenol —— C8H9ClO2
(S)-3-chloro-4-(1-hydroxyethyl)phenol
—— 1-{2’-[(5''-bromopentyl)oxy]ethyl}-4-methoxybenzene —— C14H21BrO2
1-{2’-[(5''-bromopentyl)oxy]ethyl}-4-methoxybenzene