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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-(N,N-dimethylaminomethyl)benzene-1,4-diol 1250873-80-3 C9H13NO2
2-(N,N-dimethylaminomethyl)benzene-1,4-diol
—— 2-hydroxy-5-(methoxymethoxy)benzaldehyde 131223-63-7 C9H10O4
2-hydroxy-5-(methoxymethoxy)benzaldehyde
—— 2-bromo-3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-4-methoxyphenol 347840-54-4 C24H27BrO3Si
2-bromo-3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-4-methoxyphenol
—— 2-[(Methylamino)methyl]benzene-1,4-diol 229486-97-9 C8H11NO2
2-[(Methylamino)methyl]benzene-1,4-diol
—— (Z)-5-(2,5-dihydroxybenzylidene)-4-thioxothiazolidin-2-one 1401235-07-1 C10H7NO3S2
(Z)-5-(2,5-dihydroxybenzylidene)-4-thioxothiazolidin-2-one
—— 3-Bromo-5-hydroxy-2-(methoxymethoxy)benzaldehyde 881035-24-1 C9H9BrO4
3-Bromo-5-hydroxy-2-(methoxymethoxy)benzaldehyde
—— 4-isopropoxy-3-vinylphenol 321922-24-1 C11H14O2
4-isopropoxy-3-vinylphenol
—— 2-Bromo-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methoxy-6-(3-methylbut-2-enyl)phenol 347840-55-5 C29H35BrO3Si
2-Bromo-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methoxy-6-(3-methylbut-2-enyl)phenol
—— 2-(2',5'-dihydroxyphenyl)-1,3-dithiane 496043-34-6 C10H12O2S2
2-(2',5'-dihydroxyphenyl)-1,3-dithiane
—— (S)-methyl 3-(4-hydroxyphenyl)hex-4-ynoate 865233-36-9 C13H14O3
(S)-methyl 3-(4-hydroxyphenyl)hex-4-ynoate
—— 2-chloro-3,6-dihydroxy-benzaldehyde 32744-84-6 C7H5ClO3
2-chloro-3,6-dihydroxy-benzaldehyde
—— 2,5-dihydroxybenzaldehyde oxime 37110-11-5 C7H7NO3
2,5-dihydroxybenzaldehyde oxime
—— 2-(2,5-dihydroxyphenyl)vinylisocyanide 113093-47-3 C9H7NO2
2-(2,5-dihydroxyphenyl)vinylisocyanide
—— 4,5-dibromo-N-(2-(2,5-dihydroxyphenyl)-4-oxothiazolidin-3-yl)-1-methyl-1H-pyrrole-2-carboxamide 1415036-49-5 C15H13Br2N3O4S
4,5-dibromo-N-(2-(2,5-dihydroxyphenyl)-4-oxothiazolidin-3-yl)-1-methyl-1H-pyrrole-2-carboxamide
—— 5-(3,3-dimethylbutoxy)-2-hydroxybenzaldehyde 1300730-96-4 C13H18O3
5-(3,3-dimethylbutoxy)-2-hydroxybenzaldehyde
—— 3-bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)phenol 1622235-99-7 C13H21BrO2Si
3-bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)phenol
—— 5-methoxy-2-(1-propenyl)phenol 53889-55-7 C10H12O2
5-methoxy-2-(1-propenyl)phenol
—— 4-chloro-2-(3-chloro-2-propenyl)phenol 102117-77-1 C9H8Cl2O
4-chloro-2-(3-chloro-2-propenyl)phenol
—— 4-Hydroxybenzaldehyde N,N-dimethylhydrazone 22699-30-5 C9H12N2O
4-Hydroxybenzaldehyde N,N-dimethylhydrazone
—— 2-bromo-4-(2-bromo-1,1,2-trifluoroethoxy)-phenol 88553-93-9 C8H5Br2F3O2
2-bromo-4-(2-bromo-1,1,2-trifluoroethoxy)-phenol
—— N-cis-caffeoyl putrescine 29554-26-5 C13H18N2O3
N-cis-caffeoyl putrescine
—— ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate 102093-63-0 C11H15NO4
ethyl N-[2-(4-hydroxyphenoxy)ethyl]carbamate
—— 1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-(2,4-dichlorophenyl)-4,5-dihydropyrazol-1-yl)ethanone 1472645-96-7 C18H17Cl2N3O3
1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-(2,4-dichlorophenyl)-4,5-dihydropyrazol-1-yl)ethanone
—— 2-(β-t-Butylallyl)-phenol 92035-88-6 C13H18O
2-(β-t-Butylallyl)-phenol
—— N'-(5-bromo-2-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester 851205-58-8 C12H17BrN2O3
N'-(5-bromo-2-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester
—— (2Z)-2-[3-hydroxy-5-oxo-4-(3,4,5-trihydroxyphenyl)furan-2-ylidene]-2-(4-hydroxyphenyl)acetic acid 25328-77-2 C18H12O9
(2Z)-2-[3-hydroxy-5-oxo-4-(3,4,5-trihydroxyphenyl)furan-2-ylidene]-2-(4-hydroxyphenyl)acetic acid
—— 2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol 1000002-35-6 C10H10N2O2
2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol
—— 1,2-bis(2-hydroxyphenyl)diselenide 73011-32-2 C12H10O2Se2
1,2-bis(2-hydroxyphenyl)diselenide
—— 1,2,3-trihydroxy-4,6-dichlorobenzene 87441-03-0 C6H4Cl2O3
1,2,3-trihydroxy-4,6-dichlorobenzene
—— 4-Chloro-1,2,3-trihydroxybenzene 3598-34-3 C6H5ClO3
4-Chloro-1,2,3-trihydroxybenzene
—— 2,4,6-trimethylpyridinium picrate 6148-01-2 C6H3N3O7*C8H11N
2,4,6-trimethylpyridinium picrate
—— 2,6-diamino-4-(4-hydroxyphenyl)-4H-thiopyran-3,5-dicarbonitrile 221178-81-0 C13H10N4OS
2,6-diamino-4-(4-hydroxyphenyl)-4H-thiopyran-3,5-dicarbonitrile
—— 4-(((4-ethylphenyl)imino)methyl)phenol 67302-65-2 C15H15NO
4-(((4-ethylphenyl)imino)methyl)phenol
—— 4,5-dihydro-4-(4-hydroxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one 1190002-42-6 C13H13N3O2
4,5-dihydro-4-(4-hydroxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one
—— (4-hydroxyphenyl)methylene-2-thioxo-4-thiazolidinone 6339-79-3 C10H7NO2S2
(4-hydroxyphenyl)methylene-2-thioxo-4-thiazolidinone
—— 4-((5-hydroxy-3-methyl-1H-pyrazol-4-yl)(2-hydroxyphenyl)methyl)-3-methyl-1H-pyrazol-5-ol 392670-70-1 C15H16N4O3
4-((5-hydroxy-3-methyl-1H-pyrazol-4-yl)(2-hydroxyphenyl)methyl)-3-methyl-1H-pyrazol-5-ol
—— ethyl (+/-)-4-(2'-hydroxy-5'-nitrophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate 105410-38-6 C14H15N3O6
ethyl (+/-)-4-(2'-hydroxy-5'-nitrophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate
—— 4-((5-hydroxy-3-methyl-1H-pyrazol-4-yl)(3-hydroxyphenyl)methyl)-3-methyl-1H-pyrazol-5-ol 432020-86-5 C15H16N4O3
4-((5-hydroxy-3-methyl-1H-pyrazol-4-yl)(3-hydroxyphenyl)methyl)-3-methyl-1H-pyrazol-5-ol
—— 4-hydroxybenzaldehyde didodecylthioacetal 849096-89-5 C31H56OS2
4-hydroxybenzaldehyde didodecylthioacetal
—— 4-(1,3-dithian-2-yl)phenol 57529-05-2 C10H12OS2
4-(1,3-dithian-2-yl)phenol
—— N-(4-hydroxybenzylidene)-1-diethoxyphosphoryl-1-methylethylamine N-oxide 913260-47-6 C14H22NO5P
N-(4-hydroxybenzylidene)-1-diethoxyphosphoryl-1-methylethylamine N-oxide
—— 5-(12-Heneicosenyl)-1,3-benzenediol 189562-00-3 C27H46O2
5-(12-Heneicosenyl)-1,3-benzenediol
—— (2E,7Z)-1-(4-hydroxy-3-methoxyphenyl)-9-(4-hydroxyphenyl)nona-2,7-diene-4,6-dione 91884-87-6 C22H22O5
(2E,7Z)-1-(4-hydroxy-3-methoxyphenyl)-9-(4-hydroxyphenyl)nona-2,7-diene-4,6-dione
—— (Z,Z)-2-Methyl-5-(8,11,14-pentadecatrienyl)-1,3-benzenediol 50423-15-9 C22H32O2
(Z,Z)-2-Methyl-5-(8,11,14-pentadecatrienyl)-1,3-benzenediol
—— 5-(12-Heptadecenyl)-1,3-benzenediol 103462-06-2 C23H38O2
5-(12-Heptadecenyl)-1,3-benzenediol
—— 2-Methyl-5-(8,11-pentadecadienyl)-1,3-benzenediol 50423-14-8 C22H34O2
2-Methyl-5-(8,11-pentadecadienyl)-1,3-benzenediol
—— Methylmercapto-N-<4-hydroxyphenyl>thioureaniumiodide 36757-82-1 C8H10N2OS*HI
Methylmercapto-N-<4-hydroxyphenyl>thioureaniumiodide
—— (2Z,7E)-1,9-bis(4-hydroxy-3-methoxyphenyl)nona-2,7-diene-4,6-dione 91884-86-5 C23H24O6
(2Z,7E)-1,9-bis(4-hydroxy-3-methoxyphenyl)nona-2,7-diene-4,6-dione
—— 2-n-pentyl-1,4-dihydroxybenzene 4693-32-7 C11H16O2
2-n-pentyl-1,4-dihydroxybenzene
—— 2-hydroxy-3-methoxycinnamaldehyde 333754-89-5 C10H10O3
2-hydroxy-3-methoxycinnamaldehyde