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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
—— Picric acid; compound with [2-(2-amino-ethyl)-1H-imidazol-4-yl]-methanol 82765-59-1 2C6H3N3O7*C6H11N3O
Picric acid; compound with [2-(2-amino-ethyl)-1H-imidazol-4-yl]-methanol
—— diethyl 2-hydroxy-3-methylphenyl phosphonate 80615-38-9 C11H17O4P
diethyl 2-hydroxy-3-methylphenyl phosphonate
—— (E)-4-[(2-hydroxy-3-methoxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 1418275-12-3 C14H17N5O3S
(E)-4-[(2-hydroxy-3-methoxybenzylidene)amino]-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one
—— 1,2-Dihydroxy-3-<mercapto-methyl>-benzol 5590-08-9 C7H8O2S
1,2-Dihydroxy-3-<mercapto-methyl>-benzol
—— 1-(4-oxopent-2-ylideneamino)-2-[(2-hydroxyphenyl)ethylideneamino]benzene 1352278-68-2 C19H20N2O2
1-(4-oxopent-2-ylideneamino)-2-[(2-hydroxyphenyl)ethylideneamino]benzene
—— 1611492-14-8 C38H32O4P2Pd
—— 5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38-[2-[[(5-nitro-2-hydroxy)benzyl]amino]ethoxy]-40,42-bis[(1-methyl-2-imidazolyl)methoxy]calix[6]arene 649555-68-0 C88H112N6O9
5,11,17,23,29,35-hexa-tert-butyl-37,39,41-trimethoxy-38-[2-[[(5-nitro-2-hydroxy)benzyl]amino]ethoxy]-40,42-bis[(1-methyl-2-imidazolyl)methoxy]calix[6]arene
—— Pyrogallol-2-ethyl-ether 55020-70-7 C8H10O3
Pyrogallol-2-ethyl-ether
—— 4-(2-hydroxy-4-methoxy-phenyl)-3H-thiazol-2-one 90924-57-5 C10H9NO3S
4-(2-hydroxy-4-methoxy-phenyl)-3H-thiazol-2-one
—— N-Dichloracetyl-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin 19161-60-5 C9H7Cl3N2O2
N-Dichloracetyl-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin
—— 4-Hydroxy-2-methyl-dithiobenzoic acid methyl ester 116138-48-8 C9H10OS2
4-Hydroxy-2-methyl-dithiobenzoic acid methyl ester
—— 4-benzyloxy-6-bromo-3-hydroxybenzyl alcohol 130400-91-8 C14H13BrO3
4-benzyloxy-6-bromo-3-hydroxybenzyl alcohol
—— 2,5-bis-(2-chloro-ethylamino)-hydroquinone 99177-88-5 C10H14Cl2N2O2
2,5-bis-(2-chloro-ethylamino)-hydroquinone
—— Methyl 2-diazo-3-[4-methoxy-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]propanoate 334017-62-8 C17H23N3O5
Methyl 2-diazo-3-[4-methoxy-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]propanoate
—— 2-bromo-6-tert-butyldimethylsilyl-4-fluorophenol 1089665-87-1 C12H18BrFOSi
2-bromo-6-tert-butyldimethylsilyl-4-fluorophenol
—— 4-sec-Hexyl-2-brom-m-cresol 2950-79-0 C13H19BrO
4-sec-Hexyl-2-brom-m-cresol
—— 3-(5-(4-chlorophenyl)-4,5-dihydroisoxazol-3-yl)phenol 1421504-76-8 C15H12ClNO2
3-(5-(4-chlorophenyl)-4,5-dihydroisoxazol-3-yl)phenol
—— 3,4-dibromo-2-methyl-6-nitro-phenol 861576-26-3 C7H5Br2NO3
3,4-dibromo-2-methyl-6-nitro-phenol
—— 1611470-72-4 C15H21FN2O3
—— 3-fluoro-6-nitroso-phenol 2369-08-6 C6H4FNO2
3-fluoro-6-nitroso-phenol
—— 4-Ethyl-5-fluoro-benzene-1,2-diol 158641-48-6 C8H9FO2
4-Ethyl-5-fluoro-benzene-1,2-diol
—— 2-Methyl-3-ethyl-4-(m-hydroxyphenyl)-4-cyclohexencarbonsaeure 28229-81-4 C16H20O3
2-Methyl-3-ethyl-4-(m-hydroxyphenyl)-4-cyclohexencarbonsaeure
—— 3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]propanamide 634884-76-7 C16H20N4O3
3-(3,5-dimethyl-1H-pyrazol-4-yl)-N-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]propanamide
—— 2-{[(E)-1-Ethyl-propylimino]-methyl}-phenol 31411-74-2 C12H17NO
2-{[(E)-1-Ethyl-propylimino]-methyl}-phenol
—— 4-Chloro-2-[(methylnitrosoamino)methyl]phenol 89981-26-0 C8H9ClN2O2
4-Chloro-2-[(methylnitrosoamino)methyl]phenol
—— 4-Methoxy-N-salicyliden-2-aminopropan 42551-70-2 C11H15NO2
4-Methoxy-N-salicyliden-2-aminopropan
—— dimethyl ((butyl((dimethoxyphosphoryl)methyl)amino)(4-hydroxyphenyl)methyl)phosphonate 1185728-63-5 C16H29NO7P2
dimethyl ((butyl((dimethoxyphosphoryl)methyl)amino)(4-hydroxyphenyl)methyl)phosphonate
—— 5-(4-Hydroxy-3-methyl-phenyl)-2-methyl-pentane-2,3-diol 850201-26-2 C13H20O3
5-(4-Hydroxy-3-methyl-phenyl)-2-methyl-pentane-2,3-diol
—— N-[2-(3-chlorophenyl)ethyl]-2-(3,4,5-trihydroxyphenyl)acetamide 1447160-32-8 C16H16ClNO4
N-[2-(3-chlorophenyl)ethyl]-2-(3,4,5-trihydroxyphenyl)acetamide
—— N-(5-amino-4-((4-hydroxyphenyl)diazenyl)-1H-pyrazol-3-yl)acetamide 1374432-02-6 C11H12N6O2
N-(5-amino-4-((4-hydroxyphenyl)diazenyl)-1H-pyrazol-3-yl)acetamide
—— 2-(Cyclopentyliminomethyl)-5-methoxyphenol 1323952-05-1 C13H17NO2
2-(Cyclopentyliminomethyl)-5-methoxyphenol
—— N-[2-(4-hydroxyphenyl)ethyl]-2-(3,4,5-trihydroxyphenyl)acetamide 1447160-33-9 C16H17NO5
N-[2-(4-hydroxyphenyl)ethyl]-2-(3,4,5-trihydroxyphenyl)acetamide
—— 4,5-Dimethoxy-3,6-dihydroxyphthalaldehyd 52643-61-5 C10H10O6
4,5-Dimethoxy-3,6-dihydroxyphthalaldehyd
—— 2,4-Dihydroxy-5-isopentyl-benzaldehyd-4-propyl-thiosemicarbazon 18965-10-1 C16H25N3O2S
2,4-Dihydroxy-5-isopentyl-benzaldehyd-4-propyl-thiosemicarbazon
—— 4-(4-hydroxy-3,5-dinitro-phenyl)-butyric acid 35456-35-0 C10H10N2O7
4-(4-hydroxy-3,5-dinitro-phenyl)-butyric acid
—— 7,19-dimethylhexacyclo<11.11.5.1<sup>3,23</sup>.1<sup>5,9</sup>.1<sup>11,15</sup>.1<sup>17,21</sup>>triatriaconta-1,3(32),5,7,9(33),11,13,15(30),17,19,21(31),23-dodecaene-30,31,32,33-tetraol 115914-48-2 C35H36O4
7,19-dimethylhexacyclo<11.11.5.1<sup>3,23</sup>.1<sup>5,9</sup>.1<sup>11,15</sup>.1<sup>17,21</sup>>triatriaconta-1,3(32),5,7,9(33),11,13,15(30),17,19,21(31),23-dodecaene-30,31,32,33-tetraol
—— monoaureate of 2,6-bis((diethylamino)methyl)-4-NO2-phenol 141784-04-5 AuCl4*C16H28N3O3
monoaureate of 2,6-bis((diethylamino)methyl)-4-NO2-phenol
—— 3-((2-((6-((2-((3,4-dihydroxyphenethyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)hexyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)-N,N,N-trimethylpropan-1-ammonium iodide 1421366-04-2 C28H40N5O6*I
3-((2-((6-((2-((3,4-dihydroxyphenethyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)hexyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)-N,N,N-trimethylpropan-1-ammonium iodide
—— 4-(3-butoxypropyl)benzene-1,2-diol 1012310-05-2 C13H20O3
4-(3-butoxypropyl)benzene-1,2-diol
—— 1032176-42-3 C21H21IN2O5S
—— N,N'-bis(4,6-dimethoxysalicylidene)-1,12-dodecanediamine 1334545-44-6 C30H44N2O6
N,N'-bis(4,6-dimethoxysalicylidene)-1,12-dodecanediamine
—— N-Adamantan-1-yl-N'-(4-hydroxy-2-methyl-phenyl)-guanidine; compound with sulfuric acid 133985-83-8 2C18H25N3O*H2O4S
N-Adamantan-1-yl-N'-(4-hydroxy-2-methyl-phenyl)-guanidine; compound with sulfuric acid
—— 5-(2-hydroxy-5-bromobenzylidene)-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-one 1416588-21-0 C13H8BrN3O2S2
5-(2-hydroxy-5-bromobenzylidene)-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-one
—— 4-[Butylamino(dimethoxyphosphoryl)methyl]phenol 1185728-66-8 C13H22NO4P
4-[Butylamino(dimethoxyphosphoryl)methyl]phenol
—— 4-amino-N'-[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboximidamide 796877-38-8 C12H14N6O4
4-amino-N'-[(E)-(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-1,2,5-oxadiazole-3-carboximidamide
—— 4-[(4-Hydroxyphenyl)-(1-methylcyclohexyl)methyl]phenol 96706-66-0 C20H24O2
4-[(4-Hydroxyphenyl)-(1-methylcyclohexyl)methyl]phenol
—— [(5-Chloro-2-hydroxyphenyl)methylideneamino]carbamic acid 6641-56-1 C8H7ClN2O3
[(5-Chloro-2-hydroxyphenyl)methylideneamino]carbamic acid
—— 1,4,6-trimethyl-1,2,3,4-tetrahydro-quinoxaline-5,8-diol 1375148-99-4 C11H16N2O2
1,4,6-trimethyl-1,2,3,4-tetrahydro-quinoxaline-5,8-diol
—— 3,4-bis-(4-hydroxy-3-methoxy-phenyl)-hexane-3,4-diol 14227-21-5 C20H26O6
3,4-bis-(4-hydroxy-3-methoxy-phenyl)-hexane-3,4-diol
—— ethyl (2,5-dihydroxyphenyl)phenylphosphinate 123228-69-3 C14H15O4P
ethyl (2,5-dihydroxyphenyl)phenylphosphinate