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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
—— N-[(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-2-carboxamide 341981-65-5 C13H10N4O4
N-[(5-hydroxy-2-nitrophenyl)methylideneamino]pyridine-2-carboxamide
—— 6,8,9-trichloro-7-hydroxy-2-(pyridin-2-yl)benzo[f][1,3,4]-oxadiazepin-5-(4H)-one 1217805-81-6 C13H6Cl3N3O3
6,8,9-trichloro-7-hydroxy-2-(pyridin-2-yl)benzo[f][1,3,4]-oxadiazepin-5-(4H)-one
—— 4-Methoxy-2-octyl-phenol 19368-92-4 C15H24O2
4-Methoxy-2-octyl-phenol
—— 2-butyl-phloroglucinol 96756-18-2 C10H14O3
2-butyl-phloroglucinol
—— 2-octylbenzene-1,3,5-triol 85292-81-5 C14H22O3
2-octylbenzene-1,3,5-triol
—— 2-pentyl-phloroglucinol 66711-54-4 C11H16O3
2-pentyl-phloroglucinol
—— 4-methoxy-3-(3-methoxypropoxy)phenol 960216-36-8 C11H16O4
4-methoxy-3-(3-methoxypropoxy)phenol
—— 5,11,17,23-Tetrabenzyl-25,26,27,28-tetrahydroxycalix<4>arene 139934-43-3 C56H48O4
5,11,17,23-Tetrabenzyl-25,26,27,28-tetrahydroxycalix<4>arene
—— 5,11,17,23-tetrakis(dihydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix<4>arene 124006-40-2 C32H36O16P4
5,11,17,23-tetrakis(dihydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix<4>arene
—— benzene-1,3,5-triol; deprotonated form 20208-84-8 C6H5O3
benzene-1,3,5-triol; deprotonated form
—— methyl 3-(4-hydroxyphenyl)hexanoate 1356601-60-9 C13H18O3
methyl 3-(4-hydroxyphenyl)hexanoate
—— 2-[[Tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde 388570-73-8 C25H28O4Si
2-[[Tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde
—— (R)-methyl 3-(4-hydroxyphenyl)hex-4-ynoate 929713-77-9 C13H14O3
(R)-methyl 3-(4-hydroxyphenyl)hex-4-ynoate
—— eucomic acid dimethyl ester 60449-49-2 C13H16O6
eucomic acid dimethyl ester
—— 3-n-Octyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion 93959-18-3 C18H23NO2S2
3-n-Octyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion
—— (Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-thioxothiazolidin-2-one 1401235-18-4 C12H11NO4S2
(Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-thioxothiazolidin-2-one
—— (+/-)-3-(1-hydroxy-2-dimethylamino-ethyl)-phenol 93202-79-0 C10H15NO2
(+/-)-3-(1-hydroxy-2-dimethylamino-ethyl)-phenol
—— trimethylamine picrate 7468-01-1 C3H9N*C6H3N3O7
trimethylamine picrate
—— (+/-)-4-Hydroxy-1-(1-methyl-heptadecyl)-benzol 88928-35-2 C24H42O
(+/-)-4-Hydroxy-1-(1-methyl-heptadecyl)-benzol
—— 1-(Cyclohex-2-en-1-on-4-yl)-2-(4-hydroxyphenyl)-ethane 129579-59-5 C14H16O2
1-(Cyclohex-2-en-1-on-4-yl)-2-(4-hydroxyphenyl)-ethane
—— (Z)-4-thioxo-5-(2,3,4-trihydroxybenzylidene)thiazolidin-2-one 1401235-09-3 C10H7NO4S2
(Z)-4-thioxo-5-(2,3,4-trihydroxybenzylidene)thiazolidin-2-one
—— 5-(4-hydroxy-3-methoxy-benzylidene)-4-thioxo-thiazolidin-2-one 16878-95-8 C11H9NO3S2
5-(4-hydroxy-3-methoxy-benzylidene)-4-thioxo-thiazolidin-2-one
—— 5-[(3,4-Dihydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one 1171047-12-3 C10H7NO3S2
5-[(3,4-Dihydroxyphenyl)methylidene]-4-sulfanylidene-1,3-thiazolidin-2-one
—— 4-[5-(2-hydroxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-2(5H)-one 1149372-34-8 C18H15N3O2S
4-[5-(2-hydroxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-1,3-thiazol-2(5H)-one
—— (Z)-5-(3-hydroxybenzylidene)-4-thioxothiazolidin-2-one 1401235-12-8 C10H7NO2S2
(Z)-5-(3-hydroxybenzylidene)-4-thioxothiazolidin-2-one
—— (Z)-5-(2,3-dihydroxybenzylidene)-4-thioxo-thiazolidine-2-one 1365266-80-3 C10H7NO3S2
(Z)-5-(2,3-dihydroxybenzylidene)-4-thioxo-thiazolidine-2-one
—— 2,5-Dinitro-vanillin 2698-73-9 C8H6N2O7
2,5-Dinitro-vanillin
—— 2-[2-hydroxy-3-(hydroxymethyl)-5-methylbenzylideneamino]-2-methylpropane-1,3-diol 1610459-14-7 C13H19NO4
2-[2-hydroxy-3-(hydroxymethyl)-5-methylbenzylideneamino]-2-methylpropane-1,3-diol
—— (Z)-5-(2,4-dihydroxybenzylidene)-4-thioxothiazolidin-2-one 1401235-05-9 C10H7NO3S2
(Z)-5-(2,4-dihydroxybenzylidene)-4-thioxothiazolidin-2-one
—— (Z)-5-(2-hydroxybenzylidene)-4-thioxothiazolidin-2-one 1401235-14-0 C10H7NO2S2
(Z)-5-(2-hydroxybenzylidene)-4-thioxothiazolidin-2-one
—— 3-chloro-4-methyl-2-nitro-phenol 112251-93-1 C7H6ClNO3
3-chloro-4-methyl-2-nitro-phenol
—— 4-methyl-2-((trimethylsilyl)ethynyl)phenol 183589-03-9 C12H16OSi
4-methyl-2-((trimethylsilyl)ethynyl)phenol
—— 2,6-dibromo-3,4,5-trimethylphenol 57825-70-4 C9H10Br2O
2,6-dibromo-3,4,5-trimethylphenol
—— yahazunol 69809-36-5 C21H32O3
yahazunol
—— 1-chloro-2-(4-hydroxyphenyl)propan-2-ol 98815-45-3 C9H11ClO2
1-chloro-2-(4-hydroxyphenyl)propan-2-ol
—— 2-(3-hydroxy-3-methyl)butyl-4-fluorophenol 353235-70-8 C11H15FO2
2-(3-hydroxy-3-methyl)butyl-4-fluorophenol
—— (Z)-6-(4-hydroxy-3-methoxyphenyl)-3-(selenophen-2-ylmethylene)indolin-2-one 1162189-83-4 C20H15NO3Se
(Z)-6-(4-hydroxy-3-methoxyphenyl)-3-(selenophen-2-ylmethylene)indolin-2-one
—— 2,4‐dibromo‐6‐[(4‐fluorobenzylimino)methyl]phenol 477848-41-2 C14H10Br2FNO
2,4‐dibromo‐6‐[(4‐fluorobenzylimino)methyl]phenol
—— (E)-3-(3-hydroxy-4-methoxybenzylidene)-6-methoxyindolin-2-one 1148119-15-6 C17H15NO4
(E)-3-(3-hydroxy-4-methoxybenzylidene)-6-methoxyindolin-2-one
—— (S)-DHTP —— C24H16O2
(S)-DHTP
—— 9,9-bis(4-hydroxyphenyl)-9-silafluorene 956904-39-5 C24H18O2Si
9,9-bis(4-hydroxyphenyl)-9-silafluorene
—— p-(2,2-dichloro-1-methylcyclopropyl)phenol 52178-68-4 C10H10Cl2O
p-(2,2-dichloro-1-methylcyclopropyl)phenol
—— (4aS,8aS)-N-(3-hydroxy-5-methoxyphenyl)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxamide 1619983-01-5 C22H31NO3
(4aS,8aS)-N-(3-hydroxy-5-methoxyphenyl)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxamide
—— (1S,2S,4aS,8aR)-1-[(3,5-dihydroxyphenyl)methyl]-5,5,8a-trimethyldecahydronaphthalene-2-carboxylic acid 1619983-67-3 C21H30O4
(1S,2S,4aS,8aR)-1-[(3,5-dihydroxyphenyl)methyl]-5,5,8a-trimethyldecahydronaphthalene-2-carboxylic acid
—— (1'R)-1'-(3-hydroxy-4-methoxyphenyl)ethane-1',2'-diol 213466-88-7 C9H12O4
(1'R)-1'-(3-hydroxy-4-methoxyphenyl)ethane-1',2'-diol
—— 2-hydroxy-<i>N</i>-methyl-thiobenzamide 7133-91-7 C8H9NOS
2-hydroxy-<i>N</i>-methyl-thiobenzamide
—— 5-{2-[(1S,2S,4aS,8aR)-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]ethyl}benzene-1,3-diol 1619983-18-4 C22H34O2
5-{2-[(1S,2S,4aS,8aR)-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl]ethyl}benzene-1,3-diol
—— 5-(4-fluorobenzyloxy)benzene-1,3-diol 1304772-13-1 C13H11FO3
5-(4-fluorobenzyloxy)benzene-1,3-diol
—— 2'-amino-6'-hydroxy-3',5'-dinitroacetanilide 88140-48-1 C8H8N4O6
2'-amino-6'-hydroxy-3',5'-dinitroacetanilide
—— (4S)-4-(3-chloro-4-hydroxy-phenyl)-5-(4-cyclohexylthiazol-2-yl)-6-ethyl-3,4-dihydro-1H-pyrimidin-2-one 1224735-92-5 C21H24ClN3O2S
(4S)-4-(3-chloro-4-hydroxy-phenyl)-5-(4-cyclohexylthiazol-2-yl)-6-ethyl-3,4-dihydro-1H-pyrimidin-2-one