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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
—— 3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid (5-methoxy-hexyl)-amide; compound with picric acid 117835-33-3 C6H3N3O7*C13H24N4O2
3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid (5-methoxy-hexyl)-amide; compound with picric acid
—— 6,6,6',6'-tetramethyl-3,6,3',6'-tetrahydro-1<i>H</i>,1'<i>H</i>-4,4'-[2-(2-hydroxy-phenyl)-propane-1,3-diyl]-bis-pyrimidin-2-one 27424-28-8 C21H28N4O3
6,6,6',6'-tetramethyl-3,6,3',6'-tetrahydro-1<i>H</i>,1'<i>H</i>-4,4'-[2-(2-hydroxy-phenyl)-propane-1,3-diyl]-bis-pyrimidin-2-one
—— (E)-methyl 3-(4-hydroxy-3,5-diiodophenyl)-2-(hydroxyimino)propanoate 1314789-40-6 C10H9I2NO4
(E)-methyl 3-(4-hydroxy-3,5-diiodophenyl)-2-(hydroxyimino)propanoate
—— 4-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-phenol 73428-20-3 C15H15NO2
4-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-phenol
—— 2-{5-[(Z)-2-(4-Methoxy-phenyl)-vinyl]-isoxazol-3-yl}-4-methyl-phenol 104387-47-5 C19H17NO3
2-{5-[(Z)-2-(4-Methoxy-phenyl)-vinyl]-isoxazol-3-yl}-4-methyl-phenol
—— N-(3-vinyloxycarbonylpropanoyl)metoprolol 1350626-99-1 C21H31NO6
N-(3-vinyloxycarbonylpropanoyl)metoprolol
—— 5-(o-Hydroxy-m-methoxybenzyliden)-3-methylisorhodanin 32085-69-1 C12H11NO3S2
5-(o-Hydroxy-m-methoxybenzyliden)-3-methylisorhodanin
—— (propylideneamino)phenol 38421-50-0 C9H11NO
(propylideneamino)phenol
—— 2-(3-fluoro-4-hydroxyphenyl)ethyl isothiocyanate 209911-51-3 C9H8FNOS
2-(3-fluoro-4-hydroxyphenyl)ethyl isothiocyanate
—— 1417303-98-0 C22H28O8
—— 3-Methyl-5-<4-methyl-anilino>pyrazol 23280-84-4 C10H6Cl4N2O2
3-Methyl-5-<4-methyl-anilino>pyrazol
—— N-(3-hydroxybenzyl)-N-(4-hydroxyphenethyl)acetamide 63144-68-3 C17H19NO3
N-(3-hydroxybenzyl)-N-(4-hydroxyphenethyl)acetamide
—— 3-(2-(2-hydroxy-3-methoxybenzylidene)hydrazineyl)isonicotinaldehyde 194782-54-2 C14H13N3O3
3-(2-(2-hydroxy-3-methoxybenzylidene)hydrazineyl)isonicotinaldehyde
—— tert-butyl (N-(4-hydroxyphenethyl)sulfamoyl)carbamate 1375958-98-7 C13H20N2O5S
tert-butyl (N-(4-hydroxyphenethyl)sulfamoyl)carbamate
—— 3-(4-hydroxyphenyl)-6-phenyl-7H-thiazolo[3,2-b][1,2,4]triazin-7-one 1186078-85-2 C17H11N3O2S
3-(4-hydroxyphenyl)-6-phenyl-7H-thiazolo[3,2-b][1,2,4]triazin-7-one
—— 7-(p-methoxyphenylazo)-2-(p-methoxyphenylmethylene)-8-hydroxy-6-methyl-2,3,4,5-tetrahydropyrido-[3,2-f][1,4]thiazepine-3,5-dione 1393809-62-5 C24H20N4O5S
7-(p-methoxyphenylazo)-2-(p-methoxyphenylmethylene)-8-hydroxy-6-methyl-2,3,4,5-tetrahydropyrido-[3,2-f][1,4]thiazepine-3,5-dione
—— (2S,5R)-2-(3,5-dibenzyloxy-4-methoxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]-5-isopropylimidazolidin-4-one 722499-86-7 C35H38N2O5
(2S,5R)-2-(3,5-dibenzyloxy-4-methoxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]-5-isopropylimidazolidin-4-one
—— sodium 2-(3-(2,3,4-trihydroxyphenyl)propanamido)ethane-1-sulfonate 1228675-83-9 C11H14NO7S*Na
sodium 2-(3-(2,3,4-trihydroxyphenyl)propanamido)ethane-1-sulfonate
—— 2-(1,3-dimethylcyclohex-3-en-1-yl)phenol 1380332-23-9 C14H18O
2-(1,3-dimethylcyclohex-3-en-1-yl)phenol
—— 5-Hydroxy-2-methoxy-mandelsaeure 56979-71-6 C9H10O5
5-Hydroxy-2-methoxy-mandelsaeure
—— Acetic acid N'-[1-cyano-2-(4-hydroxy-3-methoxy-phenyl)-1-methyl-ethyl]-hydrazide 28875-95-8 C13H17N3O3
Acetic acid N'-[1-cyano-2-(4-hydroxy-3-methoxy-phenyl)-1-methyl-ethyl]-hydrazide
—— 4-(4-chloro-phenyl)-3-(4-hydroxy-3-methoxy-benzylideneamino)-3<i>H</i>-thiazole-2-thione 23150-24-5 C17H13ClN2O2S2
4-(4-chloro-phenyl)-3-(4-hydroxy-3-methoxy-benzylideneamino)-3<i>H</i>-thiazole-2-thione
—— 3.4.6-Tris-(morpholinomethyl)-brenzcatechin 6452-84-2 C21H33N3O5
3.4.6-Tris-(morpholinomethyl)-brenzcatechin
—— 1384118-65-3 C24H38EuN10O3
—— p-<β-(((trimethylsilylethoxy)carbonyl)amino)ethyl>phenol 149838-25-5 C14H23NO3Si
p-<β-(((trimethylsilylethoxy)carbonyl)amino)ethyl>phenol
—— (3-<sup>14</sup>C)p-Coumarsaeure 50816-83-6 C9H8O3
(3-<sup>14</sup>C)p-Coumarsaeure
—— N-(4-Hydroxy-3-methoxyphenethyl)-4-(4-benzyloxy-3-bromphenyl)-butyramid 22320-15-6 C26H28BrNO4
N-(4-Hydroxy-3-methoxyphenethyl)-4-(4-benzyloxy-3-bromphenyl)-butyramid
—— (2Z)-2-(2-hydroxy-5-Bromobenzylidine)hydrazine N-methylcarbothioamide 41377-09-7 C9H10BrN3OS
(2Z)-2-(2-hydroxy-5-Bromobenzylidine)hydrazine N-methylcarbothioamide
—— N,N'-(3-chloro-4-hydroxy-benzylidene)-bis-propionamide 107149-89-3 C13H17ClN2O3
N,N'-(3-chloro-4-hydroxy-benzylidene)-bis-propionamide
—— (4-Hydroxyphenyl)acetaldehyd-dimethylhydrazon 74321-28-1 C10H14N2O
(4-Hydroxyphenyl)acetaldehyd-dimethylhydrazon
—— 4-Bromo-2-[[5-[(5-bromo-2-hydroxyphenyl)methylideneamino]-3-hydroxypentyl]iminomethyl]phenol 263872-38-4 C19H20Br2N2O3
4-Bromo-2-[[5-[(5-bromo-2-hydroxyphenyl)methylideneamino]-3-hydroxypentyl]iminomethyl]phenol
—— 2-hydroxyphenyldiazonium chloride 19183-06-3 C6H5N2O*Cl
2-hydroxyphenyldiazonium chloride
—— Tert-butyl (6-((6-((4-hydroxyphenethyl)amino)-6-oxohexyl)amino)-6-oxohexyl)carbamate 1048007-85-7 C25H41N3O5
Tert-butyl (6-((6-((4-hydroxyphenethyl)amino)-6-oxohexyl)amino)-6-oxohexyl)carbamate
—— 3-hydroxy-benzaldehyde dimethyldithioacetal 24396-28-9 C9H12OS2
3-hydroxy-benzaldehyde dimethyldithioacetal
—— 2-Iodo-4-phenylmethoxyphenol 1262524-15-1 C13H11IO2
2-Iodo-4-phenylmethoxyphenol
—— 3-Me-1,5-bis(salicylidenamino)pentan-3-ol 917596-72-6 C21H26N2O3
3-Me-1,5-bis(salicylidenamino)pentan-3-ol
—— 1,5-bis(salicylideneamino)-3-pentanol 81555-05-7 C19H22N2O3
1,5-bis(salicylideneamino)-3-pentanol
—— 2,5-bis[(3-allyl-2-hydroxy)phenyl]-1,3,4-thiadiazole 1206617-33-5 C20H18N2O2S
2,5-bis[(3-allyl-2-hydroxy)phenyl]-1,3,4-thiadiazole
—— ethyl 5-(4-hydroxyphenoxy)pentanoate 892861-29-9 C13H18O4
ethyl 5-(4-hydroxyphenoxy)pentanoate
—— 2-(1-hydroxy-5-methylhex-5-en-1-yl)-4-methoxyphenol 1380332-44-4 C14H20O3
2-(1-hydroxy-5-methylhex-5-en-1-yl)-4-methoxyphenol
—— (3-13C)phenol 70211-38-0 C6H6O
(3-13C)phenol
—— 1-<2-(4-Hydroxyphenyl)ethyl>-2,6-dimethyl-4,1-thiazane 4,4-dioxide 114600-98-5 C14H21NO3S
1-<2-(4-Hydroxyphenyl)ethyl>-2,6-dimethyl-4,1-thiazane 4,4-dioxide
—— 4,6-dibromoolivetol 78463-34-0 C11H14Br2O2
4,6-dibromoolivetol
—— 1-butyl-1<i>H</i>-imidazole; picrate 107054-84-2 C6H3N3O7*C7H12N2
1-butyl-1<i>H</i>-imidazole; picrate
—— 2-(1-hydroxy-5-methylhex-5-en-1-yl)-3,5-dimethoxyphenol 1380332-48-8 C15H22O4
2-(1-hydroxy-5-methylhex-5-en-1-yl)-3,5-dimethoxyphenol
—— methyl 2-hydroxybenzimidate hydrochloride 61636-46-2 C8H9NO2*ClH
methyl 2-hydroxybenzimidate hydrochloride
—— 5-but-2-enyl-2-methyl-pyridine; picrate 861019-11-6 C6H3N3O7*C10H13N
5-but-2-enyl-2-methyl-pyridine; picrate
—— 2-(((2-(1H-imidazol-4-yl)ethyl)imino)methyl)phenol 83001-62-1 C12H13N3O
2-(((2-(1H-imidazol-4-yl)ethyl)imino)methyl)phenol
—— 2-(2-hydroxy-6-methylhept-6-en-2-yl)-4-methoxyphenol 1380332-32-0 C15H22O3
2-(2-hydroxy-6-methylhept-6-en-2-yl)-4-methoxyphenol
—— 1,11-bis(4-hydroxyphenoxy)-3,6,9-trioxaundecane 14556-10-6 C20H26O7
1,11-bis(4-hydroxyphenoxy)-3,6,9-trioxaundecane