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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
—— 5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylphenol 1369414-58-3 C14H24O2Si
5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylphenol
—— N-<β-(3.4-Dihydroxyphenyl)-ethyl>-cyclohexancarboxamid 42600-76-0 C15H21NO3
N-<β-(3.4-Dihydroxyphenyl)-ethyl>-cyclohexancarboxamid
—— 3-(2-Ethylphenyl)-2-(2-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one 354545-04-3 C26H24N2O2S
3-(2-Ethylphenyl)-2-(2-ethylphenyl)imino-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidin-4-one
—— (R<sub>S</sub>)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-2-(p-tolylsulfinyl)ethanol 249931-47-3 C18H22O5S
(R<sub>S</sub>)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-2-(p-tolylsulfinyl)ethanol
—— 5-<1-(hydroxy)-1-(4-hydroxyphenyl)methyl>-3-thiophenesulfonamide 155954-67-9 C11H11NO4S2
5-<1-(hydroxy)-1-(4-hydroxyphenyl)methyl>-3-thiophenesulfonamide
—— 3-nitrosalicylaldehyde oxime 17580-64-2 C7H6N2O4
3-nitrosalicylaldehyde oxime
—— 4-[(3,5-dibromo-4-hydroxyphenyl)methyl]-6-methyl-2-(methylamino)-3-(phenylmethoxymethyl)-7,8-dihydro-4H-imidazo[4,5-d]azepin-5-one 1509904-00-0 C24H26Br2N4O3
4-[(3,5-dibromo-4-hydroxyphenyl)methyl]-6-methyl-2-(methylamino)-3-(phenylmethoxymethyl)-7,8-dihydro-4H-imidazo[4,5-d]azepin-5-one
—— 4-methyl-2-(tetrahydrofuran-2-yl)phenol 80810-53-3 C11H14O2
4-methyl-2-(tetrahydrofuran-2-yl)phenol
—— 2,6-dimethyl-4-(octadecylthiomethyl)phenol 1258429-69-4 C27H48OS
2,6-dimethyl-4-(octadecylthiomethyl)phenol
—— 5,11-diallylcalix[4]arene 181635-69-8 C34H32O4
5,11-diallylcalix[4]arene
—— 3-methoxy-2-hydroxy-5-chlorotoluene 86232-26-0 C8H9ClO2
3-methoxy-2-hydroxy-5-chlorotoluene
—— 3-Hydroxy-2,6-dinitro-5-(2-nitro-phenylsulfanyl)-benzoic acid 81384-32-9 C13H7N3O9S
3-Hydroxy-2,6-dinitro-5-(2-nitro-phenylsulfanyl)-benzoic acid
—— 6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one 288839-59-8 C11H7NO4
6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one
—— 6-hydroxy-3-methoxy-5-propylanthranilamide 138224-09-6 C11H16N2O3
6-hydroxy-3-methoxy-5-propylanthranilamide
—— 7-allyl-6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one 288839-62-3 C14H11NO4
7-allyl-6,8-dihydroxy-9H-benzo [e]pyrrolo[2,1-b][1,3]oxazin-9-one
—— 1,4,5,8,9,12,13,16-octahydroxytetra-o-phenylene 511303-95-0 C24H16O8
1,4,5,8,9,12,13,16-octahydroxytetra-o-phenylene
—— 2,3-diethynyl 5,6-dimethylhydroquinone 198124-89-9 C12H10O2
2,3-diethynyl 5,6-dimethylhydroquinone
—— 2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol 198124-88-8 C18H26O2Si2
2,3-Dimethyl-5,6-bis(2-trimethylsilylethynyl)benzene-1,4-diol
—— 4-morpholin-4-ylmethyl-benzene-1,2,3-triol 41273-92-1 C11H15NO4
4-morpholin-4-ylmethyl-benzene-1,2,3-triol
—— 4-(7-carboxy-1,1-dimethyl-3-oxaheptyl )-5-(3-hydroxyphenyl)-3,3-dimethyl-2,3-dihydrofuran 594859-80-0 C21H30O5
4-(7-carboxy-1,1-dimethyl-3-oxaheptyl )-5-(3-hydroxyphenyl)-3,3-dimethyl-2,3-dihydrofuran
—— 2-<bis(trimethylsilyl)methyl>phenol 101145-02-2 C13H24OSi2
2-<bis(trimethylsilyl)methyl>phenol
—— (4'-hydroxy-3',5'-dinitrophenyl)(3-phenyloxiran-2-yl)methanone 1418203-05-0 C15H10N2O7
(4'-hydroxy-3',5'-dinitrophenyl)(3-phenyloxiran-2-yl)methanone
—— 2,3,4-trihydroxy-5-morpholin-4-ylmethyl-benzaldehyde 41273-96-5 C12H15NO5
2,3,4-trihydroxy-5-morpholin-4-ylmethyl-benzaldehyde
—— 2,4,5-trihydroxy-3-morpholin-4-ylmethyl-benzaldehyde 41273-90-9 C12H15NO5
2,4,5-trihydroxy-3-morpholin-4-ylmethyl-benzaldehyde
—— N’-(2-hydroxybenzylidene)-3,4,5-trihydroxybenzoylhydrazone 25054-55-1 C14H12N2O5
N’-(2-hydroxybenzylidene)-3,4,5-trihydroxybenzoylhydrazone
—— 1-amino-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol 95586-80-4 C12H19NO3
1-amino-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol
—— 4-[((E)-4-fluorophenylimino)methyl]benzene-1,3-diol 1334714-13-4 C13H10FNO2
4-[((E)-4-fluorophenylimino)methyl]benzene-1,3-diol
—— p-tert-butylcalix<4>arene triphosphate 175791-91-0 C56H83O13P3
p-tert-butylcalix<4>arene triphosphate
—— N,N-diethyl-3,4-dihydroxy-5-nitrobenzamide 134611-63-5 C11H14N2O5
N,N-diethyl-3,4-dihydroxy-5-nitrobenzamide
—— 2-<i>tert</i>-butyl-4-methoxy-6-morpholin-4-ylmethyl-phenol 21594-90-1 C16H25NO3
2-<i>tert</i>-butyl-4-methoxy-6-morpholin-4-ylmethyl-phenol
—— 1,3-Benzodioxol-5-ylmethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 5602-26-6 C21H19BrN2O7
1,3-Benzodioxol-5-ylmethyl 4-(3-bromo-4-hydroxy-5-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
—— 2,4-Dinitro-5-hydroxy-3-carboxy-6-methylphenyl 2-nitro-3-carboxy-6-methylphenyl sulfide 111837-72-0 C16H11N3O11S
2,4-Dinitro-5-hydroxy-3-carboxy-6-methylphenyl 2-nitro-3-carboxy-6-methylphenyl sulfide
—— 2,6-bis(trimethylsilyl)-4-methylphenol 18033-63-1 C13H24OSi2
2,6-bis(trimethylsilyl)-4-methylphenol
—— 5-(4-hydroxy-phenyl)-3-morpholinomethyl-3<i>H</i>-[1,3,4]oxadiazol-2-one 108487-85-0 C13H15N3O4
5-(4-hydroxy-phenyl)-3-morpholinomethyl-3<i>H</i>-[1,3,4]oxadiazol-2-one
—— 5-(4-hydroxy-phenyl)-3<i>H</i>-[1,3,4]oxadiazol-2-one 120035-90-7 C8H6N2O3
5-(4-hydroxy-phenyl)-3<i>H</i>-[1,3,4]oxadiazol-2-one
—— 1,4-bis(2-hydroxy-5-methoxybenzyl)piperazine 24773-81-7 C20H26N2O4
1,4-bis(2-hydroxy-5-methoxybenzyl)piperazine
—— Tetraethyl (2,3-dihydroxy-1,4-phenylene)bis(phosphonate) 91633-17-9 C14H24O8P2
Tetraethyl (2,3-dihydroxy-1,4-phenylene)bis(phosphonate)
—— 2-hydroxy-3-methoxy-5-morpholinomethyl-benzaldehyde ; hydrochloride 106275-18-7 C13H17NO4*ClH
2-hydroxy-3-methoxy-5-morpholinomethyl-benzaldehyde ; hydrochloride
—— (2,3-difluoro-6-hydroxyphenyl)boronic acid 1238196-62-7 C6H5BF2O3
(2,3-difluoro-6-hydroxyphenyl)boronic acid
—— 5-(2-hydroxybenzylidene)-2-imino-1,3-thiazolidin- 321579-48-0 C10H8N2O2S
5-(2-hydroxybenzylidene)-2-imino-1,3-thiazolidin-
—— 6-hexyl-4-(2-thiazolylazo)resorcinol 14383-66-5 C15H19N3O2S
6-hexyl-4-(2-thiazolylazo)resorcinol
—— 2-(3-Bromophenyl)-3-(5-chloro-2-hydroxyphenyl)-4-thiazolidinone 388604-55-5 C15H11BrClNO2S
2-(3-Bromophenyl)-3-(5-chloro-2-hydroxyphenyl)-4-thiazolidinone
—— 2-(p-hydroxyphenyl)-4,4,5,5-tetramethyl-1,3-dioxolan 78034-62-5 C13H18O3
2-(p-hydroxyphenyl)-4,4,5,5-tetramethyl-1,3-dioxolan
—— 6-(9-Hydroxynonyl)-2,3-dimethoxy-5-methylphenol 77712-31-3 C18H30O4
6-(9-Hydroxynonyl)-2,3-dimethoxy-5-methylphenol
—— 4,5,6-Trimethyl-pyrogallol 3997-16-8 C9H12O3
4,5,6-Trimethyl-pyrogallol
—— 3-(1-(phenylimino)ethyl)phenol 1318024-44-0 C14H13NO
3-(1-(phenylimino)ethyl)phenol
—— Propanedinitrile, [(2,5-dihydroxyphenyl)methylene]- 143049-24-5 C10H6N2O2
Propanedinitrile, [(2,5-dihydroxyphenyl)methylene]-
—— 4-Methoxy-2-phenethylaminomethyl-phenol 93027-32-8 C16H19NO2
4-Methoxy-2-phenethylaminomethyl-phenol
—— Methyl-2-(o-hydroxyphenyl)-propanoat 54493-89-9 C10H12O3
Methyl-2-(o-hydroxyphenyl)-propanoat
—— 4-Methyl-2-phosphinophenol 105865-37-0 C7H9OP
4-Methyl-2-phosphinophenol