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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-cyano-5-(4-hydroxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoic acid 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester 569343-63-1 C21H27NO8
2-cyano-5-(4-hydroxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoic acid 2-[2-(2-methoxyethoxy)ethoxy]ethyl ester
—— 5-<2-Hydroxy-3-methoxy-phenyl>-3-<4-methoxy-phenyl>-2,5-dihydro-isoxazol 29485-31-2 C17H17NO4
5-<2-Hydroxy-3-methoxy-phenyl>-3-<4-methoxy-phenyl>-2,5-dihydro-isoxazol
—— rac-7-(4-hydroxy-3-methoxybenzyl)-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester 1394174-59-4 C20H25NO4S
rac-7-(4-hydroxy-3-methoxybenzyl)-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester
—— N-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]benzamide 342002-66-8 C14H10BrN3O4
N-[(3-bromo-2-hydroxy-5-nitrophenyl)methylideneamino]benzamide
—— 1-acetyl-4,5-dihydro-3-(4-hydroxy-3-methoxyphenyl)-5-(5-nitro-2-furyl)-1H-pyrazole 129303-17-9 C16H15N3O6
1-acetyl-4,5-dihydro-3-(4-hydroxy-3-methoxyphenyl)-5-(5-nitro-2-furyl)-1H-pyrazole
—— obliquol B 1030593-25-9 C20H32O2
obliquol B
—— 15,15,15,35,55-penta-tert-butyl-1(13,53)-6,9,12-trioxa-1,5(1,2),3(1,3)-tribenzenacyclododecaphana-3,5(1,3)-dibenzenacyclohexaphane-12,32,52-triol 1094856-00-4 C59H76O6
15,15,15,35,55-penta-tert-butyl-1(13,53)-6,9,12-trioxa-1,5(1,2),3(1,3)-tribenzenacyclododecaphana-3,5(1,3)-dibenzenacyclohexaphane-12,32,52-triol
—— N'-(2-hydroxy-5-nitrobenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide 41377-58-6 C15H13N3O5
N'-(2-hydroxy-5-nitrobenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide
—— bis(S-methylisothiosemicarbazone)-2,6-diformyl-4-methylphenol 105201-37-4 C13H18N6OS2
bis(S-methylisothiosemicarbazone)-2,6-diformyl-4-methylphenol
—— (4-Hydroxy-3-nitro-phenyl)-[(Z)-methoxyimino]-acetic acid methyl ester 66340-57-6 C10H10N2O6
(4-Hydroxy-3-nitro-phenyl)-[(Z)-methoxyimino]-acetic acid methyl ester
—— 1299830-95-7 C21H18N4O9
—— 1398523-48-2 C15H12BrClN2O
—— 4,5-dichloro-2-methyl-6-nitrophenol 82598-58-1 C7H5Cl2NO3
4,5-dichloro-2-methyl-6-nitrophenol
—— [(1,3-bis(1-adamantylamide)-2,2-dimethylpropane(-2H))2Zr(CH2Ph)2(THF)] 1239604-77-3 C45H62N2O3Zr
[(1,3-bis(1-adamantylamide)-2,2-dimethylpropane(-2H))2Zr(CH2Ph)2(THF)]
—— 631862-79-8 C9H11NO3
—— diethyl 4-hydroxy-3,5-dimethylphenyl phosphate 1420992-05-7 C12H19O5P
diethyl 4-hydroxy-3,5-dimethylphenyl phosphate
—— N-ethyl-4-(2-hydroxyphenyl)butanamide 898562-42-0 C12H17NO2
N-ethyl-4-(2-hydroxyphenyl)butanamide
—— 3-(1'-Methyl-allyl)-5,6,7,8-tetrahydronaphthol-(2) 13052-32-9 C14H18O
3-(1'-Methyl-allyl)-5,6,7,8-tetrahydronaphthol-(2)
—— p-Hydroxy-benzaldehyd-dibenzylmercaptal 32188-46-8 C21H20OS2
p-Hydroxy-benzaldehyd-dibenzylmercaptal
—— 6-bromo-3-methoxy-2,4-dimethylphenol 1349842-72-3 C9H11BrO2
6-bromo-3-methoxy-2,4-dimethylphenol
—— 5-Methoxy-2-<3-chlor-2-hydroxy-propyloxy>-phenol 103324-53-4 C10H13ClO4
5-Methoxy-2-<3-chlor-2-hydroxy-propyloxy>-phenol
—— bis(isonicotinamidosalicylaldimine)diiododioxouranium(VI) 155642-13-0 C26H22I2N6O6U
bis(isonicotinamidosalicylaldimine)diiododioxouranium(VI)
—— 3-hydroxy-1-propyl-pyridinium; picrate 109126-33-2 C6H2N3O7*C8H12NO
3-hydroxy-1-propyl-pyridinium; picrate
—— 5-bromo-2-hydroxybenzaldehyde O-benzyl oxime 901535-15-7 C14H12BrNO2
5-bromo-2-hydroxybenzaldehyde O-benzyl oxime
—— 2-hydroxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid 1132076-41-5 C9H8O3
2-hydroxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid
—— 1481718-30-2 C11H12N4O4S
—— 3-Hydroxy-9,10-seco-1,3,5(10)-androstatrien-17-on (9,10-seco-10-methyl-oestron) 4787-56-8 C19H26O2
3-Hydroxy-9,10-seco-1,3,5(10)-androstatrien-17-on (9,10-seco-10-methyl-oestron)
—— 910638-61-8 C20H25NO3S
—— [Eu(N,N'-bis[(6-carboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6(-2H))](1+) 1162111-57-0 C26H34EuN4O8
[Eu(N,N'-bis[(6-carboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6(-2H))](1+)
—— 4-[(4-ethoxy-phenylimino)-methyl]-2-methoxy-phenol 58285-73-7 C16H17NO3
4-[(4-ethoxy-phenylimino)-methyl]-2-methoxy-phenol
—— 2-Amino-4,6-difluorophenol hydrochloride 192583-00-9 C6H6ClF2NO
2-Amino-4,6-difluorophenol hydrochloride
—— (2,5-dihydroxy-4-methoxy-phenyl)-(2,4-dinitro-phenylhydrazono)-acetic acid ethyl ester 102027-08-7 C17H16N4O9
(2,5-dihydroxy-4-methoxy-phenyl)-(2,4-dinitro-phenylhydrazono)-acetic acid ethyl ester
—— 1-[4,6-diamino-1-(4-hydroxy-phenyl)-2-methyl-1,2-dihydro-[1,3,5]triazin-2-yl]-2-methyl-propan-2-ol 100879-72-9 C14H21N5O2
1-[4,6-diamino-1-(4-hydroxy-phenyl)-2-methyl-1,2-dihydro-[1,3,5]triazin-2-yl]-2-methyl-propan-2-ol
—— vanillin-(6-methoxy-2,5-dimethyl-pyrimidin-4-ylhydrazone) 101087-60-9 C15H18N4O3
vanillin-(6-methoxy-2,5-dimethyl-pyrimidin-4-ylhydrazone)
—— 91428-64-7 C5H11N*C6H5ClO
—— 3-Nitro-4-hydroxy-ω-cinnamyliden-acetophenon 109090-69-9 C17H13NO4
3-Nitro-4-hydroxy-ω-cinnamyliden-acetophenon
—— 2-methoxy-4-methylphen-3,5,6-d3-ol 7329-56-8 C8H10O2
2-methoxy-4-methylphen-3,5,6-d3-ol
—— 5-(4-hydroxybenzyl)-3-phytylthiazolidine-2,4-dione 85031-24-9 C30H47NO3S
5-(4-hydroxybenzyl)-3-phytylthiazolidine-2,4-dione
—— 3-(2,4-Dihydroxybenzylidenamino)-pyridin 41082-68-2 C12H10N2O2
3-(2,4-Dihydroxybenzylidenamino)-pyridin
—— 2-Hydroxy-4-methoxy-6-propyl-benzaldehyde 192211-95-3 C11H14O3
2-Hydroxy-4-methoxy-6-propyl-benzaldehyde
—— 887908-37-4 C19H21N5O4
—— acetoxy(2,4-dihydroxy-3-nitrophenyl)mercury 861553-96-0 C8H7HgNO6
acetoxy(2,4-dihydroxy-3-nitrophenyl)mercury
—— 1403585-79-4 C11H13GeN3
—— 2-Hydroxy-5-nitrobenzaldehyde 2-[4-(4-morpholinyl)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]hydrazone 321968-50-7 C18H22N8O4
2-Hydroxy-5-nitrobenzaldehyde 2-[4-(4-morpholinyl)-6-(1-pyrrolidinyl)-1,3,5-triazin-2-yl]hydrazone
—— 4-((4-hydroxybenzylidene)amino)-3-thioxo-1,2,4-triazinan-5-one 1254335-86-8 C10H10N4O2S
4-((4-hydroxybenzylidene)amino)-3-thioxo-1,2,4-triazinan-5-one
—— 4-(2-Amino-4-dimethylamino-phenylamino)-2,6-dimethyl-phenol 41669-54-9 C16H21N3O
4-(2-Amino-4-dimethylamino-phenylamino)-2,6-dimethyl-phenol
—— 2-anilino-hydroquinone 121565-48-8 C12H11NO2
2-anilino-hydroquinone
—— 2-methoxy-4-(4,6,6-trimethyl-5,6-dihydro-2<i>H</i>-[1,3]thiazin-2-yl)-phenol 109601-76-5 C14H19NO2S
2-methoxy-4-(4,6,6-trimethyl-5,6-dihydro-2<i>H</i>-[1,3]thiazin-2-yl)-phenol
—— 3,4,5-trihydroxyphenethyl ethanoate 1375102-38-7 C10H12O6
3,4,5-trihydroxyphenethyl ethanoate
—— Tetrahydroxy-o-xylol 34785-90-5 C8H10O4
Tetrahydroxy-o-xylol