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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-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanon 4899-73-4 C10H12O4
2-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanon
—— 1-(4-(2-(Cyclohexylmethoxy)ethyl)phenoxy)-3-isopropylaminopropan-2-ol hydrochloride 63659-41-6 C21H36ClNO3
1-(4-(2-(Cyclohexylmethoxy)ethyl)phenoxy)-3-isopropylaminopropan-2-ol hydrochloride
—— 2-(3-methoxy-4-hydroxyphenyl)1,3-dinitropropane 6178-43-4 C10H12N2O6
2-(3-methoxy-4-hydroxyphenyl)1,3-dinitropropane
—— 2-[2-(4-Hydroxy-3-methoxy-phenyl)-1-hydroxymethyl-ethyl]-6-methoxy-indan-1,5-diol 104086-80-8 C20H24O6
2-[2-(4-Hydroxy-3-methoxy-phenyl)-1-hydroxymethyl-ethyl]-6-methoxy-indan-1,5-diol
—— 5-methoxybenzene-1,2,4-triol 74202-09-8 C7H8O4
5-methoxybenzene-1,2,4-triol
—— 2-Chloro-4,5-dihydroxymandelic acid 96657-18-0 C8H7ClO5
2-Chloro-4,5-dihydroxymandelic acid
—— 5-Hydroxy-2,3,4-trimethoxy-benzaldehyde 127581-57-1 C10H12O5
5-Hydroxy-2,3,4-trimethoxy-benzaldehyde
—— 2-Methoxy-p-nitrosophenol 19628-78-5 C7H7NO3
2-Methoxy-p-nitrosophenol
—— trans,trans-bis<3-(4-hydroxy-3-methoxyphenyl)-2-propenyl> sulfide 68946-35-0 C20H22O4S
trans,trans-bis<3-(4-hydroxy-3-methoxyphenyl)-2-propenyl> sulfide
—— 4-acetyl-5-(4-hydroxy-3,5-dimethoxyphanyl)-3,4-dihydrofuran-2(5H)-one 287729-39-9 C14H16O6
4-acetyl-5-(4-hydroxy-3,5-dimethoxyphanyl)-3,4-dihydrofuran-2(5H)-one
—— 5-(2-methoxyphenyl)-1-(4'-hydroxy-3',5'-dimethoxyphenyl)-2,4-pentadien-1-one 1356939-69-9 C20H20O5
5-(2-methoxyphenyl)-1-(4'-hydroxy-3',5'-dimethoxyphenyl)-2,4-pentadien-1-one
—— N-[4-(4-Hydroxy-3,5-dimethoxy-phenyl)-thiazol-2-yl]-oxalamic acid ethyl ester 74604-60-7 C15H16N2O6S
N-[4-(4-Hydroxy-3,5-dimethoxy-phenyl)-thiazol-2-yl]-oxalamic acid ethyl ester
—— 2,6-dimethoxy-4-(1-methoxyethyl)phenol 1105671-50-8 C11H16O4
2,6-dimethoxy-4-(1-methoxyethyl)phenol
—— N-(5-ethylpyrazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide 948573-56-6 C14H17N3O3
N-(5-ethylpyrazol-3-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide
—— 4-(3-hydroxyprop-1-yn-1-yl)-2-methoxyphenol 1486420-55-6 C10H10O3
4-(3-hydroxyprop-1-yn-1-yl)-2-methoxyphenol
—— 3-Methoxy-4-(2nitrovinyl)phenol 4230-92-6 C9H9NO4
3-Methoxy-4-(2nitrovinyl)phenol
—— 4-(adamantan-1-ylaminomethyl)-3-methoxyphenol 1427505-41-6 C18H25NO2
4-(adamantan-1-ylaminomethyl)-3-methoxyphenol
—— 3-methoxy-4-(pyrrolidin-1-ylmethyl)phenol 917828-11-6 C12H17NO2
3-methoxy-4-(pyrrolidin-1-ylmethyl)phenol
—— 4-Bromo-6-tert-butyl-2-methoxyphenol 168985-93-1 C11H15BrO2
4-Bromo-6-tert-butyl-2-methoxyphenol
—— 2-amino-3-cyano-4-(3-iodo-4-hydroxy-5-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran 524686-71-3 C19H19IN2O4
2-amino-3-cyano-4-(3-iodo-4-hydroxy-5-methoxyphenyl)-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran
—— 2-bromo-3,4-dihydroxy-5-methoxybenzaldehyde 65144-12-9 C8H7BrO4
2-bromo-3,4-dihydroxy-5-methoxybenzaldehyde
—— 2-Iodo-6-methoxy-4-[(E)-p-tolylimino-methyl]-phenol 245542-29-4 C15H14INO2
2-Iodo-6-methoxy-4-[(E)-p-tolylimino-methyl]-phenol
—— trans-3-(4-hydroxy-3-methoxyphenyl)-2-propenylthiol 74953-25-6 C10H12O2S
trans-3-(4-hydroxy-3-methoxyphenyl)-2-propenylthiol
—— isonicotinic acid N2-(3-iodo-4-hydroxy-5-methoxybenzylidene)hydrazide 92160-56-0 C14H12IN3O3
isonicotinic acid N2-(3-iodo-4-hydroxy-5-methoxybenzylidene)hydrazide
—— 1,1'-((4-((3,4-dimethoxybenzyl)amino)-8-((4-hydroxy-3-methoxybenzyl)amino)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanediyl))bis(propan-2-ol) 1280167-90-9 C29H38N8O6
1,1'-((4-((3,4-dimethoxybenzyl)amino)-8-((4-hydroxy-3-methoxybenzyl)amino)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanediyl))bis(propan-2-ol)
—— 5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione 73681-09-1 C12H9IN2O4S
5-(4-hydroxy-3-iodo-5-methoxybenzylidene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
—— 4-(Hydroxymethyl)-2-methoxy-6-pentylphenol 1448251-91-9 C13H20O3
4-(Hydroxymethyl)-2-methoxy-6-pentylphenol
—— 2,6-dichloro-5-hydroxyvanillin 76330-07-9 C8H6Cl2O4
2,6-dichloro-5-hydroxyvanillin
—— 5-Iod-vanillin-octadecylthiosemicarbazon 6958-25-4 C27H46IN3O2S
5-Iod-vanillin-octadecylthiosemicarbazon
—— 2,6-Dimethyl-4-((E)-2-pyridin-2-yl-vinyl)-phenol 127063-64-3 C15H15NO
2,6-Dimethyl-4-((E)-2-pyridin-2-yl-vinyl)-phenol
—— 1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazol-1-yl)ethanone 1472645-97-8 C18H18FN3O3
1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-(4-fluorophenyl)-4,5-dihydropyrazol-1-yl)ethanone
—— diethyl 2-hydroxy-5-methylphenyl phosphonate 83110-01-4 C11H17O4P
diethyl 2-hydroxy-5-methylphenyl phosphonate
—— 1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-(2-bromophenyl)-4,5-dihydropyrazol-1-yl)ethanone 1472645-98-9 C18H18BrN3O3
1-(5-(3-amino-4-hydroxy-5-methoxyphenyl)-3-(2-bromophenyl)-4,5-dihydropyrazol-1-yl)ethanone
—— 2-(2,2-bis(trifluoromethylsulfonyl)ethyl)-6-bromo-4-methylphenol 1360543-99-2 C11H9BrF6O5S2
2-(2,2-bis(trifluoromethylsulfonyl)ethyl)-6-bromo-4-methylphenol
—— N-phenethyl-N-propyl-3,4-dihydroxyphenethylamine hydrochloride 63925-50-8 C19H25NO2*ClH
N-phenethyl-N-propyl-3,4-dihydroxyphenethylamine hydrochloride
—— (E)-2-(2-hydroxyphenyl)acetaldehyde oxime 1438253-42-9 C8H9NO2
(E)-2-(2-hydroxyphenyl)acetaldehyde oxime
—— 2-allyloxyimino-2-(3-hydroxyphenyl)acetic acid 66340-61-2 C11H11NO4
2-allyloxyimino-2-(3-hydroxyphenyl)acetic acid
—— N-(3,5-dibromo-4-hydroxyphenethyl)acrylamide 1260376-38-2 C11H11Br2NO2
N-(3,5-dibromo-4-hydroxyphenethyl)acrylamide
—— 4-Pentyl-o-cresol 23595-48-4 C12H18O
4-Pentyl-o-cresol
—— 4-Pentyl-m-cresol 23595-49-5 C12H18O
4-Pentyl-m-cresol
—— Phenol, butyltetrachloro- 64059-31-0 C10H10Cl4O
Phenol, butyltetrachloro-
—— 3-[1-(5-chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester 1354060-48-2 C15H17ClN2O3
3-[1-(5-chloro-2-hydroxy-benzyl)-5-methyl-1H-pyrazol-3-yl]-propionic acid methyl ester
—— 2-aminomethyl-4-nitro-phenol; hydrochloride 113186-97-3 C7H8N2O3*ClH
2-aminomethyl-4-nitro-phenol; hydrochloride
—— 4-(2-Hydroxy-3-nitrobenzoyl)morpholine-3-carboxylic acid 473730-81-3 C12H12N2O7
4-(2-Hydroxy-3-nitrobenzoyl)morpholine-3-carboxylic acid
—— Morpholine, 4-(3,4-dimethoxy-5-hydroxybenzoyl)- 65133-72-4 C13H17NO5
Morpholine, 4-(3,4-dimethoxy-5-hydroxybenzoyl)-
—— [Difluoro-(4-hydroxy-phenyl)-methyl]-phosphonic acid diethyl ester 181188-33-0 C11H15F2O4P
[Difluoro-(4-hydroxy-phenyl)-methyl]-phosphonic acid diethyl ester
—— 2-bromo-4-(3-hydroxy-4-methylpentyl)phenol 360578-02-5 C12H17BrO2
2-bromo-4-(3-hydroxy-4-methylpentyl)phenol
—— 2-bromo-4-(3-hydroxy-5-methylhexyl)phenol 360578-03-6 C13H19BrO2
2-bromo-4-(3-hydroxy-5-methylhexyl)phenol
—— 1-acetyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine 94427-36-8 C13H15NO3
1-acetyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
—— 1-acetyl-4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine 94427-34-6 C14H17NO3
1-acetyl-4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine