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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-<2-(3,4,5-trimethoxy-phenyl)-aethoxy>-carbamidsaeure-aethylester 101777-47-3 C14H21NO6
N-<2-(3,4,5-trimethoxy-phenyl)-aethoxy>-carbamidsaeure-aethylester
—— Acetic acid 2,3-dichloro-6-hydroxy-5-nitro-benzyl ester 39554-71-7 C9H7Cl2NO5
Acetic acid 2,3-dichloro-6-hydroxy-5-nitro-benzyl ester
—— (3S,4S,5R)-3,4-dihydroxy-1,3-dimethyl-5-[(4-phenylmethoxyphenyl)methyl]pyrrolidin-2-one 1370332-35-6 C20H23NO4
(3S,4S,5R)-3,4-dihydroxy-1,3-dimethyl-5-[(4-phenylmethoxyphenyl)methyl]pyrrolidin-2-one
—— 2-chloro-6-(1-hydroxyallyl)phenol 911817-91-9 C9H9ClO2
2-chloro-6-(1-hydroxyallyl)phenol
—— N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-phenylacetamide 92966-75-1 C16H16N2O3
N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-phenylacetamide
—— 4-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-5-isopropyl-4,5-dihydroisoxazol-5-yl}phenol 809238-55-9 C20H33NO3Si
4-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-5-isopropyl-4,5-dihydroisoxazol-5-yl}phenol
—— 2-(2-hydroxyphenyl)-2-propyl-1-pentanol 204266-13-7 C14H22O2
2-(2-hydroxyphenyl)-2-propyl-1-pentanol
—— 1-(2,6-dihydroxyphenyl)-2-methyl-1-propanone oxime 1380697-40-4 C10H13NO3
1-(2,6-dihydroxyphenyl)-2-methyl-1-propanone oxime
—— 3-(2.5-Dihydroxy-phenyl)-5-(3.4-dimethoxy-phenyl)isooxazol 19743-25-0 C17H15NO5
3-(2.5-Dihydroxy-phenyl)-5-(3.4-dimethoxy-phenyl)isooxazol
—— N(3-methylthiopropyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide 276702-72-8 C10H13ClN2O5S2
N(3-methylthiopropyl)-6-chloro-2-hydroxy-3-nitrobenzenesulfonamide
—— 3-bromo-4-hydroxy-5-(trimethylsilyl)phenethyl methanesulfonate 1127943-65-0 C12H19BrO4SSi
3-bromo-4-hydroxy-5-(trimethylsilyl)phenethyl methanesulfonate
—— 91328-87-9 C9H13N3O3
—— 2,2'-((1E,1'E)-((2-((benzyloxy)methyl)-2-((((E)-6-hydroxy-2,3,4-trimethoxybenzylidene)amino)methyl)propane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(3,4,5-trimethoxyphenol) 131626-89-6 C42H51N3O13
2,2'-((1E,1'E)-((2-((benzyloxy)methyl)-2-((((E)-6-hydroxy-2,3,4-trimethoxybenzylidene)amino)methyl)propane-1,3-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(3,4,5-trimethoxyphenol)
—— N'-(5-hydroxy-2-nitrobenzylidene)thiophene-2-carbohydrazide 328586-43-2 C12H9N3O4S
N'-(5-hydroxy-2-nitrobenzylidene)thiophene-2-carbohydrazide
—— 3,5-dibromo-2-hydroxyacetophenone oxime 99799-48-1 C8H7Br2NO2
3,5-dibromo-2-hydroxyacetophenone oxime
—— 2-hydroxy-5-bromotrimethylanilinium iodide 114960-01-9 C9H13BrNO*I
2-hydroxy-5-bromotrimethylanilinium iodide
—— 2-bromo-6-methoxy-3-((Z)-2-methoxyvinyl)phenol 1448888-81-0 C10H11BrO3
2-bromo-6-methoxy-3-((Z)-2-methoxyvinyl)phenol
—— 3-(2-hydroxyphenyl)-5,5-dimethyltetrahydrofuran-2-ol 398454-32-5 C12H16O3
3-(2-hydroxyphenyl)-5,5-dimethyltetrahydrofuran-2-ol
—— (E)-2-((1-hydroxy-2-methylpropan-2-ylimino)methyl)-4-nitrophenol 1350842-45-3 C11H14N2O4
(E)-2-((1-hydroxy-2-methylpropan-2-ylimino)methyl)-4-nitrophenol
—— 4,6-bis[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1-(2-morpholin-4-ylethyl)pyrimidine-2-thione 1551600-87-3 C28H31N3O5S
4,6-bis[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1-(2-morpholin-4-ylethyl)pyrimidine-2-thione
—— 2,5-dibromo-3,6-dimethoxy-hydroquinone 34602-76-1 C8H8Br2O4
2,5-dibromo-3,6-dimethoxy-hydroquinone
—— (+/-)-isoretronecanol picrate 23179-28-4 C6H3N3O7*C8H15NO
(+/-)-isoretronecanol picrate
—— 4-Iod-2-methoxy-5-(2-nitro-vinyl)-phenol 7413-12-9 C9H8INO4
4-Iod-2-methoxy-5-(2-nitro-vinyl)-phenol
—— 2-(benzyl-14-crown-4)phenol 106419-85-6 C24H32O5
2-(benzyl-14-crown-4)phenol
—— 2-Methoxy-4-(1-<sup>14</sup>C-acetyl)-phenol 15212-04-1 C9H10O3
2-Methoxy-4-(1-<sup>14</sup>C-acetyl)-phenol
—— Acetyl-di-O-methyl-dihydroxy-thujaplicatin-methylaether 13594-89-3 C25H30O10
Acetyl-di-O-methyl-dihydroxy-thujaplicatin-methylaether
—— 1-[5-(4-Hydroxy-3-methoxy-phenyl)-3-(4-{[1-(1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone 114217-19-5 C27H24N4O3
1-[5-(4-Hydroxy-3-methoxy-phenyl)-3-(4-{[1-(1H-indol-3-yl)-meth-(E)-ylidene]-amino}-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone
—— 3,4,5-trihydroxy-benzoic acid-(N'-phenyl-hydrazide) 129324-82-9 C13H12N2O4
3,4,5-trihydroxy-benzoic acid-(N'-phenyl-hydrazide)
—— tert-butyl 2-(4-hydroxy-3-methoxybenzyl)acrylate 1146623-01-9 C15H20O4
tert-butyl 2-(4-hydroxy-3-methoxybenzyl)acrylate
—— 4-{2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}phenol 944335-20-0 C13H18O3
4-{2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}phenol
—— [(4-Hydroxy-3,5-diiodo-benzimidoyl)-aminooxy]-acetic acid ethyl ester 63409-77-8 C11H12I2N2O4
[(4-Hydroxy-3,5-diiodo-benzimidoyl)-aminooxy]-acetic acid ethyl ester
—— 2-Azetidinemethanesulfonamide, N-[(3-hydroxyphenyl)methyl]- 1897738-23-6 C11H16N2O3S
2-Azetidinemethanesulfonamide, N-[(3-hydroxyphenyl)methyl]-
—— 28006-97-5 C10H12BrN3O4
—— (2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol 1292847-81-4 C18H24O5
(2S,4R,4aR,8R,8aR)-2-(4-hydroxy-3-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8, 8a-hexahydro-2H-chromene-4,8-diol
—— 2-(1-(1H-pyrrol-2-yl)ethyl)phenol 1295507-39-9 C12H13NO
2-(1-(1H-pyrrol-2-yl)ethyl)phenol
—— 3-Bromo-2-hydroxy-6-methoxy-4-phenylmethoxybenzaldehyde 1256914-56-3 C15H13BrO4
3-Bromo-2-hydroxy-6-methoxy-4-phenylmethoxybenzaldehyde
—— ethyl 5-(2-hydroxyphenyl)-3-methylisooxazole-4-carboxylate 92397-18-7 C13H13NO4
ethyl 5-(2-hydroxyphenyl)-3-methylisooxazole-4-carboxylate
—— 4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)phenol 522609-22-9 C17H11F17O
4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)phenol
—— 3,5-Dinitro-4-hydroxy-benzyliden-malodinitril 80589-34-0 C10H4N4O5
3,5-Dinitro-4-hydroxy-benzyliden-malodinitril
—— 3-(3-hydroxybutyl)-4-(4-hydroxybenzylidene)amino-1H-1,2,4-triazole-5-thione 1192035-24-7 C13H16N4O2S
3-(3-hydroxybutyl)-4-(4-hydroxybenzylidene)amino-1H-1,2,4-triazole-5-thione
—— 3.5.Dibrom-2'.4'.6'-trichlorthionosalicylsaeureanilid 23239-02-3 C13H6Br2Cl3NOS
3.5.Dibrom-2'.4'.6'-trichlorthionosalicylsaeureanilid
—— 2,5-dihydroxy-3,6-bis-(2-hydroxybenzyl)pyrazine 81077-88-5 C18H16N2O4
2,5-dihydroxy-3,6-bis-(2-hydroxybenzyl)pyrazine
—— Benzeneacetic acid, I+/-,2-dihydroxy-3-(trifluoromethoxy)- 1261554-42-0 C9H7F3O5
Benzeneacetic acid, I+/-,2-dihydroxy-3-(trifluoromethoxy)-
—— 2,2'-((butane-1,4-diylbis(azaneylylidene))bis(methaneylylidene))bis(4-nitrophenol) 1204603-99-5 C18H18N4O6
2,2'-((butane-1,4-diylbis(azaneylylidene))bis(methaneylylidene))bis(4-nitrophenol)
—— 2,4,6-D3-Resorcin 124286-10-8 C6H6O2
2,4,6-D3-Resorcin
—— (5-amino-4-hydroxy-2-methoxy-phenyl)-arsonic acid 861527-94-8 C7H10AsNO5
(5-amino-4-hydroxy-2-methoxy-phenyl)-arsonic acid
—— 2-Methoxy-4-[2-(3-methyl-1,2-thiazol-5-yl)ethenyl]phenol 131068-29-6 C13H13NO2S
2-Methoxy-4-[2-(3-methyl-1,2-thiazol-5-yl)ethenyl]phenol
—— 3,5-Dichloro-4-ethyl-2,6-dimethoxyphenol 108545-02-4 C10H12Cl2O3
3,5-Dichloro-4-ethyl-2,6-dimethoxyphenol
—— 1258500-64-9 C19H30O2Si
—— 2-(2-aminocyclohexylamino)-6-(2-hydroxy-3-methoxybenzylamino)-8-azapurine 663889-37-0 C18H24N8O2
2-(2-aminocyclohexylamino)-6-(2-hydroxy-3-methoxybenzylamino)-8-azapurine