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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
—— (Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-cyclopentylimino-3-phenyl-thiazolidin-4-one 1228116-84-4 C21H19ClN2O2S
(Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-cyclopentylimino-3-phenyl-thiazolidin-4-one
—— 4-[2-(dimethylamino)ethyl]benzene-1,2-diol;hydron;chloride —— C10H16ClNO2
4-[2-(dimethylamino)ethyl]benzene-1,2-diol;hydron;chloride
—— 4-[4-(aminomethyl)hepta-1,6-dien-4-yl]phenol;hydron;chloride —— C14H20ClNO
4-[4-(aminomethyl)hepta-1,6-dien-4-yl]phenol;hydron;chloride
—— (Z,Z)-3-benzyl-5-(3-chloro-4-hydroxy-benzylidene)-2-isopropylimino-thiazolidin-4-one 1228117-06-3 C20H19ClN2O2S
(Z,Z)-3-benzyl-5-(3-chloro-4-hydroxy-benzylidene)-2-isopropylimino-thiazolidin-4-one
—— (Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-cyclohexylimino-3-phenyl-thiazolidin-4-one 1228116-85-5 C22H21ClN2O2S
(Z,Z)-5-(3-chloro-4-hydroxybenzylidene)-2-cyclohexylimino-3-phenyl-thiazolidin-4-one
—— (Z,Z)-3-[5-(3-chloro-4-hydroxybenzylidene)-2-isopropylimino-4-oxo-thiazolidin-3-yl]-propionic acid ethyl ester 1228116-89-9 C18H21ClN2O4S
(Z,Z)-3-[5-(3-chloro-4-hydroxybenzylidene)-2-isopropylimino-4-oxo-thiazolidin-3-yl]-propionic acid ethyl ester
—— 1,2-Benzenediol, 4-(2-((phenylmethyl)amino)ethyl)-, hydrochloride 13075-94-0 C15H18ClNO2
1,2-Benzenediol, 4-(2-((phenylmethyl)amino)ethyl)-, hydrochloride
—— AD284a 581800-17-1 C16H18O5
AD284a
—— 1-ethyl-4-(4-hydroxy-3-methoxy-<i>trans</i>-styryl)-pyridinium; bromide 6266-18-8 Br*C16H18NO2
1-ethyl-4-(4-hydroxy-3-methoxy-<i>trans</i>-styryl)-pyridinium; bromide
—— (R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(3-fluoro-4-hydroxyphenyl)oxazolidin-2-one 1025097-59-9 C16H24FNO4Si
(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(3-fluoro-4-hydroxyphenyl)oxazolidin-2-one
—— 1-amino-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol 95586-81-5 C12H19NO3
1-amino-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol
—— 1-amino-3-(4-(2-hydroxyethyl)phenoxy)propan-2-ol 1021935-61-4 C11H17NO3
1-amino-3-(4-(2-hydroxyethyl)phenoxy)propan-2-ol
—— 3,5,3',4',5'-Pentamethoxy-biphenyl-4-ol 101747-56-2 C17H20O6
3,5,3',4',5'-Pentamethoxy-biphenyl-4-ol
—— 5-[(6-(benzyloxy)-2-hydroxy-3-methoxyphenyl)(hydroxy)methyl]-4-hydroxy-3-phenylfuran-2(5H)-one 1247734-10-6 C25H22O7
5-[(6-(benzyloxy)-2-hydroxy-3-methoxyphenyl)(hydroxy)methyl]-4-hydroxy-3-phenylfuran-2(5H)-one
—— 6-(benzyloxy)-2-hydroxy-3-methoxybenzaldehyde 1247734-31-1 C15H14O4
6-(benzyloxy)-2-hydroxy-3-methoxybenzaldehyde
—— 2-(benzyloxy)-6-hydroxy-3-methoxybenzaldehyde 1247734-44-6 C15H14O4
2-(benzyloxy)-6-hydroxy-3-methoxybenzaldehyde
—— (E)-2-hydroxy-4,6-dimethoxystyryl-4-chlorobenzylsulfone 334969-49-2 C17H17ClO5S
(E)-2-hydroxy-4,6-dimethoxystyryl-4-chlorobenzylsulfone
—— 3-[penta-deca-8,11-dienyl]phenol 51546-63-5 C21H32O
3-[penta-deca-8,11-dienyl]phenol
—— 2-{[(3-chloro-5-(trifluoromethyl)pyridin-2-yl)imino]methyl}-phenol 303090-94-0 C13H8ClF3N2O
2-{[(3-chloro-5-(trifluoromethyl)pyridin-2-yl)imino]methyl}-phenol
—— 2-(2-Hydroxy-phenyl)-propionitrile 88975-44-4 C9H9NO
2-(2-Hydroxy-phenyl)-propionitrile
—— 5-hydroxy-2-nitrobenzamide 4315-16-6 C7H6N2O4
5-hydroxy-2-nitrobenzamide
—— 1-deazapyridoxine 42760-56-5 C9H12O3
1-deazapyridoxine
—— 4-(2-(pyridin-4-yl)ethynyl)phenol 898564-30-2 C13H9NO
4-(2-(pyridin-4-yl)ethynyl)phenol
—— [4-13C]-4,6-dibromo-2,3-dimethylphenol 476170-66-8 C8H8Br2O
[4-13C]-4,6-dibromo-2,3-dimethylphenol
—— 3-(2-methoxy-4-hydroxybenzylidene)anabaseine 248270-40-8 C18H18N2O2
3-(2-methoxy-4-hydroxybenzylidene)anabaseine
—— [1-13C]-2,3-dimethylphenol 476170-56-6 C8H10O
[1-13C]-2,3-dimethylphenol
—— 3,5-dibutyl-4-hydroxytoluene 720-39-8 C15H24O
3,5-dibutyl-4-hydroxytoluene
—— [4-13C]-2,3-dimethylphenol 476170-67-9 C8H10O
[4-13C]-2,3-dimethylphenol
—— 5-benzyloxy-3-bromo-2-hydroxybenzaldehyde 647858-58-0 C14H11BrO3
5-benzyloxy-3-bromo-2-hydroxybenzaldehyde
—— (S)-(+)-2-(4-hydroxyphenyl)propionic acid ethoxycarbonylmethylester 164210-40-6 C13H16O5
(S)-(+)-2-(4-hydroxyphenyl)propionic acid ethoxycarbonylmethylester
—— (<i>S</i>)-2-(4-hydroxy-phenyl)-propionic acid methyl ester 124508-78-7 C10H12O3
(<i>S</i>)-2-(4-hydroxy-phenyl)-propionic acid methyl ester
—— spoxazomicin C 1337978-34-3 C10H11NO3
spoxazomicin C
—— 2-allyl-4-[(tert-butyl(dimethyl)silyloxy)methyl]phenol 137314-07-9 C16H26O2Si
2-allyl-4-[(tert-butyl(dimethyl)silyloxy)methyl]phenol
—— 4-Hexyl-2-(N-(o-hydroxyphenyl)formimidoyl)phenol 16704-09-9 C19H23NO2
4-Hexyl-2-(N-(o-hydroxyphenyl)formimidoyl)phenol
—— 5-chloro-2-hydroxyphenyl isocyanate 122020-63-7 C7H4ClNO2
5-chloro-2-hydroxyphenyl isocyanate
—— 2-(4,5-dihydrooxazol-2-yl)-5-methylphenol 24201-15-8 C10H11NO2
2-(4,5-dihydrooxazol-2-yl)-5-methylphenol
—— 3-(4-hydroxy-2-methoxyphenyl)propanol 106800-27-5 C10H14O3
3-(4-hydroxy-2-methoxyphenyl)propanol
—— 2-(4-hydroxy-2-methylphenyl)-2-methyl-1,3-dioxolane 1171247-69-0 C11H14O3
2-(4-hydroxy-2-methylphenyl)-2-methyl-1,3-dioxolane
—— 4-methoxy-2-(methoxymethoxy)phenol 123913-92-8 C9H12O4
4-methoxy-2-(methoxymethoxy)phenol
—— 3-(2-hydroxy-4-methoxyphenyl)propanol 106800-26-4 C10H14O3
3-(2-hydroxy-4-methoxyphenyl)propanol
—— (2-Fluoro-4-hydroxy-benzyl)-carbamic acid tert-butyl ester 392636-92-9 C12H16FNO3
(2-Fluoro-4-hydroxy-benzyl)-carbamic acid tert-butyl ester
—— 5-(adamantan-1-ylaminomethyl)-2-methoxyphenol 1019579-53-3 C18H25NO2
5-(adamantan-1-ylaminomethyl)-2-methoxyphenol
—— 3-methyl-4-methoxy-1,2-dihydroxybenzene 77357-51-8 C8H10O3
3-methyl-4-methoxy-1,2-dihydroxybenzene
—— 5-isopropoxy-2,4-dimethoxy-3-methylphenol 105104-02-7 C12H18O4
5-isopropoxy-2,4-dimethoxy-3-methylphenol
—— 4-(4-hydroxy-3-methoxyphenyl)-2-methylenebutyrolactone 1447662-19-2 C12H12O4
4-(4-hydroxy-3-methoxyphenyl)-2-methylenebutyrolactone
—— 2,4,5-trimethoxy-3-methylphenol 105104-01-6 C10H14O4
2,4,5-trimethoxy-3-methylphenol
—— p-tert-butylcalix[5]PNMe2(OH)3 202530-58-3 C57H74NO5P
p-tert-butylcalix[5]PNMe2(OH)3
—— (1S,4S,5R,6R)-4-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-2-oxo-6-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester 641627-93-2 C34H50N2O7Si
(1S,4S,5R,6R)-4-(5-Hydroxy-2,4-dimethoxy-3-methyl-benzyl)-2-oxo-6-triisopropylsilanyloxymethyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester
—— 5-(2-acetoxyethyl)-2-(benzyloxy)benzoic acid 1237517-67-7 C18H18O5
5-(2-acetoxyethyl)-2-(benzyloxy)benzoic acid
—— 6-(4-hydroxyphenyl)hexan-2-one 169334-30-9 C12H16O2
6-(4-hydroxyphenyl)hexan-2-one