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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
—— 4-(2-(dimethylamino)ethoxy)phenol 100238-29-7 C10H15NO2
4-(2-(dimethylamino)ethoxy)phenol
—— 2-trimethylsilyl-1,4-hydroquinone 15288-57-0 C9H14O2Si
2-trimethylsilyl-1,4-hydroquinone
—— 2-[(4-methoxyphenyl)methylideneamino]-5-nitrophenol 29644-87-9 C14H12N2O4
2-[(4-methoxyphenyl)methylideneamino]-5-nitrophenol
—— 2-bromo-4-tetrahydropyranyloxyphenol 201004-82-2 C11H13BrO3
2-bromo-4-tetrahydropyranyloxyphenol
—— 7-Bromo-5-hydroxy-1,3-benzothioxol-2-one 126190-09-8 C7H3BrO3S
7-Bromo-5-hydroxy-1,3-benzothioxol-2-one
—— (-)-isozonarol 250146-75-9 C21H30O2
(-)-isozonarol
—— (-)-ent-zonarol 39707-54-5 C21H30O2
(-)-ent-zonarol
—— 6-Bromo-5-hydroxy-1,3-benzothioxol-2-one 17835-34-6 C7H3BrO3S
6-Bromo-5-hydroxy-1,3-benzothioxol-2-one
—— 4-Bromo-5-hydroxy-1,3-benzothioxol-2-one 126190-10-1 C7H3BrO3S
4-Bromo-5-hydroxy-1,3-benzothioxol-2-one
—— 2-(4-Hydroxyphenyl)-4-(propan-2-yl)-2H-1,4-thiazin-3(4H)-one 87904-90-3 C13H15NO2S
2-(4-Hydroxyphenyl)-4-(propan-2-yl)-2H-1,4-thiazin-3(4H)-one
—— t-butyl N-[2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate 478375-22-3 C18H28BNO5
t-butyl N-[2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate
—— 2,3,5,6-tetrakis-ethylsulfanyl-hydroquinone 100964-28-1 C14H22O2S4
2,3,5,6-tetrakis-ethylsulfanyl-hydroquinone
—— 4-(1-bromoethyl)phenol 59771-02-7 C8H9BrO
4-(1-bromoethyl)phenol
—— (rac)-4-(1-hydroxyethyl)-2-chlorophenol 154639-01-7 C8H9ClO2
(rac)-4-(1-hydroxyethyl)-2-chlorophenol
—— 4-Butoxy-2,5-dimethyl-phenol 147351-63-1 C12H18O2
4-Butoxy-2,5-dimethyl-phenol
—— 2-amino-5-chloro-4-methoxyphenol 98280-37-6 C7H8ClNO2
2-amino-5-chloro-4-methoxyphenol
—— [5-(3-Hydroxy-4-methoxyphenyl)-2-sulfanylidene-1,3,4-thiadiazol-3-yl]-(4-hydroxyphenyl)methanone 1279084-94-4 C16H12N2O4S2
[5-(3-Hydroxy-4-methoxyphenyl)-2-sulfanylidene-1,3,4-thiadiazol-3-yl]-(4-hydroxyphenyl)methanone
—— 3-hydroxy-4-methoxybenzaldehyde 4-hydroxybenzoyl hydrazone 386284-11-3 C15H14N2O4
3-hydroxy-4-methoxybenzaldehyde 4-hydroxybenzoyl hydrazone
—— n-butyl, 3,4-dihydroxy-5-nitrophenylglyoxylate 125629-05-2 C12H13NO7
n-butyl, 3,4-dihydroxy-5-nitrophenylglyoxylate
—— dimethyl 4-hydroxy-2-methoxyphenyl phosphate 94420-80-1 C9H13O6P
dimethyl 4-hydroxy-2-methoxyphenyl phosphate
—— (2S)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one 1360617-34-0 C16H22O4
(2S)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one
—— 2,3a,4,5-Tetrahydro-6-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-3H-indazol-3-one 111570-61-7 C22H22N2O5
2,3a,4,5-Tetrahydro-6-(2-hydroxy-4,6-dimethoxyphenyl)-4-(4-methoxyphenyl)-3H-indazol-3-one
—— (2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one 1360617-33-9 C16H22O4
(2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexan-1-one
—— 2-allyl-6-methoxybenzene-1,4-diol 31788-39-3 C10H12O3
2-allyl-6-methoxybenzene-1,4-diol
—— 3-Methoxy-4-methoxymethoxyphenol 104202-49-5 C9H12O4
3-Methoxy-4-methoxymethoxyphenol
—— 4-(1-aminoethyl)-2-methoxyphenol —— C9H13NO2
4-(1-aminoethyl)-2-methoxyphenol
—— 4-[(Butylamino)methyl]-2-methoxyphenol 112520-76-0 C12H19NO2
4-[(Butylamino)methyl]-2-methoxyphenol
—— 2-(3-hydroxy-4,4-dimethyl-1-oxido-5-phenyl-2H-imidazol-1-ium-2-yl)phenol 122981-44-6 C17H18N2O3
2-(3-hydroxy-4,4-dimethyl-1-oxido-5-phenyl-2H-imidazol-1-ium-2-yl)phenol
—— 7-methylbenzo[c][1,2]oxaborole-1,5(3H)-diol 1319804-01-7 C8H9BO3
7-methylbenzo[c][1,2]oxaborole-1,5(3H)-diol
—— (-)-(S)-5-bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxy-2-methoxybenzamide 107188-79-4 C15H21BrN2O3
(-)-(S)-5-bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxy-2-methoxybenzamide
—— 2-bromo-4,6-dichloro-3-methoxyphenol 1428470-51-2 C7H5BrCl2O2
2-bromo-4,6-dichloro-3-methoxyphenol
—— 6-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol 1319803-98-9 C7H6BFO3
6-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol
—— 2-decyl-5-(4-hydroxyphenyl) thiophene 140383-05-7 C20H28OS
2-decyl-5-(4-hydroxyphenyl) thiophene
—— 4-[3-(butyldimethylsilyl)-propoxy]phenol 142051-40-9 C15H26O2Si
4-[3-(butyldimethylsilyl)-propoxy]phenol
—— 2,5-dihydroxyphenyl 4-N-morpholinobutyl sulfide hydrochloride 123192-54-1 C14H21NO3S*ClH
2,5-dihydroxyphenyl 4-N-morpholinobutyl sulfide hydrochloride
—— 7-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol 1319804-00-6 C7H6BFO3
7-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol
—— 2,3-bis(n-butylthio)-4-hydroxy-5-methoxybenzaldehyde 157458-10-1 C16H24O3S2
2,3-bis(n-butylthio)-4-hydroxy-5-methoxybenzaldehyde
—— 2,3-dibromo-4-hydroxy-5-methoxybenzonitrile 330462-54-9 C8H5Br2NO2
2,3-dibromo-4-hydroxy-5-methoxybenzonitrile
—— 2-(5-(phenylamino)-1,3,4-oxadiazol-yl)phenol 94507-86-5 C14H11N3O2
2-(5-(phenylamino)-1,3,4-oxadiazol-yl)phenol
—— 3-isopropyl-6-methoxycatechol 883745-84-4 C10H14O3
3-isopropyl-6-methoxycatechol
—— (R)-hydroxy-(4-hydroxy-phenyl)-acetic acid methyl ester 139563-62-5 C9H10O4
(R)-hydroxy-(4-hydroxy-phenyl)-acetic acid methyl ester
—— 3-(3-hydroxyphenyl)thieno[2,3-d]isoxazole 110894-91-2 C11H7NO2S
3-(3-hydroxyphenyl)thieno[2,3-d]isoxazole
—— 2-(4-hydroxy-3-methoxybenzylidene)-1-(1H-benzimidazol-2-yl)hydrazine 60059-55-4 C15H14N4O2
2-(4-hydroxy-3-methoxybenzylidene)-1-(1H-benzimidazol-2-yl)hydrazine
—— (E)-4,5-dihydroxy-2,β-dinitrostyrene 96806-57-4 C8H6N2O6
(E)-4,5-dihydroxy-2,β-dinitrostyrene
—— (E)-4,5-dihydroxy-2,β-dinitrostyrene 98369-55-2 C8H8N2O7
(E)-4,5-dihydroxy-2,β-dinitrostyrene
—— 3-hydroxy-1-(heptadecadien-(8.11)-yl)-benzene 112115-68-1 C23H36O
3-hydroxy-1-(heptadecadien-(8.11)-yl)-benzene
—— (2S,8R,14R,20S)-2,8,14,20-tetrakis(2-methylpropyl)-5-(prop-2-enoxymethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-4,6,10,12,16,18,22,24-octol 1469921-82-1 C48H62O9
(2S,8R,14R,20S)-2,8,14,20-tetrakis(2-methylpropyl)-5-(prop-2-enoxymethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene-4,6,10,12,16,18,22,24-octol
—— 4-(2-Methyl-3-phenyl-3,4-dihydropyrazol-5-yl)phenol 1453487-89-2 C16H16N2O
4-(2-Methyl-3-phenyl-3,4-dihydropyrazol-5-yl)phenol
—— 4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenol 2515-57-3 C21H18N2O
4-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)phenol
—— 1-(2,5-difluoro-3-hydroxy-6 nitrophenyl)propan-2-one 1609119-36-9 C9H7F2NO4
1-(2,5-difluoro-3-hydroxy-6 nitrophenyl)propan-2-one