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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-[(dimethylamino)methyl]-6-methyl-4-(trifluoromethoxy)phenol 933673-43-9 C11H14F3NO2
2-[(dimethylamino)methyl]-6-methyl-4-(trifluoromethoxy)phenol
—— N-[(2-hydroxyphenyl)methylidene]acetamide 636-15-7 C9H9NO2
N-[(2-hydroxyphenyl)methylidene]acetamide
—— (E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-(4-hydroxyphenyl)butyl)acrylamide 1369406-15-4 C19H18BrN3O2
(E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-(4-hydroxyphenyl)butyl)acrylamide
—— N-[3-(4-hydroxyphenyl)propyl]thiophene-2-sulfonamide 1261033-67-3 C13H15NO3S2
N-[3-(4-hydroxyphenyl)propyl]thiophene-2-sulfonamide
—— 3-iodo-8-(2-hydroxyphenyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 1310053-42-9 C15H9IN4O2
3-iodo-8-(2-hydroxyphenyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
—— 2-(1,1-dimethylethyl)-6-(1,1-dimethyl-2-hydroxyethyl)-4-methoxyphenol 132122-36-2 C15H24O3
2-(1,1-dimethylethyl)-6-(1,1-dimethyl-2-hydroxyethyl)-4-methoxyphenol
—— Methyl 2,3-dibromo-3-(4-hydroxy-3-methoxyphenyl)propanoate 5396-66-7 C11H12Br2O4
Methyl 2,3-dibromo-3-(4-hydroxy-3-methoxyphenyl)propanoate
—— 4-amino-5-hydroxy-2-methylbenzonitrile 1134197-96-8 C8H8N2O
4-amino-5-hydroxy-2-methylbenzonitrile
—— 5-Bromo-2-hydroxy-3-nitro-N-tert-butylbenzenesulfonamide 123222-01-5 C10H13BrN2O5S
5-Bromo-2-hydroxy-3-nitro-N-tert-butylbenzenesulfonamide
—— (4R,5R)-(+)-5-ethyl-1-(4-hydroxy-3-methoxyphenethyl)-2-oxo-4-piperidineacetic acid 82260-60-4 C18H25NO5
(4R,5R)-(+)-5-ethyl-1-(4-hydroxy-3-methoxyphenethyl)-2-oxo-4-piperidineacetic acid
—— (4R,5R)-(+)-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid 73608-95-4 C18H25NO5
(4R,5R)-(+)-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid
—— (4S,5R)-(-)-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid 73608-94-3 C18H25NO5
(4S,5R)-(-)-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid
—— 1-methyl-3-(3',4',5'-trimethoxyphenyl)-5-(3''-hydroxy-4''-methoxyphenyl)-4,5-dihydro-1H-pyrazole 1224606-12-5 C20H24N2O5
1-methyl-3-(3',4',5'-trimethoxyphenyl)-5-(3''-hydroxy-4''-methoxyphenyl)-4,5-dihydro-1H-pyrazole
—— 4-(3-hydroxy-4-methoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione 1073793-01-7 C20H22N2O5S
4-(3-hydroxy-4-methoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-pyrimidine-2-thione
—— 2-(2-Hydroxyphenyl)sulfinylsulfinylphenol 5417-25-4 C12H10O4S2
2-(2-Hydroxyphenyl)sulfinylsulfinylphenol
—— N-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide 831171-98-3 C12H17NO3
N-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide
—— 1-(3-hydroxy-phenyl)-2-piperidin-1-yl-ethanol 53515-92-7 C13H19NO2
1-(3-hydroxy-phenyl)-2-piperidin-1-yl-ethanol
—— 1-(3-hydroxyphenyl)ethanone O-(2-Hydroxy-2-methylpropyl)oxime 268234-24-8 C12H17NO3
1-(3-hydroxyphenyl)ethanone O-(2-Hydroxy-2-methylpropyl)oxime
—— 4-(Oxoarsanyl)benzene-1,2-diol 5425-72-9 C6H5AsO3
4-(Oxoarsanyl)benzene-1,2-diol
—— (R)-tert-butyl-N-(5-(2-hydroxy-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxylcarbonylcarbamate 1620980-84-8 C23H33N3O9S
(R)-tert-butyl-N-(5-(2-hydroxy-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxylcarbonylcarbamate
—— marinomycin C 881020-25-3 C58H76O14
marinomycin C
—— 2,4,6-Trinitrophenol-6,7-dihydro-5h-cyclopenta[b]pyridine(1:1) 5422-87-7 C14H12N4O7
2,4,6-Trinitrophenol-6,7-dihydro-5h-cyclopenta[b]pyridine(1:1)
—— marinomycin A 881020-24-2 C58H76O14
marinomycin A
—— 2-[Bis-(2,3-dimethyl-1H-indol-6-yl)-methyl]-6-methoxy-phenol 107389-16-2 C28H28N2O2
2-[Bis-(2,3-dimethyl-1H-indol-6-yl)-methyl]-6-methoxy-phenol
—— (R)-5-amino-3-(2-fluoro-5-hydroxyphenyl)-3,6,6-trimethyl-3,6-dihydro-2H-1,4-thiazine 1,1-dioxide 1600512-07-9 C13H17FN2O3S
(R)-5-amino-3-(2-fluoro-5-hydroxyphenyl)-3,6,6-trimethyl-3,6-dihydro-2H-1,4-thiazine 1,1-dioxide
—— S-phenyl 4-hydroxy-2-methoxybenzenecarbothioate 1352812-06-6 C14H12O3S
S-phenyl 4-hydroxy-2-methoxybenzenecarbothioate
—— methyl (2-fluoro-3-hydroxyphenyl)acetate 628334-73-6 C9H9FO3
methyl (2-fluoro-3-hydroxyphenyl)acetate
—— 2,4-Dibromo-6-chloro-3-methylphenol 5415-78-1 C7H5Br2ClO
2,4-Dibromo-6-chloro-3-methylphenol
—— ethyl 2-(2-hydroxy-5-methylphenyl)acetate 41873-67-0 C11H14O3
ethyl 2-(2-hydroxy-5-methylphenyl)acetate
—— (4-Hydroxyphenyl)stibonic acid 5430-19-3 C6H7O4Sb
(4-Hydroxyphenyl)stibonic acid
—— 2-(2-Amino-thiazolo[4,3-b][1,3,4]thiadiazol-5-yl)-phenol 137609-25-7 C10H9N3OS2
2-(2-Amino-thiazolo[4,3-b][1,3,4]thiadiazol-5-yl)-phenol
—— 3-bromo-2-hydroxy-4,5-dimethoxybenzaldehyde 109765-52-8 C9H9BrO4
3-bromo-2-hydroxy-4,5-dimethoxybenzaldehyde
—— 3-bromo-1,2-dihydroxy-4,5-dimethoxybenzene 109765-53-9 C8H9BrO4
3-bromo-1,2-dihydroxy-4,5-dimethoxybenzene
—— methyl 2-(4-fluoro-2-hydroxyphenyl)propanoate 936328-98-2 C10H11FO3
methyl 2-(4-fluoro-2-hydroxyphenyl)propanoate
—— 4-Hydroxy-3-methoxy-zimtsaeure-nitril 4360-48-9 C10H9NO2
4-Hydroxy-3-methoxy-zimtsaeure-nitril
—— 2-[(Dimethylamino)methyl]-6-methoxy-4-(2,4,4-trimethylpentan-2-yl)phenol 5430-63-7 C18H31NO2
2-[(Dimethylamino)methyl]-6-methoxy-4-(2,4,4-trimethylpentan-2-yl)phenol
—— {4-[3-Methyl-5-oxo-1,5-dihydro-pyrazol-(4Z)-ylidenemethyl]-phenoxy}-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 107044-96-2 C21H20N4O5
{4-[3-Methyl-5-oxo-1,5-dihydro-pyrazol-(4Z)-ylidenemethyl]-phenoxy}-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide
—— 2,5-bis-(5'-n-hexyloxycarbonyl-2'-methyl-pent-2'-yl)-4-methoxyphenol 89829-20-9 C33H56O6
2,5-bis-(5'-n-hexyloxycarbonyl-2'-methyl-pent-2'-yl)-4-methoxyphenol
—— 2,5-bis-(5'-N,N-di-n-butylcarbamoyl-2'-methyl-pent-2'-yl)-4-methoxyphenol 89644-81-5 C37H66N2O4
2,5-bis-(5'-N,N-di-n-butylcarbamoyl-2'-methyl-pent-2'-yl)-4-methoxyphenol
—— 6-Dimethylaminomethyl-4-t-butylguaiacol 5426-16-4 C14H23NO2
6-Dimethylaminomethyl-4-t-butylguaiacol
—— 1-(2-hydroxy-4-methoxy-3-prenylphenyl)-5-phenyl-2,4-pentadien-1-one 791113-32-1 C23H24O3
1-(2-hydroxy-4-methoxy-3-prenylphenyl)-5-phenyl-2,4-pentadien-1-one
—— 2-furaldehyde[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]hydrazone 1427161-70-3 C15H13N3O3S
2-furaldehyde[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]hydrazone
—— 1,3-dihydroxy-5-<16'-(3'',5''-dihydroxyphenyl)-cis-8'-hexadecenyl>benzene 52483-23-5 C28H40O4
1,3-dihydroxy-5-<16'-(3'',5''-dihydroxyphenyl)-cis-8'-hexadecenyl>benzene
—— 2,4-bis-(4-hydroxy-3-methoxy-phenyl)-cyclobutane-1,3-dicarboxylic acid 133098-01-8 C20H20O8
2,4-bis-(4-hydroxy-3-methoxy-phenyl)-cyclobutane-1,3-dicarboxylic acid
—— 3,5-Dibromsalicylaldehyd-oxim 21386-43-6 C7H5Br2NO2
3,5-Dibromsalicylaldehyd-oxim
—— 4-(2-aminothiazol-4-yl)-3,5-dimethylphenol 1439935-96-2 C11H12N2OS
4-(2-aminothiazol-4-yl)-3,5-dimethylphenol
—— 5-[(2-Hydroxyphenyl)methylideneamino]pentane-1,2,3,4-tetrol 6936-65-8 C12H17NO5
5-[(2-Hydroxyphenyl)methylideneamino]pentane-1,2,3,4-tetrol
—— 4-allyl-2-(5-(hydroxymethyl)isoxazol-3-yl)phenol 1375102-94-5 C13H13NO3
4-allyl-2-(5-(hydroxymethyl)isoxazol-3-yl)phenol
—— 4-ethyl-2-butyl-phenol 3781-74-6 C12H18O
4-ethyl-2-butyl-phenol
—— 4-[2-(2-hydroxyethoxy)ethyl]phenol 1046818-80-7 C10H14O3
4-[2-(2-hydroxyethoxy)ethyl]phenol