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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-(2E)-2-Hexen-1-yl-4-nitrophenol 1160933-56-1 C12H15NO3
2-(2E)-2-Hexen-1-yl-4-nitrophenol
—— 2-(4-chlorophenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]acetamide 1145905-94-7 C18H17ClN2O4S
2-(4-chlorophenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]acetamide
—— 2,3-dimethoxy-6-(2-nitrovinyl)-phenol 352668-06-5 C10H11NO5
2,3-dimethoxy-6-(2-nitrovinyl)-phenol
—— 3-bromo-4-hydroxy-N-(2-hydroxyethyl)-5-nitrobenzamide 107355-70-4 C9H9BrN2O5
3-bromo-4-hydroxy-N-(2-hydroxyethyl)-5-nitrobenzamide
—— 4-[(2R,4R,5R,6R)-2,6-diethyl-5-methyl-1,3-dioxan-4-yl]-2-methoxyphenol 104789-94-8 C16H24O4
4-[(2R,4R,5R,6R)-2,6-diethyl-5-methyl-1,3-dioxan-4-yl]-2-methoxyphenol
—— 5-(2-Aminoethyl)-3-(benzenesulfonyl)benzene-1,2-diol;hydrochloride 53760-99-9 C14H16ClNO4S
5-(2-Aminoethyl)-3-(benzenesulfonyl)benzene-1,2-diol;hydrochloride
—— 2-(2'-Hydroxy-4'-bromo-5'-methoxyphenyl)methylcyclohex-1-one 166523-46-2 C14H17BrO3
2-(2'-Hydroxy-4'-bromo-5'-methoxyphenyl)methylcyclohex-1-one
—— 2,4,6-Trihydroxy-3-nitrobenzamide 136850-51-6 C7H6N2O6
2,4,6-Trihydroxy-3-nitrobenzamide
—— 5-(2-anilino-4-thiazolyl)-2,3-dihydroxybenzonitrile hydrochloride 134612-59-2 C16H11N3O2S*ClH
5-(2-anilino-4-thiazolyl)-2,3-dihydroxybenzonitrile hydrochloride
—— Rhizinonitril 38629-41-3 C10H11NO2
Rhizinonitril
—— 5-(1-Hydroxy-4,4,5,5-tetramethylimidazol-2-yl)-2-methoxyphenol 899419-47-7 C14H20N2O3
5-(1-Hydroxy-4,4,5,5-tetramethylimidazol-2-yl)-2-methoxyphenol
—— 5-(4-hydroxy-benzyl)-3-phenethyl-4,5-dihydro-isoxazole 1036384-89-0 C18H19NO2
5-(4-hydroxy-benzyl)-3-phenethyl-4,5-dihydro-isoxazole
—— 2-allyl-3-methoxy-5-methylphenol 65632-89-5 C11H14O2
2-allyl-3-methoxy-5-methylphenol
—— 1-Piperazinepropionic acid, alpha-di-2-thienylmethylene-4-methyl-, ethyl ester, dipicrate 103278-63-3 C31H30N8O16S2
1-Piperazinepropionic acid, alpha-di-2-thienylmethylene-4-methyl-, ethyl ester, dipicrate
—— 6-allyl-3-bromo-2-chlorophenol 1014625-98-9 C9H8BrClO
6-allyl-3-bromo-2-chlorophenol
—— 2-O-tert-butyl 1-O-methyl (1R,2R)-1-(3-hydroxyphenyl)cyclopropane-1,2-dicarboxylate 556105-09-0 C16H20O5
2-O-tert-butyl 1-O-methyl (1R,2R)-1-(3-hydroxyphenyl)cyclopropane-1,2-dicarboxylate
—— 3-(4-Hydroxy-3,5-dinitrophenyl)propanehydrazide 203626-59-9 C9H10N4O6
3-(4-Hydroxy-3,5-dinitrophenyl)propanehydrazide
—— 4'-Hydroxy-3'-methoxy-4-stilbazol-methoiodid 31054-25-8 C15H16NO2*I
4'-Hydroxy-3'-methoxy-4-stilbazol-methoiodid
—— 3-(3,4-dimethoxyphenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydrothieno[3,2-b]pyridin-5(4H)-one 1011407-64-9 C22H21NO5S
3-(3,4-dimethoxyphenyl)-7-(3-hydroxy-4-methoxyphenyl)-6,7-dihydrothieno[3,2-b]pyridin-5(4H)-one
—— Diphenyliodanium;2,4,6-trinitrophenol 6293-65-8 C18H13IN3O7+
Diphenyliodanium;2,4,6-trinitrophenol
—— 2-[1-hydroxy-3-(2,2,3,3,4,4,5,5,6,6,6-undecafluoro-hexyloxymethyl)but-3-enyl]phenol 1000170-39-7 C17H15F11O3
2-[1-hydroxy-3-(2,2,3,3,4,4,5,5,6,6,6-undecafluoro-hexyloxymethyl)but-3-enyl]phenol
—— 4-{(Z)-[4-Methyl-3-(prop-2-en-1-yl)-1,3-thiazol-2(3H)-ylidene]amino}phenol 777849-02-2 C13H14N2OS
4-{(Z)-[4-Methyl-3-(prop-2-en-1-yl)-1,3-thiazol-2(3H)-ylidene]amino}phenol
—— 2,5-bis(phenylselenylmethyl)benzene-1,4-diol 947326-52-5 C20H18O2Se2
2,5-bis(phenylselenylmethyl)benzene-1,4-diol
—— 3-{(E)-[4-Methyl-3-(prop-2-en-1-yl)-1,3-thiazol-2(3H)-ylidene]amino}phenol 478019-60-2 C13H14N2OS
3-{(E)-[4-Methyl-3-(prop-2-en-1-yl)-1,3-thiazol-2(3H)-ylidene]amino}phenol
—— Adamantanyl trihydroxybenzamide 343346-17-8 C17H21NO4
Adamantanyl trihydroxybenzamide
—— Sodium;hydroxy-(3-hydroxyphenyl)methanesulfonate 19473-06-4 C7H7O5S*Na
Sodium;hydroxy-(3-hydroxyphenyl)methanesulfonate
—— 3-Chlor-5-methyl-brenzcatechin 3978-66-3 C7H7ClO2
3-Chlor-5-methyl-brenzcatechin
—— 3,5-Bis(hydroxymethyl)-4-methylphenol 1403245-24-8 C9H12O3
3,5-Bis(hydroxymethyl)-4-methylphenol
—— Piperazin-bis(2,4,5-trichlorphenolat) 3689-65-4 C4H10N2*C6H3Cl3O
Piperazin-bis(2,4,5-trichlorphenolat)
—— 2,4,6-trifluoroglucinol 570391-17-2 C6H3F3O3
2,4,6-trifluoroglucinol
—— 1-(2'-hydroxy-3'-prenyl-4'-methoxyphenyl)-5-methyl-2,4-hexadien-1-one 791113-35-4 C19H24O3
1-(2'-hydroxy-3'-prenyl-4'-methoxyphenyl)-5-methyl-2,4-hexadien-1-one
—— 3-Dimethylamino-4-hydroxy-5-methoxy-benzaldehyde 396068-88-5 C10H13NO3
3-Dimethylamino-4-hydroxy-5-methoxy-benzaldehyde
—— 2-(Difluoromethyl)-6-methylphenol 499236-34-9 C8H8F2O
2-(Difluoromethyl)-6-methylphenol
—— 4-Methyl-2-(2-thienyl)phenol 944241-63-8 C11H10OS
4-Methyl-2-(2-thienyl)phenol
—— 3-(2-hydroxyphenyl)propyl-1-methyl ether 330976-51-7 C10H14O2
3-(2-hydroxyphenyl)propyl-1-methyl ether
—— 3,5-dimethyl-4-(phenylmethoxy)phenol 147351-66-4 C15H16O2
3,5-dimethyl-4-(phenylmethoxy)phenol
—— 4-Hydroxy-2-iodo-6-nitrobenzonitrile 124034-99-7 C7H3IN2O3
4-Hydroxy-2-iodo-6-nitrobenzonitrile
—— 3-(β-hydroxyethylthio)-4-nitrophenol 776-78-3 C8H9NO4S
3-(β-hydroxyethylthio)-4-nitrophenol
—— 3-Nitro-N-(2-Hydroxypropyl)-4-Aminophenol 92982-24-6 C9H12N2O4
3-Nitro-N-(2-Hydroxypropyl)-4-Aminophenol
—— 2-(1-hydroxyethyl)-3-nitrophenol 406212-36-0 C8H9NO4
2-(1-hydroxyethyl)-3-nitrophenol
—— 3,4-dichloro-5-methylcatechol 33963-44-9 C7H6Cl2O2
3,4-dichloro-5-methylcatechol
—— 2-(Oxiran-2-ylmethoxymethyl)oxirane;phenol 98460-24-3 C18H22O5
2-(Oxiran-2-ylmethoxymethyl)oxirane;phenol
—— Diisooctylphenol 85958-96-9 C22H38O
Diisooctylphenol
—— 5-(2-furyl)resorcinol 55086-85-6 C10H8O3
5-(2-furyl)resorcinol
—— 2-Cyclopent-3-enylmethyl-5-methoxy-phenol 248276-06-4 C13H16O2
2-Cyclopent-3-enylmethyl-5-methoxy-phenol
—— 2-(Benzo[1,3,2]oxathiastibol-2-ylsulfanyl)-phenol 61329-26-8 C12H9O2S2Sb
2-(Benzo[1,3,2]oxathiastibol-2-ylsulfanyl)-phenol
—— Phenol, 2,3-dibromo-4-nitro- 76362-00-0 C6H3Br2NO3
Phenol, 2,3-dibromo-4-nitro-
—— 4-[(2R,4R,5S,6R)-2,6-diethyl-5-methyl-1,3-dioxan-4-yl]-2-methoxyphenol 104789-94-8 C16H24O4
4-[(2R,4R,5S,6R)-2,6-diethyl-5-methyl-1,3-dioxan-4-yl]-2-methoxyphenol
—— 2-methoxy-4-[(2R,4R,5R,6R)-5-methyl-2,6-dipentyl-1,3-dioxan-4-yl]phenol 104789-97-1 C22H36O4
2-methoxy-4-[(2R,4R,5R,6R)-5-methyl-2,6-dipentyl-1,3-dioxan-4-yl]phenol
—— 3-methoxy-4-(methylsulfonyloxy)phenethyl methanesulfonate 218139-48-1 C11H16O7S2
3-methoxy-4-(methylsulfonyloxy)phenethyl methanesulfonate