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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
—— 2,4-dibromo-6-(3-furan-2-yl-isoxazol-5-yl)-phenol 60477-84-1 C13H7Br2NO3
2,4-dibromo-6-(3-furan-2-yl-isoxazol-5-yl)-phenol
—— (E)-3-(4-Hydroxy-3-methoxy-phenyl)-2-(1-methyl-1H-imidazo[4,5-b]pyridin-2-yl)-acrylonitrile 133466-09-8 C17H14N4O2
(E)-3-(4-Hydroxy-3-methoxy-phenyl)-2-(1-methyl-1H-imidazo[4,5-b]pyridin-2-yl)-acrylonitrile
—— (1'R,2'R,2''E,4E)-6-(5-t-butyldimethylsiloxy-2-hydroxy-3-methylphenyl)-1-<1',2'-dimethyl-2'-(4''-hydroxy-4''-methyl-2''-pentenoyl)cyclopentyl>-4-methyl-4-hexen-2-one 130852-46-9 C33H52O5Si
(1'R,2'R,2''E,4E)-6-(5-t-butyldimethylsiloxy-2-hydroxy-3-methylphenyl)-1-<1',2'-dimethyl-2'-(4''-hydroxy-4''-methyl-2''-pentenoyl)cyclopentyl>-4-methyl-4-hexen-2-one
—— 2-Exo-<m-hydroxybenzyl>-3-exo-hydroxy-6-endo-(cis-1-heptenyl)-bicyclo<3.1.0>hexan 59751-56-3 C20H28O2
2-Exo-<m-hydroxybenzyl>-3-exo-hydroxy-6-endo-(cis-1-heptenyl)-bicyclo<3.1.0>hexan
—— 4-Chloro-2-dimethylphosphorylphenol 512191-01-4 C8H10ClO2P
4-Chloro-2-dimethylphosphorylphenol
—— 1565828-82-1 C16H23NO5
—— 2-(2-chloro-pyridin-3-ylmethyleneamino)-phenol 69800-99-3 C12H9ClN2O
2-(2-chloro-pyridin-3-ylmethyleneamino)-phenol
—— γ-(3,4-dihydroxyphenyl)butyramide 125789-91-5 C10H13NO3
γ-(3,4-dihydroxyphenyl)butyramide
—— 3.5-Dimethyl-2-(hydroxy-4-chloropyridylmethyl)benzene-1,4-diol 162653-21-6 C14H14ClNO3
3.5-Dimethyl-2-(hydroxy-4-chloropyridylmethyl)benzene-1,4-diol
—— 2-(Tetradecylimino-methyl)-phenol 16308-57-9 C21H35NO
2-(Tetradecylimino-methyl)-phenol
—— 4-Hydroxy-3-nitrobenzaldehyde(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazone 443762-40-1 C14H11N5O3S
4-Hydroxy-3-nitrobenzaldehyde(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazone
—— 5-hexyl-2-(4-hydroxyphenyl)pyrimidine 58415-61-5 C16H20N2O
5-hexyl-2-(4-hydroxyphenyl)pyrimidine
—— (5Z)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 1181081-35-5 C15H15N3O4S
(5Z)-5-[(2-hydroxy-5-nitrophenyl)methylidene]-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-4-one
—— 5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1,2-diol;hydrobromide 97352-13-1 BrH*C12H17NO2
5-(aminomethyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1,2-diol;hydrobromide
—— 4-(4-Bromo-3-hydroxyphenyl)butanoic acid 1454928-41-6 C10H11BrO3
4-(4-Bromo-3-hydroxyphenyl)butanoic acid
—— 2-(1,3-dioxan-2-yl)-5-methoxyphenol 945656-64-4 C11H14O4
2-(1,3-dioxan-2-yl)-5-methoxyphenol
—— (4-Methoxy-phenyl)-(2,4-dihydroxy-phenyl)-tellurdibromid 108924-84-1 C13H12Br2O3Te
(4-Methoxy-phenyl)-(2,4-dihydroxy-phenyl)-tellurdibromid
—— 2,6-Dibromo-phenol; compound with tert-butylamine 100782-00-1 C4H11N*C6H4Br2O
2,6-Dibromo-phenol; compound with tert-butylamine
—— 2,2'-[(5,6,5',6'-tetrahydro-1<i>H</i>,1'<i>H</i>-3,3'-butane-1,4-diyl-bis-[1,2,4]triazin-4-ylimino)-dimethyl]-bis-phenol 63545-84-6 C24H30N8O2
2,2'-[(5,6,5',6'-tetrahydro-1<i>H</i>,1'<i>H</i>-3,3'-butane-1,4-diyl-bis-[1,2,4]triazin-4-ylimino)-dimethyl]-bis-phenol
—— 4-nitro-2-((2-(2-(pyridin-2-yl)ethylthio)ethylimino)methyl)phenol 615257-10-8 C16H17N3O3S
4-nitro-2-((2-(2-(pyridin-2-yl)ethylthio)ethylimino)methyl)phenol
—— 3-hydroxy-1-(2-hydroxy-4-methoxy-phenyl)-3-pyridin-3-yl-propan-1-one oxime 35590-57-9 C15H16N2O4
3-hydroxy-1-(2-hydroxy-4-methoxy-phenyl)-3-pyridin-3-yl-propan-1-one oxime
—— (4,5-dihydroxy-2-methoxy-phenyl)-glyoxylic acid 99548-42-2 C9H8O6
(4,5-dihydroxy-2-methoxy-phenyl)-glyoxylic acid
—— 1173198-77-0 C18H24N2OS2
—— 2-(3-anilinobutyl)-5-methylbenzene-1,4-diol 121746-64-3 C17H21NO2
2-(3-anilinobutyl)-5-methylbenzene-1,4-diol
—— 3-benzyl-2-(2-hydroxy-phenylimino)-1,1-dioxo-1λ<sup>6</sup>-thiazolidin-4-one 69583-32-0 C16H14N2O4S
3-benzyl-2-(2-hydroxy-phenylimino)-1,1-dioxo-1λ<sup>6</sup>-thiazolidin-4-one
—— 4-[(4-chloro-phenylimino)-methyl]-pyrogallol 100398-46-7 C13H10ClNO3
4-[(4-chloro-phenylimino)-methyl]-pyrogallol
—— (2S,4R,6S)-2-(3'',4''-methylenedioxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate 1440432-06-3 C32H35BrO9
(2S,4R,6S)-2-(3'',4''-methylenedioxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate
—— 2,2-Dioxo-2,3-dihydro-1H-2λ<sup>6</sup>-benzo[c]thiophen-5-ol 142608-09-1 C8H8O3S
2,2-Dioxo-2,3-dihydro-1H-2λ<sup>6</sup>-benzo[c]thiophen-5-ol
—— 2,5-Dichlorhydrochinon-3,6-d2 63715-59-3 C6H4Cl2O2
2,5-Dichlorhydrochinon-3,6-d2
—— N-(2-hydroxy-5-nirobenzyl)iminodiethanol 177080-39-6 C10H14N2O5
N-(2-hydroxy-5-nirobenzyl)iminodiethanol
—— 4-butyl-1-(4-hydroxy-phenyl)-4-morpholin-4-ylmethyl-2-phenyl-pyrazolidine-3,5-dione 31118-97-5 C24H29N3O4
4-butyl-1-(4-hydroxy-phenyl)-4-morpholin-4-ylmethyl-2-phenyl-pyrazolidine-3,5-dione
—— Sulfamic acid 2-(4-hydroxyphenoxy)ethyl ester 137208-81-2 C8H11NO5S
Sulfamic acid 2-(4-hydroxyphenoxy)ethyl ester
—— 2-chloro-5-amino-6-nitro phenol hydrochloride 62106-34-7 C6H5ClN2O3*ClH
2-chloro-5-amino-6-nitro phenol hydrochloride
—— 5-(3-amino-2-hydroxypropyl)amino-7-(2-hydroxy-3-methoxybenzyl)amino-3-isopropylpyrazolo[4,3-d]pyrimidine 1257627-69-2 C19H27N7O3
5-(3-amino-2-hydroxypropyl)amino-7-(2-hydroxy-3-methoxybenzyl)amino-3-isopropylpyrazolo[4,3-d]pyrimidine
—— 1-<4-Hydroxy-phenaethyl-4.4.6-trimethyl-3.4-dihydro-1H-pyrimidin-2-thion 58125-67-0 C15H20N2OS
1-<4-Hydroxy-phenaethyl-4.4.6-trimethyl-3.4-dihydro-1H-pyrimidin-2-thion
—— (3-Bromo-4-hydroxy-5-methoxy-phenyl)-m-tolylamino-acetonitrile 73022-16-9 C16H15BrN2O2
(3-Bromo-4-hydroxy-5-methoxy-phenyl)-m-tolylamino-acetonitrile
—— 2-methyl-4-(β-hydroxyethylamino)-5-nitro-phenol 65235-25-8 C9H12N2O4
2-methyl-4-(β-hydroxyethylamino)-5-nitro-phenol
—— 3-[5-(2-bromo-5-hydroxy-phenyl)-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-3-yl]-4-hydroxy-6-methyl-pyran-2-one 56364-41-1 C21H17BrN2O4
3-[5-(2-bromo-5-hydroxy-phenyl)-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazol-3-yl]-4-hydroxy-6-methyl-pyran-2-one
—— 1277180-66-1 C28H50O3
—— 2-Heptadecyl-5-methoxy-3-methyl-phenol 855346-26-8 C25H44O2
2-Heptadecyl-5-methoxy-3-methyl-phenol
—— 66100-52-5 C8H8O4
—— 84118-81-0 C18H19BrS
—— 4-chloro-2-(3-furan-2-yl-isoxazol-5-yl)-5-methyl-phenol 60477-83-0 C14H10ClNO3
4-chloro-2-(3-furan-2-yl-isoxazol-5-yl)-5-methyl-phenol
—— N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]hexadecanamide 74064-89-4 C24H41NO4
N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]hexadecanamide
—— 1297551-76-8 C3H6N2O*C3H9N*C6H3N3O7*C75H96O12*C99H129N9O9
—— Acetic acid 2-(4-bromo-2,5-bis-cyanomethyl-phenoxy)-ethyl ester 58268-42-1 C14H13BrN2O3
Acetic acid 2-(4-bromo-2,5-bis-cyanomethyl-phenoxy)-ethyl ester
—— 4-[4-(4-hydroxy-phenethyl)-phenyl]-5<i>H</i>-furan-2-one 58789-87-0 C18H16O3
4-[4-(4-hydroxy-phenethyl)-phenyl]-5<i>H</i>-furan-2-one
—— benzylidene-(4-hydroxy-benzylidene)-hydrazine 55621-05-1 C14H12N2O
benzylidene-(4-hydroxy-benzylidene)-hydrazine
—— N-(2'-Hydroxy-biphenyl-2-yl)-N'-methyl-2-nitrilo-acetamidine 69605-57-8 C15H13N3O
N-(2'-Hydroxy-biphenyl-2-yl)-N'-methyl-2-nitrilo-acetamidine
—— 6-(N,N-dimethylamino)methyl-2,3,4-trimethoxyphenol 39068-86-5 C12H19NO4
6-(N,N-dimethylamino)methyl-2,3,4-trimethoxyphenol