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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
—— N-(5-chlorosalicylidene)-3-[bis(5-methyl-2-furyl)methyl]aniline 1000414-92-5 C24H20ClNO3
N-(5-chlorosalicylidene)-3-[bis(5-methyl-2-furyl)methyl]aniline
—— carbonic acid 2-bromo-4-heptyl-3-hydroxy-phenyl ester tert-butyl ester 680997-61-9 C18H27BrO4
carbonic acid 2-bromo-4-heptyl-3-hydroxy-phenyl ester tert-butyl ester
—— 7-Brom-3-ethyl-5-phenyl-2<2(3-ethyl-4-oxo-2-thioxo-oxazolidin-5-yliden)ethyliden>benzoxazol 17121-48-1 C22H19BrN2O3S
7-Brom-3-ethyl-5-phenyl-2<2(3-ethyl-4-oxo-2-thioxo-oxazolidin-5-yliden)ethyliden>benzoxazol
—— (6Z)-6-(anilinomethylidene)cyclohexa-2,4-dien-1-one;nickel(2+) 14266-60-5 C26H22N2NiO2+2
(6Z)-6-(anilinomethylidene)cyclohexa-2,4-dien-1-one;nickel(2+)
—— 3,5-bis(ethylsulfanylmethyl)phenol 194864-28-3 C12H18OS2
3,5-bis(ethylsulfanylmethyl)phenol
—— (η6-phenol)tricarbonylchromium(0) 32802-03-2 C9H6CrO4
(η6-phenol)tricarbonylchromium(0)
—— N-(Trifluoroacetyl)-3-hydroxy-4-iodophenylethylamine 171515-39-2 C10H9F3INO2
N-(Trifluoroacetyl)-3-hydroxy-4-iodophenylethylamine
—— 4-(4,6-Bis-ethylamino-[1,3,5]triazin-2-ylamino)-benzoic acid [1-(2-hydroxy-4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 119868-62-1 C22H26N8O3
4-(4,6-Bis-ethylamino-[1,3,5]triazin-2-ylamino)-benzoic acid [1-(2-hydroxy-4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide
—— 2-(3,5-Dibromo-2-hydroxy-phenyl)-1-(4,5-dibromo-1H-pyrrol-2-yl)-ethanone 925213-22-5 C12H7Br4NO2
2-(3,5-Dibromo-2-hydroxy-phenyl)-1-(4,5-dibromo-1H-pyrrol-2-yl)-ethanone
—— 2-tert-Butoxy-3-chloro-phenol 56207-42-2 C10H13ClO2
2-tert-Butoxy-3-chloro-phenol
—— 2-Bromo-4-[(propylamino)methylidene]cyclohexa-2,5-dien-1-one 61131-61-1 C10H12BrNO
2-Bromo-4-[(propylamino)methylidene]cyclohexa-2,5-dien-1-one
—— 2-hydroxy-5-nitro-3-sulfobenzenediazonium;chloride 721442-67-7 C6H4N3O6S*Cl
2-hydroxy-5-nitro-3-sulfobenzenediazonium;chloride
—— 2-((2-(2-(2-hydroxybenzylideneamino)ethylthio)ethylimino)methyl)phenol 54305-74-7 C18H20N2O2S
2-((2-(2-(2-hydroxybenzylideneamino)ethylthio)ethylimino)methyl)phenol
—— 3-Acetyl-dihydrohispidin 92550-61-3 C15H14O6
3-Acetyl-dihydrohispidin
—— N-benzyl-N-methyldopamine hydrochloride 106149-79-5 C16H19NO2*ClH
N-benzyl-N-methyldopamine hydrochloride
—— 2,5-Dimethyl-2,5-diethyl-4-(2-hydroxy-benzyliden)-tetrahydrofuranon-3 94958-70-0 C17H22O3
2,5-Dimethyl-2,5-diethyl-4-(2-hydroxy-benzyliden)-tetrahydrofuranon-3
—— 3,5-Bis(tert-butylsulfanylmethyl)phenol 194864-27-2 C16H26OS2
3,5-Bis(tert-butylsulfanylmethyl)phenol
—— p-t-Amylphenol 98448-58-9 C11H16O2
p-t-Amylphenol
—— 3-[2,2-bis[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propyl]phenol 367272-32-0 C27H26N2O3
3-[2,2-bis[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propyl]phenol
—— 2-{3-[Bis-(2-methoxy-ethyl)-amino]-isoxazol-5-yl}-5-methoxy-phenol 247148-00-1 C16H22N2O5
2-{3-[Bis-(2-methoxy-ethyl)-amino]-isoxazol-5-yl}-5-methoxy-phenol
—— 5-cyano-4-(4-hydroxy-3-methoxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 846546-78-9 C18H20N2O4
5-cyano-4-(4-hydroxy-3-methoxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester
—— 3,5-Dimethyl-α,α-bis-(difluor-monochlormethyl)-4-hydroxy-benzylchlorid 16878-09-4 C11H9Cl3F4O
3,5-Dimethyl-α,α-bis-(difluor-monochlormethyl)-4-hydroxy-benzylchlorid
—— [3-[(3,5-Dibromo-2-hydroxyphenyl)methylideneamino]phenyl]boronic acid 1174064-40-4 C13H10BBr2NO3
[3-[(3,5-Dibromo-2-hydroxyphenyl)methylideneamino]phenyl]boronic acid
—— N-n-Butyl-2-hydroxy-5-nitro-α-toluenesulfonamide 76927-72-5 C11H16N2O5S
N-n-Butyl-2-hydroxy-5-nitro-α-toluenesulfonamide
—— 2-((2-(pyridin-2-yl)hydrazono)methyl)-5-methoxyphenol 1391089-85-2 C13H13N3O2
2-((2-(pyridin-2-yl)hydrazono)methyl)-5-methoxyphenol
—— [p-tert-butylcalix[4]arene(-3H)]W(PMe3)3H3 920749-50-4 C53H83O4P3W
[p-tert-butylcalix[4]arene(-3H)]W(PMe3)3H3
—— 1-Phenyl-3-<2-hydroxy-3.5.6-trimethoxy-phenyl>-5-<3.4-methylendioxy-phenyl>-pyrazolin 95868-14-7 C25H24N2O6
1-Phenyl-3-<2-hydroxy-3.5.6-trimethoxy-phenyl>-5-<3.4-methylendioxy-phenyl>-pyrazolin
—— 3-{[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-5-morpholin-4-ylmethyl-oxazolidin-2-one 92650-24-3 C15H19N3O4
3-{[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-5-morpholin-4-ylmethyl-oxazolidin-2-one
—— 3-<3-Hydroxy-4,6-diiodphenyl>-propionsaeure-methylester 90917-56-9 C10H10I2O3
3-<3-Hydroxy-4,6-diiodphenyl>-propionsaeure-methylester
—— N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>chloroacetamide 53527-13-2 C11H14ClNO3
N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>chloroacetamide
—— 4-[Bis(2-hydroxyethylsulfanyl)methyl]phenol 1462982-19-9 C11H16O3S2
4-[Bis(2-hydroxyethylsulfanyl)methyl]phenol
—— (1S,8S,9S)-(12,13-Dioxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-yl)-acetic acid ethyl ester 171001-92-6 C15H18O4
(1S,8S,9S)-(12,13-Dioxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-yl)-acetic acid ethyl ester
—— 5-(4-hydroxyphenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-2,6-dicarboxylic acid diethyl ester 1403606-06-3 C20H22N2O5S
5-(4-hydroxyphenyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-2,6-dicarboxylic acid diethyl ester
—— 144305-95-3 C18H22Cl2MnN6O4
—— 2.5-Dihydroxy-4-methoxy-1-(N-benzyloxycarbonyl)-aminoaethyl-benzol 39816-43-8 C17H19NO5
2.5-Dihydroxy-4-methoxy-1-(N-benzyloxycarbonyl)-aminoaethyl-benzol
—— 2,2-Dimethyl-propionic acid 3-hydroxy-2-(2-hydroxy-phenyl)-propyl ester 881672-54-4 C14H20O4
2,2-Dimethyl-propionic acid 3-hydroxy-2-(2-hydroxy-phenyl)-propyl ester
—— 4,6-bis-(4-hydroxy-phenyl)-nonane 6052-81-9 C21H28O2
4,6-bis-(4-hydroxy-phenyl)-nonane
—— (2E,4E)-5-(2-Hydroxy-6-methyl-phenyl)-3-methyl-penta-2,4-dienoic acid 41436-00-4 C13H14O3
(2E,4E)-5-(2-Hydroxy-6-methyl-phenyl)-3-methyl-penta-2,4-dienoic acid
—— DL-3-Acetyl-5-(4-hydroxy-benzyl)-4-hydroxy-Δ<sup>3</sup>-pyrrolin-2-on 34300-67-9 C13H13NO4
DL-3-Acetyl-5-(4-hydroxy-benzyl)-4-hydroxy-Δ<sup>3</sup>-pyrrolin-2-on
—— (((4-(3,4-dihydroxyphenyl)thiazol-2-yl)amino)methylene)bis(phosphonic acid) 1353687-47-4 C10H12N2O8P2S
(((4-(3,4-dihydroxyphenyl)thiazol-2-yl)amino)methylene)bis(phosphonic acid)
—— α-(o-Hydroxy-anilino)-α-oximino-aceton 18237-84-8 C9H10N2O3
α-(o-Hydroxy-anilino)-α-oximino-aceton
—— naphthalene-2,7-diol;7,13,23,30-tetrazapentacyclo[29.2.2.23,6.214,17.219,22]hentetraconta-1(33),3(41),4,6(40),14(39),15,17(38),19,21,31,34,36-dodecaene 81667-98-3 C10H8O2*C37H46N4
naphthalene-2,7-diol;7,13,23,30-tetrazapentacyclo[29.2.2.23,6.214,17.219,22]hentetraconta-1(33),3(41),4,6(40),14(39),15,17(38),19,21,31,34,36-dodecaene
—— 5-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)benzene-1,2,3-triol 1145789-42-9 C14H9N3O6
5-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)benzene-1,2,3-triol
—— 4-Chloro-2-[2-(3,4-dimethoxyphenyl)ethoxy]pyrimidine 1185999-60-3 C14H15ClN2O3
4-Chloro-2-[2-(3,4-dimethoxyphenyl)ethoxy]pyrimidine
—— N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)isonicotinamide 1334920-04-5 C16H13N3O3S
N-(4-(4-hydroxy-3-methoxyphenyl)thiazol-2-yl)isonicotinamide
—— (E)-N'-(3,5-dibromo-4-hydroxybenzylidene)octanehydrazide 1068708-24-6 C15H20Br2N2O2
(E)-N'-(3,5-dibromo-4-hydroxybenzylidene)octanehydrazide
—— 6-Chlor-2-brom-vanillin, 6-Chlor-2-brom-4-hydroxy-3-methoxy-benzaldehyd 79005-46-2 C8H6BrClO3
6-Chlor-2-brom-vanillin, 6-Chlor-2-brom-4-hydroxy-3-methoxy-benzaldehyd
—— 4-[4-[(3-Hydroxy-1-phenylpropyl)amino]-5-methylpyrimidin-2-yl]-2-methoxyphenol 854074-16-1 C21H23N3O3
4-[4-[(3-Hydroxy-1-phenylpropyl)amino]-5-methylpyrimidin-2-yl]-2-methoxyphenol
—— cobalt(2+);(6Z)-6-[(cyclohexylamino)methylidene]cyclohexa-2,4-dien-1-one 16972-55-7 C26H34CoN2O2+2
cobalt(2+);(6Z)-6-[(cyclohexylamino)methylidene]cyclohexa-2,4-dien-1-one
—— N-[1-(4-hydroxy-3-methoxyphenyl)ethyl]octadec-9-enamide 1391847-95-2 C27H45NO3
N-[1-(4-hydroxy-3-methoxyphenyl)ethyl]octadec-9-enamide