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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
—— (+/-)-2,6-Dimethyl-4-<4-<(trimethylsilyl)methyl>-3-<(trimethylsilyl)oxy>-4-pentenyl>phenol 118630-89-0 C20H36O2Si2
(+/-)-2,6-Dimethyl-4-<4-<(trimethylsilyl)methyl>-3-<(trimethylsilyl)oxy>-4-pentenyl>phenol
—— 4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-iodo-5,6-dimethoxy-3-methylphenol 153693-56-2 C26H31IO4Si
4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-iodo-5,6-dimethoxy-3-methylphenol
—— 3-Hydroxy-4-methoxy-6-methyltoluchinol 7558-44-3 C9H12O4
3-Hydroxy-4-methoxy-6-methyltoluchinol
—— 2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethanol 365572-23-2 C12H17BrO3
2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethanol
—— 4-ethyl-2-bromo-5-methyl-phenol 854907-91-8 C9H11BrO
4-ethyl-2-bromo-5-methyl-phenol
—— 4-Chlor-2-mercapto-resorcinol 2748-45-0 C6H5ClO2S
4-Chlor-2-mercapto-resorcinol
—— 2-(N-Isopropyl-hydrazinomethyl)-phenol 94215-52-8 C10H16N2O
2-(N-Isopropyl-hydrazinomethyl)-phenol
—— 3-(1,4,5,6-tetrahydro-pyridazin-3-yl)-phenol 28858-19-7 C10H12N2O
3-(1,4,5,6-tetrahydro-pyridazin-3-yl)-phenol
—— (2-hydroxy-5-chlorobenzylideneamino)acetonitrile 1279019-02-1 C9H7ClN2O
(2-hydroxy-5-chlorobenzylideneamino)acetonitrile
—— (1R,3S,7S,10R,11S,12S,16S)-carbonic acid 10-allyl-7-hydroxy-8,8,12,16-tetramethyl-3-(2-methyl-benzothiazol-5-yl)-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-11-yl ester 4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-3-nitro-benzyl ester 658055-28-8 C46H54N4O13S
(1R,3S,7S,10R,11S,12S,16S)-carbonic acid 10-allyl-7-hydroxy-8,8,12,16-tetramethyl-3-(2-methyl-benzothiazol-5-yl)-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-11-yl ester 4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-3-nitro-benzyl ester
—— N'-[1-(3-Hydroxy-phenyl)-meth-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester 91880-53-4 C10H12N2O3
N'-[1-(3-Hydroxy-phenyl)-meth-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester
—— 4-(Methyl-hydrazonomethyl)-phenol 67175-16-0 C8H10N2O
4-(Methyl-hydrazonomethyl)-phenol
—— 5,11,17-trimethyl-23-[5-(25,26,27,28-tetrahydroxy-11,17,23-trimethyl-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)pentyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol 124028-43-9 C67H68O8
5,11,17-trimethyl-23-[5-(25,26,27,28-tetrahydroxy-11,17,23-trimethyl-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl)pentyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
—— 4-(4,6-dimethyl-pyrimidin-2-yl)-phenol 81015-35-2 C12H12N2O
4-(4,6-dimethyl-pyrimidin-2-yl)-phenol
—— 5-(3-((furan-2-yl)methyl)-4-phenyloxazolidin-2-yl)-2-methoxyphenol 1266389-69-8 C21H21NO4
5-(3-((furan-2-yl)methyl)-4-phenyloxazolidin-2-yl)-2-methoxyphenol
—— 5-Hexylmercaptomethyl-2-hydroxy-3-methoxy-benzaldehyd 2931-99-9 C15H22O3S
5-Hexylmercaptomethyl-2-hydroxy-3-methoxy-benzaldehyd
—— 1-(2-Hydroxy-4,5,6-trimethoxyphenyl)but-2-yn-1-one 128190-97-6 C13H14O5
1-(2-Hydroxy-4,5,6-trimethoxyphenyl)but-2-yn-1-one
—— 3-(2,3-dichloro-4-hydroxyphenyl)-1-(5-phenylthien-2-yl)-propan-1-one 1040563-32-3 C19H14Cl2O2S
3-(2,3-dichloro-4-hydroxyphenyl)-1-(5-phenylthien-2-yl)-propan-1-one
—— N-<2-(4-methoxyphenyl)ethoxy>acetamide 121989-64-8 C11H15NO3
N-<2-(4-methoxyphenyl)ethoxy>acetamide
—— 3-Jod-4-hydroxy-5-nitro-benzalhydroxylamin 3861-59-4 C7H5IN2O4
3-Jod-4-hydroxy-5-nitro-benzalhydroxylamin
—— Salicyliden-bis-carbamidsaeure-ethylester 96485-94-8 C13H18N2O5
Salicyliden-bis-carbamidsaeure-ethylester
—— 2,5-dibutyl-4-[2-(dimethylphenylsilyl)ethyl]phenol 1230388-47-2 C24H36OSi
2,5-dibutyl-4-[2-(dimethylphenylsilyl)ethyl]phenol
—— 3,6-bis-(2-hydroxybenzyl)piperazine-2,5-dione 872272-56-5 C18H18N2O4
3,6-bis-(2-hydroxybenzyl)piperazine-2,5-dione
—— 2-(4-Hydroxyphenyl)-4,r-5-dimethyl-t-6-phenyl-5,6-dihydro-4H-1,3,4-thiadiazin 17144-07-9 C17H18N2OS
2-(4-Hydroxyphenyl)-4,r-5-dimethyl-t-6-phenyl-5,6-dihydro-4H-1,3,4-thiadiazin
—— 6-(o-Hydroxy-benzyliden)-3-isopropyliden-2,5-piperazindion 10414-80-9 C14H14N2O3
6-(o-Hydroxy-benzyliden)-3-isopropyliden-2,5-piperazindion
—— 4-Hydroxy-3-methyl-benzol-<1-azo-3>pyrazol 14521-82-5 C10H10N4O
4-Hydroxy-3-methyl-benzol-<1-azo-3>pyrazol
—— (Z)-6-methyl-2-[(3-methyl )-3-pentenyl]phenol 1383253-09-5 C13H18O
(Z)-6-methyl-2-[(3-methyl )-3-pentenyl]phenol
—— 473896-15-0 C22H30O2S4
—— 1-(1-Adamantyl)-3-[(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]thiourea 32403-43-3 C20H27N3O3S
1-(1-Adamantyl)-3-[(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]thiourea
—— <3-Hydroxy-4-methyl-phenyl>-phosphonsaeure 102170-18-3 C7H9O4P
<3-Hydroxy-4-methyl-phenyl>-phosphonsaeure
—— 2-m-Hydroxyphenylpent-4-en-2-ol 32578-07-7 C11H14O2
2-m-Hydroxyphenylpent-4-en-2-ol
—— N-(3-hydroxy-4-methoxyphenethyl)-3-(2-iodo-5-methoxyphenyl)propionamide 250687-92-4 C19H22INO4
N-(3-hydroxy-4-methoxyphenethyl)-3-(2-iodo-5-methoxyphenyl)propionamide
—— 3-(4-hydroxy-2-methylphenylethynyl)-2-methylcyclohex-2-enone 1134798-87-0 C16H16O2
3-(4-hydroxy-2-methylphenylethynyl)-2-methylcyclohex-2-enone
—— (3-fluorophenyl)-[3-(2-hydroxy-3-methoxyphenyl)-4,5-dihydropyrazol-1-yl]methanone 1417708-69-0 C17H15FN2O3
(3-fluorophenyl)-[3-(2-hydroxy-3-methoxyphenyl)-4,5-dihydropyrazol-1-yl]methanone
—— Atranol 4-propyl-thiosemicarbazon 21236-32-8 C12H17N3O2S
Atranol 4-propyl-thiosemicarbazon
—— 2-methoxy-4-(5H-thiazolo[3,2-a]quinazolin-1-yl)-phenol 15371-19-4 C17H14N2O2S
2-methoxy-4-(5H-thiazolo[3,2-a]quinazolin-1-yl)-phenol
—— 4,6,10,12,16,18,22,24-octamethylpentacyclo<19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>15,19</sup>>octacosa-1(25),3,5,,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol 123775-99-5 C36H40O4
4,6,10,12,16,18,22,24-octamethylpentacyclo<19.3.1.1<sup>3,7</sup>.1<sup>9,13</sup>.1<sup>15,19</sup>>octacosa-1(25),3,5,,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol
—— antimony(III) quinoxydichloride 92919-97-6 C6H5Cl2O2Sb
antimony(III) quinoxydichloride
—— 4-(2,4-Dihydroxy-phenyl)-octan 6565-73-7 C14H22O2
4-(2,4-Dihydroxy-phenyl)-octan
—— 4-(adamantan-2-ylaminomethyl)benzene-1,2-diol 1152823-23-8 C17H23NO2
4-(adamantan-2-ylaminomethyl)benzene-1,2-diol
—— 4,6-Diaethyl-pyrogallol 99173-18-9 C10H14O3
4,6-Diaethyl-pyrogallol
—— thiocyanato-acetic acid salicylidenehydrazide 110177-87-2 C10H9N3O2S
thiocyanato-acetic acid salicylidenehydrazide
—— p-Hydroxybenzoldiazocyanid 32487-25-5 C7H5N3O
p-Hydroxybenzoldiazocyanid
—— 4-methyl-2-(4-methylpiperazin-1-ylmethyleneamino)phenol 1323158-74-2 C13H18N2O
4-methyl-2-(4-methylpiperazin-1-ylmethyleneamino)phenol
—— 2-Bromo-6-[[2-[(3-bromo-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol 1354637-49-2 C20H14Br2N2O2
2-Bromo-6-[[2-[(3-bromo-2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol
—— (1RS,2RS,3SR)-1-(3,5-dihydroxy-4-methoxyphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutyl acetate 138566-68-4 C23H30O8
(1RS,2RS,3SR)-1-(3,5-dihydroxy-4-methoxyphenyl)-4-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutyl acetate
—— 2-[(4-Chloro-phenyl)-hydrazono]-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-4-one 18101-26-3 C17H14ClN3O3S
2-[(4-Chloro-phenyl)-hydrazono]-5-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-4-one
—— N-(1,1-Dimethyl-2-benzoxyethyl)-N'-(2-hydroxy-4-nitrophenyl)urea 201043-81-4 C18H21N3O5
N-(1,1-Dimethyl-2-benzoxyethyl)-N'-(2-hydroxy-4-nitrophenyl)urea
—— 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(2-methylsulfonylethyl)phenol 108930-08-1 C15H25NO4S
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(2-methylsulfonylethyl)phenol
—— 3-(2-thienyl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol 268559-89-3 C14H10N2OS
3-(2-thienyl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol