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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
—— 4-[(R)-((2S,5R)-5-Benzyl-pyrrolidin-2-yl)-hydroxy-methyl]-phenol 92012-33-4 C18H21NO2
4-[(R)-((2S,5R)-5-Benzyl-pyrrolidin-2-yl)-hydroxy-methyl]-phenol
—— optically inactive 3.7-dihydroxy-3a.6-dimethyl-2.3.3a.4.5.9b-hexahydro-1<i>H</i>-cyclopenta[<i>a</i>]naphthalene 109496-34-6 C15H20O2
optically inactive 3.7-dihydroxy-3a.6-dimethyl-2.3.3a.4.5.9b-hexahydro-1<i>H</i>-cyclopenta[<i>a</i>]naphthalene
—— N-(2-(2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethoxy)ethyl)-3,4,5-trihydroxybenzamide 1411773-04-0 C33H46N2O6
N-(2-(2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethoxy)ethyl)-3,4,5-trihydroxybenzamide
—— 4,6-Bis-(3,5-dihydroxy-phenyl)-6-hydroxy-4-methyl-tetrahydro-pyran-2-one 51863-78-6 C18H18O7
4,6-Bis-(3,5-dihydroxy-phenyl)-6-hydroxy-4-methyl-tetrahydro-pyran-2-one
—— 4.6-dinitro-3-oxy-phenylhydrazine 861338-19-4 C6H6N4O5
4.6-dinitro-3-oxy-phenylhydrazine
—— 5-(2-hydroxy-5-nitro-anilino)-2-phenyl-1,2-dihydro-pyrazol-3-one 7186-73-4 C15H12N4O4
5-(2-hydroxy-5-nitro-anilino)-2-phenyl-1,2-dihydro-pyrazol-3-one
—— 3-bromo-4-(2,4-diamino-pyrimidin-5-ylmethyl)-2-methoxy-phenol 4871-66-3 C12H13BrN4O2
3-bromo-4-(2,4-diamino-pyrimidin-5-ylmethyl)-2-methoxy-phenol
—— 3,3-bis-(4-hydroxy-3,5-dimethoxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ<sup>6</sup>-benzo[<i>d</i>]isothiazole-2-carboxylic acid 2-cyano-ethyl ester 70367-95-2 C27H26N2O10S
3,3-bis-(4-hydroxy-3,5-dimethoxy-phenyl)-1,1-dioxo-1,3-dihydro-1λ<sup>6</sup>-benzo[<i>d</i>]isothiazole-2-carboxylic acid 2-cyano-ethyl ester
—— N-(3-Chloro-2-hydroxy-5-nitro-phenyl)-2-cyano-acetamide 50740-01-7 C9H6ClN3O4
N-(3-Chloro-2-hydroxy-5-nitro-phenyl)-2-cyano-acetamide
—— 10-(p-Hydroxyphenyl)decansaeure-essigsaeureanhydrid 53306-50-6 C18H26O4
10-(p-Hydroxyphenyl)decansaeure-essigsaeureanhydrid
—— 98861-69-9 C18H16N4O2S2
—— 1-(2-hydroxy-3,4-dimethoxy-phenyl)-3-(1-methyl-indol-3-yl)-propenone 33268-81-4 C20H19NO4
1-(2-hydroxy-3,4-dimethoxy-phenyl)-3-(1-methyl-indol-3-yl)-propenone
—— 2,4,5-Tris-(5-methyl-furan-2-yl)-4,5-dihydro-1H-imidazole; compound with picric acid 51625-64-0 C6H3N3O7*C18H18N2O3
2,4,5-Tris-(5-methyl-furan-2-yl)-4,5-dihydro-1H-imidazole; compound with picric acid
—— 1-(dichloro(3,4-dihydroxyphenyl)-l<sup>4</sup>-tellanyl)pentane-2,4-dione 122183-01-1 C11H12Cl2O4Te
1-(dichloro(3,4-dihydroxyphenyl)-l<sup>4</sup>-tellanyl)pentane-2,4-dione
—— α,α-Di-(n-butyl)-4-hydroxyphenylacetonitril 16254-47-0 C16H23NO
α,α-Di-(n-butyl)-4-hydroxyphenylacetonitril
—— N-Methylmorpholine pentachlorophenolate 126208-46-6 C5H11NO*C6HCl5O
N-Methylmorpholine pentachlorophenolate
—— 4-[4-allyloxy-6-(4-chloro-phenyl)-[1,3,5]triazin-2-yl]-benzene-1,3-diol 4686-85-5 C18H14ClN3O3
4-[4-allyloxy-6-(4-chloro-phenyl)-[1,3,5]triazin-2-yl]-benzene-1,3-diol
—— 2-[(1S)-1-Amino-2-propen-1-yl]-6-bromo-4-nitrophenol 1213113-96-2 C9H9BrN2O3
2-[(1S)-1-Amino-2-propen-1-yl]-6-bromo-4-nitrophenol
—— 5,11,17,23-tetra-tert-butyl-25,26-dihydroxycalix[4]arenetitanium(IV) dichloride 146860-36-8 C44H56O2
5,11,17,23-tetra-tert-butyl-25,26-dihydroxycalix[4]arenetitanium(IV) dichloride
—— 52244-60-7 C14H18O2
—— 4-Hydroxy-2,2',3,4',6,6'-hexamethyl-azobenzol 50393-63-0 C18H22N2O
4-Hydroxy-2,2',3,4',6,6'-hexamethyl-azobenzol
—— 2-(7-pyridin-4-yl-2,3,6,7-tetrahydro-1<i>H</i>-[1,4]diazepin-5-yl)-phenol 56686-25-0 C16H17N3O
2-(7-pyridin-4-yl-2,3,6,7-tetrahydro-1<i>H</i>-[1,4]diazepin-5-yl)-phenol
—— 55323-41-6 C19H25NO4
—— o-Bromanilin-Methylpicrinsaeure-Komplex 51010-21-0 C6H6BrN*C7H5N3O7
o-Bromanilin-Methylpicrinsaeure-Komplex
—— 4-OHC6H4Sb(SCH2CO2H)2 856066-60-9 C10H11O5S2Sb
4-OHC6H4Sb(SCH2CO2H)2
—— 2-[[2-[bis(2-hydroxyethyl)amino]ethylamino]methyl]-4-methoxyphenol 188289-00-1 C14H24N2O4
2-[[2-[bis(2-hydroxyethyl)amino]ethylamino]methyl]-4-methoxyphenol
—— 2-(Cyclohepten-1-yl)-5-methoxyphenol 1373965-40-2 C14H18O2
2-(Cyclohepten-1-yl)-5-methoxyphenol
—— 3-(4-ethoxy-phenyl)-5-(4-hydroxy-3-methoxy-benzylidene)-2-thioxo-tetrahydro-pyrimidin-4-one 53377-44-9 C20H20N2O4S
3-(4-ethoxy-phenyl)-5-(4-hydroxy-3-methoxy-benzylidene)-2-thioxo-tetrahydro-pyrimidin-4-one
—— 2-[4-(4-chloro-phenyl)-6-methoxy-[1,3,5]triazin-2-yl]-5-methoxy-phenol 4686-73-1 C17H14ClN3O3
2-[4-(4-chloro-phenyl)-6-methoxy-[1,3,5]triazin-2-yl]-5-methoxy-phenol
—— 3-Trimethylstannanyl-propionic acid [1-(2,4-dihydroxy-phenyl)-meth-(Z)-ylidene]-hydrazide 72958-14-6 C13H20N2O3Sn
3-Trimethylstannanyl-propionic acid [1-(2,4-dihydroxy-phenyl)-meth-(Z)-ylidene]-hydrazide
—— 4,4'-(1,5-dimethyl-1<i>H</i>-pyrazol-3-ylmethanediyl)-bis-phenol 16147-28-7 C18H18N2O2
4,4'-(1,5-dimethyl-1<i>H</i>-pyrazol-3-ylmethanediyl)-bis-phenol
—— 5-amino-3-oxo-1-phenyl-2,3-dihydro-1<i>H</i>-pyrazole-4-carbothioic acid (1,2-dihydroxy-benzylidene)-hydrazide 51244-82-7 C17H15N5O3S
5-amino-3-oxo-1-phenyl-2,3-dihydro-1<i>H</i>-pyrazole-4-carbothioic acid (1,2-dihydroxy-benzylidene)-hydrazide
—— N,N-Bis(2,4-dinitrophenyl) Derivative of Methyl α-Amino-(4-hydroxy-6-benzothiazolyl)propionate 73368-45-3 C23H16N6O11S
N,N-Bis(2,4-dinitrophenyl) Derivative of Methyl α-Amino-(4-hydroxy-6-benzothiazolyl)propionate
—— N-(2-Hydroxy-5-methyl-benzyliden)-m-methyl-anilin 19430-17-2 C15H15NO
N-(2-Hydroxy-5-methyl-benzyliden)-m-methyl-anilin
—— 2,4-dihydroxyphenyl 4-piperidinobutyl sulfide hydrochloride 126531-09-7 C15H23NO2S*ClH
2,4-dihydroxyphenyl 4-piperidinobutyl sulfide hydrochloride
—— 2,6-diiodo-4-octylphenol 643064-91-9 C14H20I2O
2,6-diiodo-4-octylphenol
—— Dipropylbis-(p-hydroxyphenyl)-silan 18054-15-4 C18H24O2Si
Dipropylbis-(p-hydroxyphenyl)-silan
—— 1-Methyl-2-phenyl-5-(4'-hydroxybenzyl)-imidazolin-4-on 52963-43-6 C17H16N2O2
1-Methyl-2-phenyl-5-(4'-hydroxybenzyl)-imidazolin-4-on
—— 1428637-05-1 C9H10ClNO3
—— (R)-2-(4-hydroxyphenoxy)propionic acid N-(2-pyrazinyl)amide 1097632-57-9 C13H13N3O3
(R)-2-(4-hydroxyphenoxy)propionic acid N-(2-pyrazinyl)amide
—— Tricyanphenol 52199-96-9 C13H11N3O3
Tricyanphenol
—— 6-Isopropyl-3-methyl-2,4-dinitro-phenol; compound with 2-amino-ethanol 43143-34-6 C2H7NO*C10H12N2O5
6-Isopropyl-3-methyl-2,4-dinitro-phenol; compound with 2-amino-ethanol
—— 4-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-benzene-1,3-diol 13413-68-8 C11H11N3O4
4-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-benzene-1,3-diol
—— 3-(2-Hydroxy-4-methoxyphenyl)-5-(2-pyridyl)-1,2-oxazol 36256-95-8 C15H12N2O3
3-(2-Hydroxy-4-methoxyphenyl)-5-(2-pyridyl)-1,2-oxazol
—— 2-(2-hydroxy-3,5-dinitrophenyl)pyridine 127527-00-8 C11H7N3O5
2-(2-hydroxy-3,5-dinitrophenyl)pyridine
—— 1-Salicylidencarbazoylacetyl-4-ethyl-thiosemicarbazid 55129-48-1 C13H17N5O3S
1-Salicylidencarbazoylacetyl-4-ethyl-thiosemicarbazid
—— 4-Benzyloxy-2-bromo-5-hydroxy-ω-nitrostyrene 40705-23-5 C15H12BrNO4
4-Benzyloxy-2-bromo-5-hydroxy-ω-nitrostyrene
—— 7-Chlor-5-methoxy-2-methylindol-pikrat 49710-52-3 C6H3N3O7*C10H10ClNO
7-Chlor-5-methoxy-2-methylindol-pikrat
—— o-Iodanilin-Dimethylpicrinsaeure-Komplex 51010-39-0 C6H6IN*C8H7N3O7
o-Iodanilin-Dimethylpicrinsaeure-Komplex
—— 3-nitro-4'-chloro-thionosalicylic acid anilide 23421-74-1 C13H9ClN2O3S
3-nitro-4'-chloro-thionosalicylic acid anilide