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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-decyl-6-phenyl-[1,3,5]triazin-2-yl)-phenol 5206-66-6 C25H31N3O
2-(4-decyl-6-phenyl-[1,3,5]triazin-2-yl)-phenol
—— 4,6-di-O-acetyl-3-O-(N-2,4-dimethoxybenzyl)carbamoyl-D-glucal 1133981-95-9 C20H25NO9
4,6-di-O-acetyl-3-O-(N-2,4-dimethoxybenzyl)carbamoyl-D-glucal
—— C6H2(OH)2(NCH2CH2NMe2)2 1267610-98-9 C18H30N4O2
C6H2(OH)2(NCH2CH2NMe2)2
—— Benzenemethanol,2-hydroxy-5-methoxy-a-methyl-a-(2-methyl-1-propenyl)- 88252-67-9 C13H18O3
Benzenemethanol,2-hydroxy-5-methoxy-a-methyl-a-(2-methyl-1-propenyl)-
—— 3-Hydroxy-4-(3-hydroxy-benzoyl)-5-(2-hydroxy-phenyl)-5H-furan-2-one 287729-34-4 C17H12O6
3-Hydroxy-4-(3-hydroxy-benzoyl)-5-(2-hydroxy-phenyl)-5H-furan-2-one
—— 2,6-Bis-acetoxymethyl-4-nitro-phenol 108541-31-7 C12H13NO7
2,6-Bis-acetoxymethyl-4-nitro-phenol
—— 4-(4-hydroxyphenyl)-3-methylthiazole-2(3H)-thione 1398409-75-0 C10H9NOS2
4-(4-hydroxyphenyl)-3-methylthiazole-2(3H)-thione
—— 1-(2-hydroxy-5-methoxybenzoyl)-3-{4-[(imino(thien-2-yl)methyl)amino]phenoxy}azetidine Hydrochloride 218944-83-3 C22H21N3O4S*ClH
1-(2-hydroxy-5-methoxybenzoyl)-3-{4-[(imino(thien-2-yl)methyl)amino]phenoxy}azetidine Hydrochloride
—— 2-deoxy-2-salicylideneamino-β-D-glucose 51471-41-1 C13H17NO6
2-deoxy-2-salicylideneamino-β-D-glucose
—— benzyl hydrogen (5-bromo-2-hydroxybenzylidene)carbonohydrazonodithioate 85429-61-4 C15H13BrN2OS2
benzyl hydrogen (5-bromo-2-hydroxybenzylidene)carbonohydrazonodithioate
—— 4-methoxy-2-(pyrrolidin-1-ylmethyleneamino)phenol 1323158-63-9 C12H16N2O2
4-methoxy-2-(pyrrolidin-1-ylmethyleneamino)phenol
—— 2-(5-(tert-butyldimethylsilyloxy)-1-hydroxypent-2-ynyl)phenol 1599371-35-3 C17H26O3Si
2-(5-(tert-butyldimethylsilyloxy)-1-hydroxypent-2-ynyl)phenol
—— 2-Amino-3-(4-hydroxy-phenyl)-<2-<sup>14</sup>C>-propionsaeure 4780-09-0 C9H11NO3
2-Amino-3-(4-hydroxy-phenyl)-<2-<sup>14</sup>C>-propionsaeure
—— MoO2(salicylaldehyde 4-methylthiosemicarbazone-2H) 866926-03-6 C9H9N3OS*MoO2
MoO2(salicylaldehyde 4-methylthiosemicarbazone-2H)
—— 3-[1-(3-hydroxy-phenylimino)-ethyl]-dihydro-furan-2-one 64745-33-1 C12H13NO3
3-[1-(3-hydroxy-phenylimino)-ethyl]-dihydro-furan-2-one
—— 4,4'-decanediyl-di-pyrogallol 10550-68-2 C22H30O6
4,4'-decanediyl-di-pyrogallol
—— 4-Hydroxy-3.5-dimethoxy-3'.5'-dichlor-4'-acetoxy-diphenylamin 97212-82-3 C16H15Cl2NO5
4-Hydroxy-3.5-dimethoxy-3'.5'-dichlor-4'-acetoxy-diphenylamin
—— 2-(benzenesulfonylmethyl)-3,5-dinitrophenol 92241-34-4 C13H10N2O7S
2-(benzenesulfonylmethyl)-3,5-dinitrophenol
—— 3-methyl-4-hydroxyphenyltellurium trichloride 78083-57-5 C7H7Cl3OTe
3-methyl-4-hydroxyphenyltellurium trichloride
—— 1,1-bis[2-{5-(4-hydroxy-3-methoxy)benzylidene-2-phenyl-1,3-thiazolidin-4-one}-1,3,4-thiadiazo-5-yl]cyclopropane 1362684-93-2 C41H32N6O6S4
1,1-bis[2-{5-(4-hydroxy-3-methoxy)benzylidene-2-phenyl-1,3-thiazolidin-4-one}-1,3,4-thiadiazo-5-yl]cyclopropane
—— 2-Benzyl-4-fluoro-5-methyl-phenol 13396-37-7 C14H13FO
2-Benzyl-4-fluoro-5-methyl-phenol
—— 2-(3-{3-[4-(2-hydroxyethyl)phenoxy]2(S)-hydroxypropoxy}-benzyl)tetrahydro-2-furancarboxylic acid 499788-63-5 C23H28O7
2-(3-{3-[4-(2-hydroxyethyl)phenoxy]2(S)-hydroxypropoxy}-benzyl)tetrahydro-2-furancarboxylic acid
—— N'-(4-Hydroxy-3-methoxybenzylidene)-2-(4-propylphenoxy)acetohydrazide 303084-73-3 C19H22N2O4
N'-(4-Hydroxy-3-methoxybenzylidene)-2-(4-propylphenoxy)acetohydrazide
—— N'-[(E)-(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]benzohydrazide 302910-13-0 C15H13BrN2O3
N'-[(E)-(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]benzohydrazide
—— 93319-82-5 C17H14BrN3O4
—— 4-(3,4-dihydroxy-benzylidene)-3-phenyl-4<i>H</i>-isoxazol-5-one 101727-53-1 C16H11NO4
4-(3,4-dihydroxy-benzylidene)-3-phenyl-4<i>H</i>-isoxazol-5-one
—— 4-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenol 217482-84-3 C17H20O7S
4-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenol
—— 5-(4-hydroxy-3,5-dimethyl-benzylidene)-3-(1-methyl-cyclohexylmethyl)-thiazolidine-2,4-dione 1185391-39-2 C20H25NO3S
5-(4-hydroxy-3,5-dimethyl-benzylidene)-3-(1-methyl-cyclohexylmethyl)-thiazolidine-2,4-dione
—— 3-Chlor-salicylaldehyd-(2-brom-ethylimin) 90887-54-0 C9H9BrClNO
3-Chlor-salicylaldehyd-(2-brom-ethylimin)
—— 4-Hydroxybenzaldehyde 2-(2,5-dihydro-5-thioxo-1H-1,2,4-triazol-3-yl)hydrazone 827588-95-4 C9H9N5OS
4-Hydroxybenzaldehyde 2-(2,5-dihydro-5-thioxo-1H-1,2,4-triazol-3-yl)hydrazone
—— 3-chloro-2-nitro-6-pentyl-phenol 105907-45-7 C11H14ClNO3
3-chloro-2-nitro-6-pentyl-phenol
—— 2-allyl-4-(3-hydroxypropyl)-6-methoxyphenol 854664-22-5 C13H18O3
2-allyl-4-(3-hydroxypropyl)-6-methoxyphenol
—— 1240360-84-2 C23H24N2O4S
—— N-[1-(2-hydroxy-3-nitrophenyl)ethylideneamino]-2-methylbenzamide 1235578-06-9 C16H15N3O4
N-[1-(2-hydroxy-3-nitrophenyl)ethylideneamino]-2-methylbenzamide
—— 1-(3-Brom-5-fluor-2-hydroxy-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-prop-2-enon-(2,4-dinitro-phenylhydrazon) 1826-90-0 C22H16BrFN4O7
1-(3-Brom-5-fluor-2-hydroxy-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-prop-2-enon-(2,4-dinitro-phenylhydrazon)
—— 3-Methoxy-2-isoamyloxyphenol 100520-86-3 C12H18O3
3-Methoxy-2-isoamyloxyphenol
—— 3,3'-dihydroxy-1,1'-<i>m</i>-xylylene-bis-pyridinium; dibromide 110491-61-7 2Br*C18H18N2O2
3,3'-dihydroxy-1,1'-<i>m</i>-xylylene-bis-pyridinium; dibromide
—— 5-(4-aminopyrimidin-2-ylamino)-2-methylphenol 933045-96-6 C11H12N4O
5-(4-aminopyrimidin-2-ylamino)-2-methylphenol
—— vanillin-(2-nitro-phenylhydrazone) 19263-89-9 C14H13N3O4
vanillin-(2-nitro-phenylhydrazone)
—— (R)-2-(2-hydroxy-5-methoxyphenylamino)-thiazoline-4-carboxylic acid hydrochloride 1334385-96-4 C11H12N2O4S*ClH
(R)-2-(2-hydroxy-5-methoxyphenylamino)-thiazoline-4-carboxylic acid hydrochloride
—— 2,5-Bis-<4-hydroxy-3,5-dimethyl-benzyliden>-cyclopentanon 27060-70-4 C23H24O3
2,5-Bis-<4-hydroxy-3,5-dimethyl-benzyliden>-cyclopentanon
—— 6,16,22,30-tetrahydroxy<3.3.3.3>metacyclophane 299205-57-5 C36H40O4
6,16,22,30-tetrahydroxy<3.3.3.3>metacyclophane
—— sodium trans-4-[N-(2'-hydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylate 81519-09-7 C15H18NO3*Na
sodium trans-4-[N-(2'-hydroxybenzylidene)aminomethyl]cyclohexane-1-carboxylate
—— (E)-N'-(5-chloro-2-hydroxy-benzylidene)acetohydrazide 1193731-87-1 C9H9ClN2O2
(E)-N'-(5-chloro-2-hydroxy-benzylidene)acetohydrazide
—— 4-[4-(4-hydroxy-3-methoxy-phenyl)-[1,3]dithietan-2-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 57624-75-6 C19H16N2O3S2
4-[4-(4-hydroxy-3-methoxy-phenyl)-[1,3]dithietan-2-ylidene]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one
—— 1357168-29-6 C15H18O5
—— N'-(2-hydroxy-5-nitrobenzylidene)-1H-pyrrole-2-carbohydrazide 929684-59-3 C12H10N4O4
N'-(2-hydroxy-5-nitrobenzylidene)-1H-pyrrole-2-carbohydrazide
—— cyclohexylmethyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate 1193988-31-6 C22H32N2O5
cyclohexylmethyl 4-(4-hydroxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate
—— Adrenalin 93117-67-0 C9H13NO3
Adrenalin
—— 4,6,10,12,16,18,22,24-octahydroxy-5-[N-(2,2-dimethyl-3-oxoprop-1-yl)ethylamino-methyl]-2,8,14,20-tetrapentylpentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene 1239171-47-1 C56H79NO9
4,6,10,12,16,18,22,24-octahydroxy-5-[N-(2,2-dimethyl-3-oxoprop-1-yl)ethylamino-methyl]-2,8,14,20-tetrapentylpentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene