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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
—— 5-methoxy-4-methyl-2-[4-(2-methyl-thiazol-4-yl)-isoxazol-3-yl]-phenol 66780-74-3 C15H14N2O3S
5-methoxy-4-methyl-2-[4-(2-methyl-thiazol-4-yl)-isoxazol-3-yl]-phenol
—— 3,5-dibromo-4-hydroxy-benzaldehyde-semicarbazone 104700-69-8 C8H7Br2N3O2
3,5-dibromo-4-hydroxy-benzaldehyde-semicarbazone
—— 3-{(E)-[(4-methylphenyl)imino]methyl}-4-nitrophenol 1252004-25-3 C14H12N2O3
3-{(E)-[(4-methylphenyl)imino]methyl}-4-nitrophenol
—— 1261386-16-6 C21H26Cl2N4O3
—— 2-[(E)-Cyclopentyliminomethyl]-4,6-diiodo-phenol 20099-21-2 C12H13I2NO
2-[(E)-Cyclopentyliminomethyl]-4,6-diiodo-phenol
—— (R)-1,3-dimethyl-5-p-tolyl-3,4-dihydroisoquinolin-8-ol 1257243-86-9 C18H19NO
(R)-1,3-dimethyl-5-p-tolyl-3,4-dihydroisoquinolin-8-ol
—— 5-Br-2-OH-C6H3CH=NC6F5 26672-09-3 C13H5BrF5NO
5-Br-2-OH-C6H3CH=NC6F5
—— N-(3-bromo-5-methoxysalicylidene)-3-[bis(5-methyl-2-furyl)methyl]aniline 1000414-99-2 C25H22BrNO4
N-(3-bromo-5-methoxysalicylidene)-3-[bis(5-methyl-2-furyl)methyl]aniline
—— 2-(4,6-dimethyl-[1,3,5]triazin-2-yl)-4-methyl-phenol 6773-28-0 C12H13N3O
2-(4,6-dimethyl-[1,3,5]triazin-2-yl)-4-methyl-phenol
—— 2-[2-[2-[(2-Hydroxy-3-methoxy-5-thiophen-2-ylphenyl)methylideneamino]ethyldisulfanyl]ethyliminomethyl]-6-methoxy-4-thiophen-2-ylphenol 1093119-69-7 C28H28N2O4S4
2-[2-[2-[(2-Hydroxy-3-methoxy-5-thiophen-2-ylphenyl)methylideneamino]ethyldisulfanyl]ethyliminomethyl]-6-methoxy-4-thiophen-2-ylphenol
—— (S)-4-(2,3-epoxypropoxy)phenol 730984-83-5 C9H10O3
(S)-4-(2,3-epoxypropoxy)phenol
—— N-(4-Hydroxy-phenyl)-N'-[1-methyl-pyrrolidin-(2E)-ylidene]-pyrrolidine-1-carboxamidine 75357-98-1 C16H22N4O
N-(4-Hydroxy-phenyl)-N'-[1-methyl-pyrrolidin-(2E)-ylidene]-pyrrolidine-1-carboxamidine
—— 2,6-Dinitro-4-(1-propylbutyl)-phenol 6465-62-9 C13H18N2O5
2,6-Dinitro-4-(1-propylbutyl)-phenol
—— N-(4-carboxybenzylidene)-2-hydroxy-4-nitroaniline 881010-51-1 C14H10N2O5
N-(4-carboxybenzylidene)-2-hydroxy-4-nitroaniline
—— 4,5-bis(4-(salicylideneimino)phenyl)-4',5'-(ethylenedithio)tetrathiafulvalene 1246173-48-7 C34H24N2O2S6
4,5-bis(4-(salicylideneimino)phenyl)-4',5'-(ethylenedithio)tetrathiafulvalene
—— 5,17-bis(aminodiethoxyphosphorylmethyl)-25,27-dipropoxycalix[4]arene 879885-84-4 C44H60N2O10P2
5,17-bis(aminodiethoxyphosphorylmethyl)-25,27-dipropoxycalix[4]arene
—— 4-(4-Hydroxy-phenyl)-7,9-diphenyl-1,2,6,8,9-pentaaza-spiro[4.5]deca-1,7-dien-10-one 82059-87-8 C23H19N5O2
4-(4-Hydroxy-phenyl)-7,9-diphenyl-1,2,6,8,9-pentaaza-spiro[4.5]deca-1,7-dien-10-one
—— 2,6-difluoro-4-[(E)-hydroxyiminomethyl]phenol 960287-97-2 C7H5F2NO2
2,6-difluoro-4-[(E)-hydroxyiminomethyl]phenol
—— 2-(4,5-dihydro-3<i>H</i>-pyrrol-2-yl)-4-methyl-phenol 7167-64-8 C11H13NO
2-(4,5-dihydro-3<i>H</i>-pyrrol-2-yl)-4-methyl-phenol
—— N'-{[2-hydroxy-5-methoxy-3-(3-methyl-2-butenyl)]phenylmethylene}-1H-benzo[d]imidazole-2-acethydrazide hydrochloride 1206789-65-2 C22H24N4O3*ClH
N'-{[2-hydroxy-5-methoxy-3-(3-methyl-2-butenyl)]phenylmethylene}-1H-benzo[d]imidazole-2-acethydrazide hydrochloride
—— 5,6-dimethyl-2-ethynyl-3-iodohydroquinone 223463-21-6 C10H9IO2
5,6-dimethyl-2-ethynyl-3-iodohydroquinone
—— 130147-57-8 C29H33N3O4
—— 1,1,1-trichloro-3-nitro-N-[1-(4,6-dimethyl-2-hydroxyphenyl)ethylidene]propan-2-amine 1033425-31-8 C13H15Cl3N2O3
1,1,1-trichloro-3-nitro-N-[1-(4,6-dimethyl-2-hydroxyphenyl)ethylidene]propan-2-amine
—— 4,8-Dihydroxy-cinnolin-5-sulfonsaeure-kaliumsalz 17750-13-9 C8H5N2O5S*K
4,8-Dihydroxy-cinnolin-5-sulfonsaeure-kaliumsalz
—— 4-[(1,9-ditert-butyl-3,7-dimethyl-5H-benzo[d][1,3,2]benzodioxaphosphocin-11-yl)oxy]-2,2,6,6-tetramethylpiperidine 99319-36-5 C32H48NO3P
4-[(1,9-ditert-butyl-3,7-dimethyl-5H-benzo[d][1,3,2]benzodioxaphosphocin-11-yl)oxy]-2,2,6,6-tetramethylpiperidine
—— 90963-49-8 C15H14BN3O4
—— Phenol, 2-bromo-6-[[(3-hydroxycyclohexyl)imino]methyl]-, cis- 54942-93-7 C13H16BrNO2
Phenol, 2-bromo-6-[[(3-hydroxycyclohexyl)imino]methyl]-, cis-
—— 2-methyl-5-(5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl)phenol 1033725-01-7 C14H11N3O2
2-methyl-5-(5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl)phenol
—— N-{2-[2-Hydroxy-2-(2-hydroxy-phenyl)-ethylamino]-ethyl}-isobutyramide 56443-20-0 C14H22N2O3
N-{2-[2-Hydroxy-2-(2-hydroxy-phenyl)-ethylamino]-ethyl}-isobutyramide
—— 2-methyl-4-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)phenol 42001-20-7 C16H23NO
2-methyl-4-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)phenol
—— 2-hydroxy-6-methoxy-3-methoxymethoxybenzaldehyde 160820-44-0 C10H12O5
2-hydroxy-6-methoxy-3-methoxymethoxybenzaldehyde
—— (2'S,4'R,6'S)-2'-(2''-thien-2'''-yl-ethyl)-6'-(4''''-hydroxyphenyl)tetrahydropyran-4'-yl acetate 1440430-72-7 C19H22O4S
(2'S,4'R,6'S)-2'-(2''-thien-2'''-yl-ethyl)-6'-(4''''-hydroxyphenyl)tetrahydropyran-4'-yl acetate
—— (1R,5S)-3-[2-ethyl-5-(furan-3-yl)phenyl]-4-hydroxybicyclo[3.2.1]oct-3-en-2-one 1090512-04-1 C20H20O3
(1R,5S)-3-[2-ethyl-5-(furan-3-yl)phenyl]-4-hydroxybicyclo[3.2.1]oct-3-en-2-one
—— 4-(2-Methoxy-6-hydroxyphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 130799-46-1 C16H18O3
4-(2-Methoxy-6-hydroxyphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one
—— 5-(3,4-dimethyl-phenyl)-2-methyl-thiazole-4-carboxylic acid cyclopropylmethyl-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide 1223584-55-1 C26H30N2O3S
5-(3,4-dimethyl-phenyl)-2-methyl-thiazole-4-carboxylic acid cyclopropylmethyl-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-amide
—— 8-hydroxy-7-methoxy-2,2',3,3'-tetrahydrospiro[benzo[d]azepine-1,1'-inden]-4(5H)-one 146471-00-3 C19H19NO3
8-hydroxy-7-methoxy-2,2',3,3'-tetrahydrospiro[benzo[d]azepine-1,1'-inden]-4(5H)-one
—— 4-isoxazol-5-ylphenol 502658-76-6 C9H7NO2
4-isoxazol-5-ylphenol
—— N-[2-(2-Bromo-3-hydroxy-4-methoxy-phenyl)-ethyl]-2-(3-hydroxy-4-methoxy-phenyl)-acetamide 96917-02-1 C18H20BrNO5
N-[2-(2-Bromo-3-hydroxy-4-methoxy-phenyl)-ethyl]-2-(3-hydroxy-4-methoxy-phenyl)-acetamide
—— 4-{5-[5-(4-bromophenyl)thiophen-2-yl]-1,3,4-thiadiazol-2-yl}benzene-1,3-diol 1447735-09-2 C18H11BrN2O2S2
4-{5-[5-(4-bromophenyl)thiophen-2-yl]-1,3,4-thiadiazol-2-yl}benzene-1,3-diol
—— 2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-4-iodo-6-methylphenol 1392406-70-0 C14H18IN5O
2-[4,6-Bis(dimethylamino)-1,3,5-triazin-2-yl]-4-iodo-6-methylphenol
—— N-benzyl-2-(4-hydroxy-3,5-dinitrophenyl)acetamide 1443011-80-0 C15H13N3O6
N-benzyl-2-(4-hydroxy-3,5-dinitrophenyl)acetamide
—— 2-[[4-[2-[3,4-Bis[(2-hydroxyphenyl)methylideneamino]phenyl]ethyl]-2-[(2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol 863134-80-9 C42H34N4O4
2-[[4-[2-[3,4-Bis[(2-hydroxyphenyl)methylideneamino]phenyl]ethyl]-2-[(2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol
—— 2-[4-(4-Hydroxymethyl-[1,2,3]triazol-1-yl)-pyrimidin-2-yl]-phenol 88236-24-2 C13H11N5O2
2-[4-(4-Hydroxymethyl-[1,2,3]triazol-1-yl)-pyrimidin-2-yl]-phenol
—— 1127228-41-4 C15H14N4O4S
—— 1,1'-[4-(2-hydroxy-benzylideneamino)-4<i>H</i>-[1,2,4]triazole-3,5-diyl]-bis-propan-2-one 33761-53-4 C15H16N4O3
1,1'-[4-(2-hydroxy-benzylideneamino)-4<i>H</i>-[1,2,4]triazole-3,5-diyl]-bis-propan-2-one
—— (R)-(-)-1-Acetoxy-2-(2-hydroxyphenyl)propane 96641-48-4 C11H14O3
(R)-(-)-1-Acetoxy-2-(2-hydroxyphenyl)propane
—— 2-{[(3-Methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino}ethane-1-sulfonic acid 548492-21-3 C10H13NO5S
2-{[(3-Methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]amino}ethane-1-sulfonic acid
—— N-benzyl-2-hydroxy-4-methoxy-benzenecarbothioamide 1132646-30-0 C15H15NO2S
N-benzyl-2-hydroxy-4-methoxy-benzenecarbothioamide
—— 1260402-97-8 C32H48O5Si
—— bis(2-hydroxy-5-methylphenyl)phenylphosphine 392685-60-8 C20H19O2P
bis(2-hydroxy-5-methylphenyl)phenylphosphine