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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
—— 1,2-Bis-<2,5-dihydroxy-3,4,6-trimethyl-phenyl>-aethan 17228-94-3 C20H26O4
1,2-Bis-<2,5-dihydroxy-3,4,6-trimethyl-phenyl>-aethan
—— 3,4-Dimethyl-6-isohexylphenol 13537-66-1 C14H22O
3,4-Dimethyl-6-isohexylphenol
—— 1,7-Bis(2-hydroxy-5-methylphenyl)heptan 10400-53-0 C21H28O2
1,7-Bis(2-hydroxy-5-methylphenyl)heptan
—— 2-(4-cyclohexyl-butyl)-hydroquinone 408310-34-9 C16H24O2
2-(4-cyclohexyl-butyl)-hydroquinone
—— 3-Ethylpyridazine;2,4,6-trinitrophenol 28200-52-4 C12H11N5O7
3-Ethylpyridazine;2,4,6-trinitrophenol
—— (3,4,5,6-Tetrachlor-2-hydroxy-phenylhydrazono)-malonsaeure-diaethylester 21103-98-0 C13H12Cl4N2O5
(3,4,5,6-Tetrachlor-2-hydroxy-phenylhydrazono)-malonsaeure-diaethylester
—— 16476-10-1 C16H16O8
—— [2-(1,2,3,4-thiatriazole-5-yliminomethyl)-phenol] 1263531-13-0 C8H6N4OS
[2-(1,2,3,4-thiatriazole-5-yliminomethyl)-phenol]
—— 3,9-bis(3-hydroxyphenyl)-2,4,8,10-tetrathiaspiro[5.5]undecane 1046827-40-0 C19H20O2S4
3,9-bis(3-hydroxyphenyl)-2,4,8,10-tetrathiaspiro[5.5]undecane
—— 4-Hydroxy-5-nitro-acetophenon-isonicotinoylhydrazon 797-10-4 C14H12N4O4
4-Hydroxy-5-nitro-acetophenon-isonicotinoylhydrazon
—— oxaldiimide-bis-(2-hydroxy-α-methyl-benzylidenehydrazide) 152167-20-9 C18H20N6O2
oxaldiimide-bis-(2-hydroxy-α-methyl-benzylidenehydrazide)
—— 2,5-diisobutyl-4-[2-(trimethylsilyl)ethyl]phenol 1230389-52-2 C19H34OSi
2,5-diisobutyl-4-[2-(trimethylsilyl)ethyl]phenol
—— 2,6-dihydroxynaphthalene-1,5-dithiol 120256-67-9 C10H8O2S2
2,6-dihydroxynaphthalene-1,5-dithiol
—— 4(e)-(2,5-Dihydroxyphenyl)cyclohexan-(e)-carbaldehyd 127572-74-1 C13H16O3
4(e)-(2,5-Dihydroxyphenyl)cyclohexan-(e)-carbaldehyd
—— 2-(4,5-dihydro-1H-imidazol-2-yl)-6-methylphenol 1788-05-2 C10H12N2O
2-(4,5-dihydro-1H-imidazol-2-yl)-6-methylphenol
—— 2-allyl-3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-4-methoxyphenol 1639236-88-6 C20H21N3O3
2-allyl-3-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)-4-methoxyphenol
—— (E)-sinapic acid 1403598-97-9 C12H14O5
(E)-sinapic acid
—— N,N-bis(2-methylthioethyl)-4-nitro-2-methylaminophenol 81992-17-8 C13H20N2O3S2
N,N-bis(2-methylthioethyl)-4-nitro-2-methylaminophenol
—— 4-sec-Hexyl-2-chlor-m-cresol 2502-77-4 C13H19ClO
4-sec-Hexyl-2-chlor-m-cresol
—— 1381771-77-2 C22H32N2O4
—— (5S,6R)-methyl 5-(4-hydroxy-3,5-dimethoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate 1239015-23-6 C18H20O7
(5S,6R)-methyl 5-(4-hydroxy-3,5-dimethoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate
—— N-[4-(4-hydroxy-3-methoxyphenyl)-1,3-thiazol-2-yl]acetamide 1426059-03-1 C12H12N2O3S
N-[4-(4-hydroxy-3-methoxyphenyl)-1,3-thiazol-2-yl]acetamide
—— N-cyano-N'-[(2-hydroxy-3-methoxyphenyl)methyl]propanimidamide 736946-73-9 C12H15N3O2
N-cyano-N'-[(2-hydroxy-3-methoxyphenyl)methyl]propanimidamide
—— 1-(1-adamantyl)-3-[(Z)-(4-hydroxy-3-methoxyphenyl)methylideneamino]urea 348590-58-9 C19H25N3O3
1-(1-adamantyl)-3-[(Z)-(4-hydroxy-3-methoxyphenyl)methylideneamino]urea
—— 2-[2-[[2-Hydroxy-3-[2-[(2-hydroxyphenyl)methylideneamino]ethylamino]propyl]amino]ethyliminomethyl]phenol 1261386-11-1 C21H28N4O3
2-[2-[[2-Hydroxy-3-[2-[(2-hydroxyphenyl)methylideneamino]ethylamino]propyl]amino]ethyliminomethyl]phenol
—— 4-[4-(2-hydroxy-phenyl)-6-methoxy-[1,3,5]triazin-2-yl]-benzene-1,3-diol 38358-88-2 C16H13N3O4
4-[4-(2-hydroxy-phenyl)-6-methoxy-[1,3,5]triazin-2-yl]-benzene-1,3-diol
—— 6-Amino-5-<(3-methoxy-4-hydroxy-benzyliden)-amino>-1,3-dimethyl-uracil 20886-64-0 C14H16N4O4
6-Amino-5-<(3-methoxy-4-hydroxy-benzyliden)-amino>-1,3-dimethyl-uracil
—— 3-Methyl-2-(nitromethyl)pyridine picrate 35624-31-8 C13H11N5O9
3-Methyl-2-(nitromethyl)pyridine picrate
—— 2-Dimethylaminomethyl-6-methoxy-4-acetamino-phenol 13885-94-4 C12H18N2O3
2-Dimethylaminomethyl-6-methoxy-4-acetamino-phenol
—— 4-<2-cyclohexyl-aethyl>-o-kresol 6800-91-5 C15H22O
4-<2-cyclohexyl-aethyl>-o-kresol
—— 2,4-Dinitro-phenol; compound with piperazine 93014-75-6 C4H10N2*C6H4N2O5
2,4-Dinitro-phenol; compound with piperazine
—— (4R)-4-hydroxy-4-(2-hydroxy-5-methoxy-phenyl)-butan-2-one 1162642-11-6 C11H14O4
(4R)-4-hydroxy-4-(2-hydroxy-5-methoxy-phenyl)-butan-2-one
—— 4-hydroxy-3-[5-(4-hydroxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-6-methyl-pyran-2-one 56364-36-4 C21H18N2O4
4-hydroxy-3-[5-(4-hydroxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-6-methyl-pyran-2-one
—— Salicylidendimalonitril 3905-04-2 C13H8N4O
Salicylidendimalonitril
—— tert-butyl [(3-hydroxybenzyl)sulfamoyl]carbamate 1295504-24-3 C12H18N2O5S
tert-butyl [(3-hydroxybenzyl)sulfamoyl]carbamate
—— bis-(4-hydroxy-benzyl)-carbamic acid tert-butyl ester 1267623-92-6 C19H23NO4
bis-(4-hydroxy-benzyl)-carbamic acid tert-butyl ester
—— 2-hydroxy-phenylmercury (1+); bromide 40248-49-5 C6H5BrHgO
2-hydroxy-phenylmercury (1+); bromide
—— 5,11,17-trimethyl-23-[12-(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)dodecyl]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 124028-45-1 C74H82O8
5,11,17-trimethyl-23-[12-(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)dodecyl]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
—— Tris-(3,5-dimethyl-4-hydroxy-benzyl)-isocyanurat 30458-75-4 C30H33N3O6
Tris-(3,5-dimethyl-4-hydroxy-benzyl)-isocyanurat
—— tBu-delta-PLH-2-OH-5-Br*TFA 714273-19-5 C2HF3O2*C19H19BrN4O3
tBu-delta-PLH-2-OH-5-Br*TFA
—— 2,6-diformyl-p-cresol-bis(4-o-tolyl thiosemicarbazone) 189126-14-5 C25H26N6OS2
2,6-diformyl-p-cresol-bis(4-o-tolyl thiosemicarbazone)
—— antimony(III) phloroglucinoxydichloride 92919-99-8 C6H5Cl2O3Sb
antimony(III) phloroglucinoxydichloride
—— ethyl (2R,3S)-3-(4-hydroxyphenyl)-2,3-bis[(2-hydroxyphenyl)methylideneamino]-2-methylpropanoate 1196042-05-3 C26H26N2O5
ethyl (2R,3S)-3-(4-hydroxyphenyl)-2,3-bis[(2-hydroxyphenyl)methylideneamino]-2-methylpropanoate
—— 3-(2'-Hydroxybenzyl)-2,4-pentandion 30881-26-6 C12H14O3
3-(2'-Hydroxybenzyl)-2,4-pentandion
—— (2E,4Z)-1-(2-hydroxy-4-methoxylphenyl)-4-methyl-5-phenylpenta-2,4-dien-1-one 1649448-00-9 C19H18O3
(2E,4Z)-1-(2-hydroxy-4-methoxylphenyl)-4-methyl-5-phenylpenta-2,4-dien-1-one
—— ethyl (2R,3S)-2,3-bis[(2-hydroxyphenyl)methylideneamino]-2-methyl-3-phenylpropanoate 1196042-00-8 C26H26N2O4
ethyl (2R,3S)-2,3-bis[(2-hydroxyphenyl)methylideneamino]-2-methyl-3-phenylpropanoate
—— 2-[[6-[(2-Hydroxy-3-methylphenyl)iminomethyl]pyridin-2-yl]methylideneamino]-6-methylphenol 934268-44-7 C21H19N3O2
2-[[6-[(2-Hydroxy-3-methylphenyl)iminomethyl]pyridin-2-yl]methylideneamino]-6-methylphenol
—— 6-(2-hydroxy-phenyl)-hexanoic acid hydrazide 100317-06-4 C12H18N2O2
6-(2-hydroxy-phenyl)-hexanoic acid hydrazide
—— 17646-42-3 C14H9FN4O2S
—— 3-cyano-4,6-diamino-5-(o-hydroxy)benzylidine-2-pyridothione 105774-84-3 C13H10N4OS
3-cyano-4,6-diamino-5-(o-hydroxy)benzylidine-2-pyridothione