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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
—— Brenzkatechin 344241-46-9 C6H6O2
Brenzkatechin
—— (-)-2-[(1R,2S,3R)-3-hydroxy-1,2-dimethylcyclopentyl]-4-methylphenol 681035-75-6 C14H20O2
(-)-2-[(1R,2S,3R)-3-hydroxy-1,2-dimethylcyclopentyl]-4-methylphenol
—— Tert-butyl (4-(3-hydroxyphenyl)but-3-yn-1-yl)carbamate 905293-42-7 C15H19NO3
Tert-butyl (4-(3-hydroxyphenyl)but-3-yn-1-yl)carbamate
—— (2E,4E)-N-benzyl-5-(3,4-dihydroxyphenyl)penta-2,4-dienamide 878800-19-2 C18H17NO3
(2E,4E)-N-benzyl-5-(3,4-dihydroxyphenyl)penta-2,4-dienamide
—— (S)-tert-butyl(2-hydroxyphenyl)methylphosphine 869585-59-1 C11H17OP
(S)-tert-butyl(2-hydroxyphenyl)methylphosphine
—— 2-[(4-Fluorophenyl)methylideneamino]-5-methylphenol 898289-36-6 C14H12FNO
2-[(4-Fluorophenyl)methylideneamino]-5-methylphenol
—— I+/-,3-Dihydroxybenzenemethanesulfonic acid 744954-43-6 C7H8O5S
I+/-,3-Dihydroxybenzenemethanesulfonic acid
—— Phenol, 4-amino-2,6-dimethoxy-, hydrochloride 198134-83-7 C8H12ClNO3
Phenol, 4-amino-2,6-dimethoxy-, hydrochloride
—— 2-amino-4-(2-hydroxy-5-methylphenyl)thiazole 103037-98-5 C10H10N2OS
2-amino-4-(2-hydroxy-5-methylphenyl)thiazole
—— 2-[(cyclohexylmethyl)amino]-5-(2-hydroxyphenyl)-1,3-thiazol-4(5H)-one 870707-69-0 C16H20N2O2S
2-[(cyclohexylmethyl)amino]-5-(2-hydroxyphenyl)-1,3-thiazol-4(5H)-one
—— 1,3-Benzenediol, 4,6-bis[(2,2-dimethylpropyl)amino]- 649767-95-3 C16H28N2O2
1,3-Benzenediol, 4,6-bis[(2,2-dimethylpropyl)amino]-
—— 2,8,14,20-Tetraoctylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 134724-39-3 C60H88O8
2,8,14,20-Tetraoctylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— 3-(1-Hydroxybut-3-ynyl)phenol 132927-16-3 C10H10O2
3-(1-Hydroxybut-3-ynyl)phenol
—— 5-[5-[3,5-Bis[5-(3,5-dihydroxyphenoxy)pentoxy]phenoxy]pentoxy]benzene-1,3-diol 461055-44-7 C39H48O12
5-[5-[3,5-Bis[5-(3,5-dihydroxyphenoxy)pentoxy]phenoxy]pentoxy]benzene-1,3-diol
—— methyl (E)-4-[(4-hydroxybenzyloxy)imino]-4-phenylbutyrate 250602-89-2 C18H19NO4
methyl (E)-4-[(4-hydroxybenzyloxy)imino]-4-phenylbutyrate
—— 1-benzofuran-2-carbaldehyde[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]hydrazone 1427161-68-9 C19H15N3O3S
1-benzofuran-2-carbaldehyde[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]hydrazone
—— 1-Tert-butyl-3-[(2-hydroxyphenyl)methylideneamino]thiourea 883036-77-9 C12H17N3OS
1-Tert-butyl-3-[(2-hydroxyphenyl)methylideneamino]thiourea
—— 3-chloro-2,4-dinitro-phenol 100367-63-3 C6H3ClN2O5
3-chloro-2,4-dinitro-phenol
—— 4-[2-({3-[(2S)-2-benzyloxy-4-(4-methoxyphenoxy)-2-methylbutyl]furan-2-yl}dimethylsilanyl)ethoxy]-2,3,5,6-tetrabromophenol 915769-91-4 C33H36Br4O6Si
4-[2-({3-[(2S)-2-benzyloxy-4-(4-methoxyphenoxy)-2-methylbutyl]furan-2-yl}dimethylsilanyl)ethoxy]-2,3,5,6-tetrabromophenol
—— 5-propyl-benzene-1,2,4-triol 198203-80-4 C9H12O3
5-propyl-benzene-1,2,4-triol
—— 6-Nitro-3-hydroxy-1-propyl-benzol 872272-42-9 C9H11NO3
6-Nitro-3-hydroxy-1-propyl-benzol
—— 5-{4-[3,5-Bis(4-bromobutoxy)phenoxy]butoxy}benzene-1,3-diol 63605-00-5 C24H32Br2O6
5-{4-[3,5-Bis(4-bromobutoxy)phenoxy]butoxy}benzene-1,3-diol
—— (S)-2,4-dimethoxy-3-methyl-6-p-tolylsulfinylphenol 613236-71-8 C16H18O4S
(S)-2,4-dimethoxy-3-methyl-6-p-tolylsulfinylphenol
—— 2-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]phenolate 2780-47-4 C14H13NO3
2-[(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylamino]phenolate
—— N-benzyl-5-chloro-2-hydroxybenzothioamide 1132646-18-4 C14H12ClNOS
N-benzyl-5-chloro-2-hydroxybenzothioamide
—— 2-heptyl-phloroglucinol 96756-20-6 C13H20O3
2-heptyl-phloroglucinol
—— 1-(2-hydroxy-5-methylbenzyl)-3-methylurea 1141461-08-6 C10H14N2O2
1-(2-hydroxy-5-methylbenzyl)-3-methylurea
—— 2-Cyano-5-methyl-hydrochinon 40930-87-8 C8H7NO2
2-Cyano-5-methyl-hydrochinon
—— methyl (2R)-2-(3-fluoro-4-hydroxyphenyl)propanoate 1370408-73-3 C10H11FO3
methyl (2R)-2-(3-fluoro-4-hydroxyphenyl)propanoate
—— ethyl 2-(3-fluoro-4-hydroxyphenyl)acetate 259543-80-1 C10H11FO3
ethyl 2-(3-fluoro-4-hydroxyphenyl)acetate
—— 4-(3-methyl-3-butenyl)phenol 18272-69-0 C11H14O
4-(3-methyl-3-butenyl)phenol
—— N-(5-Chloropyridin-2-yl)-5-hydroxy-2-nitrobenzamide 1616693-62-9 C12H8ClN3O4
N-(5-Chloropyridin-2-yl)-5-hydroxy-2-nitrobenzamide
—— (2S,8S,14R,20R)-2,8,14,20-tetrakis(2-methylpropyl)-5,11,17-tris(prop-2-enoxymethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol 1469921-92-3 C56H74O11
(2S,8S,14R,20R)-2,8,14,20-tetrakis(2-methylpropyl)-5,11,17-tris(prop-2-enoxymethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol
—— 2-Hydroxy-5-nitro-benzoyl Thiosemicarbazide 65043-12-1 C8H8N4O4S
2-Hydroxy-5-nitro-benzoyl Thiosemicarbazide
—— N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(4-hydroxy-3-nitrophenyl)acetamide 185104-75-0 C30H28N2O6
N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(4-hydroxy-3-nitrophenyl)acetamide
—— (1-(2-hydroxy)-phenyl)-N,N,N',N'-tetramethyl phosphonic diamide 112135-33-8 C10H17N2O2P
(1-(2-hydroxy)-phenyl)-N,N,N',N'-tetramethyl phosphonic diamide
—— N-octyl-4-hydroxy-3-nitrophenylacetamide 149555-55-5 C16H24N2O4
N-octyl-4-hydroxy-3-nitrophenylacetamide
—— 2-(4-hydroxy-3-nitrophenyl)-N,N-dipropylacetamide 101389-55-3 C14H20N2O4
2-(4-hydroxy-3-nitrophenyl)-N,N-dipropylacetamide
—— 1-(3-hydroxyphenyl)cyclopropanecarbonitrile 940307-96-0 C10H9NO
1-(3-hydroxyphenyl)cyclopropanecarbonitrile
—— 26-Amino-5,11,17,23-tetratert-butylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,27-diol 141081-98-3 C44H57NO2
26-Amino-5,11,17,23-tetratert-butylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,27-diol
—— 2-Allyl-3-{(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-5-methoxy-6-methyl-benzene-1,4-diol 717916-74-0 C35H64O6Si2
2-Allyl-3-{(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-5-methoxy-6-methyl-benzene-1,4-diol
—— 2-hydroxy-phenylmercury (1+); iodide 23000-08-0 C6H5HgIO
2-hydroxy-phenylmercury (1+); iodide
—— 2-hydroxy-3,5-dinitrobutyrophenone 91991-99-0 C10H10N2O6
2-hydroxy-3,5-dinitrobutyrophenone
—— 2-(heptan-4-yl)phenol 17404-43-2 C13H20O
2-(heptan-4-yl)phenol
—— 4-(1,4,5,6-tetrahydro-pyridazin-3-yl)-phenol 28858-18-6 C10H12N2O
4-(1,4,5,6-tetrahydro-pyridazin-3-yl)-phenol
—— 4,4'-(4-ethylisoxazole-3,5-diyl)diphenol 234093-08-4 C17H15NO3
4,4'-(4-ethylisoxazole-3,5-diyl)diphenol
—— 4-(4-decyl)phenol 17511-55-6 C16H26O
4-(4-decyl)phenol
—— 4-(4,5-dihydro-3<i>H</i>-pyrrol-2-yl)-phenol 7182-48-1 C10H11NO
4-(4,5-dihydro-3<i>H</i>-pyrrol-2-yl)-phenol
—— 2-Hydroxy-5-nitrobenzylcyanide 129295-69-8 C8H6N2O3
2-Hydroxy-5-nitrobenzylcyanide
—— 4-nitro-2-(sulfanylmethyl)phenol 140920-74-7 C7H7NO3S
4-nitro-2-(sulfanylmethyl)phenol