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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
—— 71313-81-0 C21H15Cl2N3O8
—— (E)-3'-hydroxy-4'-methoxyacetophenone O-2-fluorobenzyl oxime 1072708-92-9 C16H16FNO3
(E)-3'-hydroxy-4'-methoxyacetophenone O-2-fluorobenzyl oxime
—— 3,5-Dinitro-2-hydroxyphenylmethansulfonsaeurephenylester 66950-26-3 C13H10N2O8S
3,5-Dinitro-2-hydroxyphenylmethansulfonsaeurephenylester
—— [Zn(N,N'-bis(3-hydroxysalicylidene)-1,4-butanediamine(-2H))] 726696-05-5 C18H18N2O4Zn
[Zn(N,N'-bis(3-hydroxysalicylidene)-1,4-butanediamine(-2H))]
—— 4,7,20-Trioxa-1,10-diaza-tricyclo[8.7.5.1<sup>12,16</sup>]tricosa-12,14,16(23)-trien-23-ol; hydrobromide 144703-80-0 BrH*C18H28N2O4
4,7,20-Trioxa-1,10-diaza-tricyclo[8.7.5.1<sup>12,16</sup>]tricosa-12,14,16(23)-trien-23-ol; hydrobromide
—— (E)-3'-hydroxy-4'-methoxyacetophenone O-4-fluorobenzyl oxime 1072708-84-9 C16H16FNO3
(E)-3'-hydroxy-4'-methoxyacetophenone O-4-fluorobenzyl oxime
—— 2,4,6-Tri-(3-methyl)-butylresorcinol 25915-32-6 C21H36O2
2,4,6-Tri-(3-methyl)-butylresorcinol
—— triphenyl(2-methoxy-1-propenyl)arsonium iodide 118194-68-6 C22H22AsO*I
triphenyl(2-methoxy-1-propenyl)arsonium iodide
—— 7-[1-(2-hydroxy-ethyl)-3,5-dimethyl-1H-pyrazol-4-ylmethyl]-5-methyl-indan-4-ol 1092551-91-1 C18H24N2O2
7-[1-(2-hydroxy-ethyl)-3,5-dimethyl-1H-pyrazol-4-ylmethyl]-5-methyl-indan-4-ol
—— 7-methyloctyl 3-(4-hydroxy-3-methoxyphenyl)propionate 951221-89-9 C19H30O4
7-methyloctyl 3-(4-hydroxy-3-methoxyphenyl)propionate
—— 1370047-18-9 C13H22NO4P
—— 2,4,6-tripentylbenzene-1,3,5-triol 1027335-26-7 C21H36O3
2,4,6-tripentylbenzene-1,3,5-triol
—— 4-(2,3-Epoxy-propoxy)-2-(1,1,3,3-tetramethyl-butyl)-phenol 26205-18-5 C17H26O3
4-(2,3-Epoxy-propoxy)-2-(1,1,3,3-tetramethyl-butyl)-phenol
—— 1-(o-hydroxyphenyl)-3-cyclohexylpropargylic alcohol 1322775-85-8 C15H18O2
1-(o-hydroxyphenyl)-3-cyclohexylpropargylic alcohol
—— 4-Thiazolidinone, 5-((4-hydroxy-3-methoxyphenyl)methylene)-3-(((2-nitrophenyl)amino)methyl)-2-thioxo- 89752-54-5 C18H15N3O5S2
4-Thiazolidinone, 5-((4-hydroxy-3-methoxyphenyl)methylene)-3-(((2-nitrophenyl)amino)methyl)-2-thioxo-
—— 2-(2'-Hydroxy-5'-bromphenyl)-5-isobutylamino-1,3,4-thiadiazol 35314-05-7 C12H14BrN3OS
2-(2'-Hydroxy-5'-bromphenyl)-5-isobutylamino-1,3,4-thiadiazol
—— 2,4,6-Trimethyl-N-<5-chlor-salicyliden>-anilin 93010-79-8 C16H16ClNO
2,4,6-Trimethyl-N-<5-chlor-salicyliden>-anilin
—— 1186105-20-3 C30H33N5O3
—— methyl 3-[4-(indan-2-yloxy)-3-(1-methyl-1H-indazol-5-yl)phenyl]propionate 590415-73-9 C27H26N2O3
methyl 3-[4-(indan-2-yloxy)-3-(1-methyl-1H-indazol-5-yl)phenyl]propionate
—— isovanillyl 7-methyl nonanoate 1000377-99-0 C18H28O4
isovanillyl 7-methyl nonanoate
—— di-tert-butyl 5-bromo-2-hydroxyphenylphosphonate 137360-77-1 C14H22BrO4P
di-tert-butyl 5-bromo-2-hydroxyphenylphosphonate
—— 1-(3,5-bis(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethan-1-one 1344115-14-5 C17H16N2O3
1-(3,5-bis(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethan-1-one
—— 1398523-45-9 C15H11Br2ClN2O
—— <5-Hydroxy-2.4-dimethyl-phenyl>-phosphonsaeure-diaethylester 106274-20-8 C12H19O4P
<5-Hydroxy-2.4-dimethyl-phenyl>-phosphonsaeure-diaethylester
—— Benzyloxy-thiocarbonyl-hydrazon des p-Hydroxy-benzaldehyds 93733-22-3 C15H14N2O2S
Benzyloxy-thiocarbonyl-hydrazon des p-Hydroxy-benzaldehyds
—— 1389250-12-7 C11H10BrNO3
—— 2,4-bis(2,4-dihydroxyphenyl)-6-(4-bromophenyl)-1,3,5-triazine 122864-81-7 C21H14BrN3O4
2,4-bis(2,4-dihydroxyphenyl)-6-(4-bromophenyl)-1,3,5-triazine
—— <i>N</i>-<i>p</i>-tolyl-salicylamidine 107776-94-3 C14H14N2O
<i>N</i>-<i>p</i>-tolyl-salicylamidine
—— 2-Bromo-6-(5-furan-2-yl-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-phenol 75201-05-7 C14H13BrN2O2
2-Bromo-6-(5-furan-2-yl-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-phenol
—— 3-hydroxy-benzaldehyde-[3]pyridylimine 108676-24-0 C12H10N2O
3-hydroxy-benzaldehyde-[3]pyridylimine
—— 6-dodecyl-6-(2-hydroxybenzyl)-13,13-dimethyl-1,4,8,11-tetraoxacyclotetradecane 145761-54-2 C31H54O5
6-dodecyl-6-(2-hydroxybenzyl)-13,13-dimethyl-1,4,8,11-tetraoxacyclotetradecane
—— 2-[3-(4-chlorophenyl)-5-isoxazolyl]-4-{3-[3-(4-chlorophenyl)-5-isoxazolyl]-4-hydroxybenzyl}phenol 1179924-58-3 C31H20Cl2N2O4
2-[3-(4-chlorophenyl)-5-isoxazolyl]-4-{3-[3-(4-chlorophenyl)-5-isoxazolyl]-4-hydroxybenzyl}phenol
—— 4-Nitro-3,3,7-trimethyl-2-(2-hydroxy-3-nitrostyryl)indolenine 129431-65-8 C19H17N3O5
4-Nitro-3,3,7-trimethyl-2-(2-hydroxy-3-nitrostyryl)indolenine
—— 2-hydroxy-5-nitro-benzoic acid ethylidenehydrazide 99358-95-9 C9H9N3O4
2-hydroxy-5-nitro-benzoic acid ethylidenehydrazide
—— 5-salicylidenamino-3<i>H</i>-thiazole-2-thione 100872-79-5 C10H8N2OS2
5-salicylidenamino-3<i>H</i>-thiazole-2-thione
—— 3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole-5-carbonitrile 1448593-90-5 C16H13N3O
3-(4-hydroxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole-5-carbonitrile
—— 61931-83-7 C17H15N5NaO7S
—— 3,3'-((((1r,4r)-cyclohexane-1,4-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(benzene-1,2-diol) 674285-07-5 C20H22N2O4
3,3'-((((1r,4r)-cyclohexane-1,4-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(benzene-1,2-diol)
—— 4-Hydroxy-6-methyl-3-(endo-6-morpholino-cis-bicyclo<3.1.0>hex-6-yl)-2H-pyran-2-on 113087-14-2 C16H21NO4
4-Hydroxy-6-methyl-3-(endo-6-morpholino-cis-bicyclo<3.1.0>hex-6-yl)-2H-pyran-2-on
—— 5-(3-Hydroxypropyl)-5-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-ol 1415611-19-6 C15H22O2
5-(3-Hydroxypropyl)-5-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-ol
—— 2-(3-fluoro-2-hydroxyphenyl)-6-methyl-5-(2-methylpropyl)-3-(2-phenylethyl)-4(3H)-pyrimidinethione 938177-66-3 C23H25FN2OS
2-(3-fluoro-2-hydroxyphenyl)-6-methyl-5-(2-methylpropyl)-3-(2-phenylethyl)-4(3H)-pyrimidinethione
—— 5-(2-chloroethoxy)-1,3-bis((4-hydroxylethylphenoxy)methyl)benzene 1542505-54-3 C26H29ClO5
5-(2-chloroethoxy)-1,3-bis((4-hydroxylethylphenoxy)methyl)benzene
—— [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester 869476-96-0 C20H26O5
[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester
—— 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(3-methoxy-4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole 1257983-70-2 C19H15ClN2O4S
3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-(3-methoxy-4-hydroxyphenyl)-2,3-dihydro-1,3,4-oxadiazole
—— trans-2-Crotyl-6-methyl-phenol 22575-37-7 C11H14O
trans-2-Crotyl-6-methyl-phenol
—— N'1,N'3-bis(3,4,5-trihydroxybenzylidene)malonohydrazide 1622386-18-8 C17H16N4O8
N'1,N'3-bis(3,4,5-trihydroxybenzylidene)malonohydrazide
—— 5,6-diphenyl-3-(2'-hydroxyphenyl)-1,2,4-triazine 16086-60-5 C21H15N3O
5,6-diphenyl-3-(2'-hydroxyphenyl)-1,2,4-triazine
—— 2-heptyl-5-pentyl-3-tri(propan-2-yl)silyloxyphenol 114534-47-3 C27H50O2Si
2-heptyl-5-pentyl-3-tri(propan-2-yl)silyloxyphenol
—— Ni(II){4-(5-methyl-2-pyridylazo)resorcinol}2(2+) 102678-65-9 C24H22N6NiO4
Ni(II){4-(5-methyl-2-pyridylazo)resorcinol}2(2+)
—— 4-Hydroxy-3-methoxy-thiobenzoesaeure-hydrazid 92223-83-1 C8H10N2O2S
4-Hydroxy-3-methoxy-thiobenzoesaeure-hydrazid