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内酯类

内酯类化合物是一类含有环状结构的化合物,通常通过一个碳氧双键将两个羟基连接在一个四元、五元或六元的内环中形成。这类化合物广泛存在于自然界中,并且在有机化学、化学化工以及生物医药领域有着重要的应用价值。

内酯的分类
  1. 按环大小划分:根据内酯环的大小,可以将其分为四元、五元和六元内酯。
  2. 按碳原子数划分:依据组成内酯的碳原子数量不同,可进一步划分为二、三、四等碳链长度不同的内酯。
结构特征
  • 内酯结构中通常包含一个或多个环状氧基团。其独特的环状结构使得它们在水溶液中能够以开环形式存在。
  • 在生物体内,某些内酯通过酶的催化作用可实现快速转化,在药物设计和研究领域具有重要应用价值。
应用
  1. 医药领域:许多抗生素、抗真菌药及抗癌药物都含有内酯结构。例如,四环素类抗生素就含有五元或六元内酯。
  2. 工业化学:内酯作为重要的化工原料,在合成树脂、塑料和涂料等领域有着广泛应用。
  3. 分析化学与生物传感器:利用内酯的可逆开环性质进行分析检测;通过构建特定识别分子对提高生物传感系统的特异性。
生物活性
  • 内酯化合物通常具有一定的药理活性,如抗炎、抗菌等作用。这与其独特的空间构象和极性有关。
  • 在细胞信号传导过程中,内酯的环开裂或闭合可以影响特定蛋白质之间的相互作用。

总之,内酯作为一种重要的化学结构单元,在多个领域发挥着不可替代的作用。

中文名称 英文名称 CAS号 化学式 结构式图片
—— 2-methoxy-5-methylidene-N-propan-2-yloxolan-3-amine;5-methoxy-4-(propan-2-ylamino)oxolan-2-one —— C17H32N2O5
2-methoxy-5-methylidene-N-propan-2-yloxolan-3-amine;5-methoxy-4-(propan-2-ylamino)oxolan-2-one
—— 3,10-Dimethyl-8-oxatricyclo[4.3.1.03,10]decan-9-one —— C11H16O2
3,10-Dimethyl-8-oxatricyclo[4.3.1.03,10]decan-9-one
—— (1,8-Dimethyl-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-6-yl) 2,2-dimethylpropanoate;ethane —— C19H32O4
(1,8-Dimethyl-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-6-yl) 2,2-dimethylpropanoate;ethane
—— 4-Methoxy-1-methyl-3-(2-phenylethyl)-6-oxabicyclo[3.2.1]oct-2-en-7-one —— C17H20O3
4-Methoxy-1-methyl-3-(2-phenylethyl)-6-oxabicyclo[3.2.1]oct-2-en-7-one
—— 5-(1,3-Dioxolan-2-ylmethyl)oxolan-2-one —— C8H12O4
5-(1,3-Dioxolan-2-ylmethyl)oxolan-2-one
—— (5R)-5-ethyl-3-prop-2-enyloxolane-2,4-dione —— C9H12O3
(5R)-5-ethyl-3-prop-2-enyloxolane-2,4-dione
—— (3S,4R,5S,6R)-5-ethyl-4-hydroxy-3,6-dimethyloxan-2-one —— C9H16O3
(3S,4R,5S,6R)-5-ethyl-4-hydroxy-3,6-dimethyloxan-2-one
—— methyl 6-(4-bromophenyl)-3,5,5-trimethyl-2,4-dioxotetrahydro-2H-pyran-3-carboxylate —— C16H17BrO5
methyl 6-(4-bromophenyl)-3,5,5-trimethyl-2,4-dioxotetrahydro-2H-pyran-3-carboxylate
—— (1R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-4-ene-15,5'-oxolane]-2',7-dione —— C24H30O3
(1R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-4-ene-15,5'-oxolane]-2',7-dione
—— (4R,6R)-4-(hydroxymethyl)-6-[(1R,6R)-6-methoxy-3-methyl-1-tri(propan-2-yl)silyloxynona-2,4-dienyl]oxan-2-one —— C26H48O5Si
(4R,6R)-4-(hydroxymethyl)-6-[(1R,6R)-6-methoxy-3-methyl-1-tri(propan-2-yl)silyloxynona-2,4-dienyl]oxan-2-one
—— 5-[2-(2,2-Dimethoxyethyl)-1,3-dioxolan-4-yl]-3-hydroxyoxolane-2,4-dione —— C11H16O8
5-[2-(2,2-Dimethoxyethyl)-1,3-dioxolan-4-yl]-3-hydroxyoxolane-2,4-dione
—— 4-Methyl-5-pentyloxolane-2,3-dione —— C10H16O3
4-Methyl-5-pentyloxolane-2,3-dione
—— 5-(1,2-Dihydroxyethyl)-4-hydroxy-5-methyloxolane-2,3-dione —— C7H10O6
5-(1,2-Dihydroxyethyl)-4-hydroxy-5-methyloxolane-2,3-dione
—— 2-[(4-Isoamyl-5-keto-tetrahydrofuran-2-yl)methyl]isothiourea;hydrobromide —— C11H20N2O2S
2-[(4-Isoamyl-5-keto-tetrahydrofuran-2-yl)methyl]isothiourea;hydrobromide
—— [1-(4-Benzyl-5-oxooxolan-2-yl)ethylideneamino]urea —— C14H17N3O3
[1-(4-Benzyl-5-oxooxolan-2-yl)ethylideneamino]urea
—— [1-(4-Ethyl-5-oxooxolan-2-yl)ethylideneamino]urea —— C9H15N3O3
[1-(4-Ethyl-5-oxooxolan-2-yl)ethylideneamino]urea
—— [1-[4-(2-Methylpropyl)-5-oxooxolan-2-yl]ethylideneamino]urea —— C11H19N3O3
[1-[4-(2-Methylpropyl)-5-oxooxolan-2-yl]ethylideneamino]urea
—— 5-(1-hydroxy-ethyl)-5-methyl-3-(3-methyl-butyl)-dihydro-furan-2-one 29739-36-4 C12H22O3
5-(1-hydroxy-ethyl)-5-methyl-3-(3-methyl-butyl)-dihydro-furan-2-one
—— [1-(5-Oxo-4-phenyloxolan-2-yl)ethylideneamino]urea —— C13H15N3O3
[1-(5-Oxo-4-phenyloxolan-2-yl)ethylideneamino]urea
—— 3-Cyclopentylsulfanyl-2-(cyclopentylsulfanylmethyl)-4,5-dioxooxolane-2-carboxylic acid —— C16H22O5S2
3-Cyclopentylsulfanyl-2-(cyclopentylsulfanylmethyl)-4,5-dioxooxolane-2-carboxylic acid
—— (4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-8-methoxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-[tert-butyl(dimethyl)silyl]oxyoxan-2-one;bromo(trimethyl)silane —— C29H53BrO4Si2
(4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-8-methoxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-[tert-butyl(dimethyl)silyl]oxyoxan-2-one;bromo(trimethyl)silane
—— (3R,5S)-5-(2-phenylethyl)-3-prop-2-ynyloxolan-2-one —— C15H16O2
(3R,5S)-5-(2-phenylethyl)-3-prop-2-ynyloxolan-2-one
—— (7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienal —— C18H28O4
(7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienal
—— 3-Chloro-6-(3-cyclohexylpropyl)-6-cyclopentyloxane-2,4-dione —— C19H29ClO3
3-Chloro-6-(3-cyclohexylpropyl)-6-cyclopentyloxane-2,4-dione
—— [(1S,3S,7R,8R,8aS)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methyl-4,4-bis(trimethylsilyl)butanoate —— C30H52O5Si2
[(1S,3S,7R,8R,8aS)-8-[2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2R)-2-methyl-4,4-bis(trimethylsilyl)butanoate
—— 4,4-Dimethyl-3,5-dioxooxolane-2-carbaldehyde —— C7H8O4
4,4-Dimethyl-3,5-dioxooxolane-2-carbaldehyde
—— 6-(3-Cyclohexylpropyl)-6-cyclopentyloxane-2,4-dione —— C19H30O3
6-(3-Cyclohexylpropyl)-6-cyclopentyloxane-2,4-dione
—— (3R,5R,6R)-6-but-1-enyl-3,5-dimethyloxan-2-one —— C11H18O2
(3R,5R,6R)-6-but-1-enyl-3,5-dimethyloxan-2-one
—— 1-Propyl-7-sulfanylidene-1,4,4a,5,6,8,9,9a-octahydroindeno[2,1-c]pyran-3-one —— C15H20O2S
1-Propyl-7-sulfanylidene-1,4,4a,5,6,8,9,9a-octahydroindeno[2,1-c]pyran-3-one
—— (1S,2S,4R,11R)-4-methyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-12,13-dione —— C13H16O4
(1S,2S,4R,11R)-4-methyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-ene-12,13-dione
—— (1R,2R,4R,6R,8S,11S)-8-hydroxy-4,9-dimethyl-15-methylidene-2-(2-methylpropanoyl)-5,13-dioxatricyclo[9.4.0.04,6]pentadec-9-en-12-one —— C20H28O5
(1R,2R,4R,6R,8S,11S)-8-hydroxy-4,9-dimethyl-15-methylidene-2-(2-methylpropanoyl)-5,13-dioxatricyclo[9.4.0.04,6]pentadec-9-en-12-one
—— 3,4-Di(propan-2-ylidene)oxolan-2-one —— C10H14O2
3,4-Di(propan-2-ylidene)oxolan-2-one
—— (8-Ethyl-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl) 2,2-dimethylbutanoate —— C15H24O4
(8-Ethyl-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl) 2,2-dimethylbutanoate
—— 3-Chloro-6,6-diethyloxane-2,4-dione —— C9H13ClO3
3-Chloro-6,6-diethyloxane-2,4-dione
—— 5,5,9-Trimethyl-3-oxabicyclo[4.3.1]decan-2-one —— C12H20O2
5,5,9-Trimethyl-3-oxabicyclo[4.3.1]decan-2-one
—— 4-Hydroxy-5-(1-hydroxypropan-2-yl)oxolane-2,3-dione —— C7H10O5
4-Hydroxy-5-(1-hydroxypropan-2-yl)oxolane-2,3-dione
—— 6-Propyl-2-oxabicyclo[2.2.2]octan-3-one —— C10H16O2
6-Propyl-2-oxabicyclo[2.2.2]octan-3-one
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-(2-hydroxypropylperoxy)oxolane-2,3-dione —— C9H14O8
(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-(2-hydroxypropylperoxy)oxolane-2,3-dione
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-3-(2-ethylhexoxy)oxolane-2,4-dione —— C14H24O6
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3-(2-ethylhexoxy)oxolane-2,4-dione
—— 5-Bromo-6-(4-bromo-phenyl)-5-ethyl-3,3-dimethyl-dihydro-pyran-2,4-dione —— C15H16Br2O3
5-Bromo-6-(4-bromo-phenyl)-5-ethyl-3,3-dimethyl-dihydro-pyran-2,4-dione
—— [(1S,3R,7S,8S,8aR)-8-[2-[(3S,4R,6R)-6-hydroxy-3-methyl-2-oxooxan-4-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C26H40O5
[(1S,3R,7S,8S,8aR)-8-[2-[(3S,4R,6R)-6-hydroxy-3-methyl-2-oxooxan-4-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— (2-Oxooxolan-3-yl)methyl formate —— C6H8O4
(2-Oxooxolan-3-yl)methyl formate
—— N-[2-(3-fluorophenyl)cyclopropyl]-4-methyl-3-oxo-7-propan-2-yl-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C20H24FNO3
N-[2-(3-fluorophenyl)cyclopropyl]-4-methyl-3-oxo-7-propan-2-yl-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— 4-Hydroxy-5-(1-hydroxypropyl)-3-methyloxolan-2-one —— C8H14O4
4-Hydroxy-5-(1-hydroxypropyl)-3-methyloxolan-2-one
—— 2-Methylpropane;oxolan-2-one —— C8H16O2
2-Methylpropane;oxolan-2-one
—— 4-Hydroxy-5-(methoxymethyl)oxane-2,3-dione —— C7H10O5
4-Hydroxy-5-(methoxymethyl)oxane-2,3-dione
—— 2,3-Difluorobutane;3,8-dimethyl-2-oxaspiro[4.5]decan-1-one;2-methylpropane;2-methylpropanenitrile —— C23H43F2NO2
2,3-Difluorobutane;3,8-dimethyl-2-oxaspiro[4.5]decan-1-one;2-methylpropane;2-methylpropanenitrile
—— (5-Oxo-4-oxatricyclo[4.3.1.13,8]undecan-6-yl) 2-tert-butyl-2,4,4-trimethylpentanoate —— C22H36O4
(5-Oxo-4-oxatricyclo[4.3.1.13,8]undecan-6-yl) 2-tert-butyl-2,4,4-trimethylpentanoate
—— Ethyl 3-butylsulfanyl-2-(butylsulfanylmethyl)-4,5-dioxooxolane-2-carboxylate —— C16H26O5S2
Ethyl 3-butylsulfanyl-2-(butylsulfanylmethyl)-4,5-dioxooxolane-2-carboxylate
—— 5-Azidooxepan-2-one —— C6H9N3O2
5-Azidooxepan-2-one