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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-Ethyl-2-adamantyl) 2,2-dimethylbutanoate;(7-oxo-6-oxabicyclo[3.2.1]octan-4-yl) 2,2-dimethylbutanoate —— C31H50O6
(2-Ethyl-2-adamantyl) 2,2-dimethylbutanoate;(7-oxo-6-oxabicyclo[3.2.1]octan-4-yl) 2,2-dimethylbutanoate
—— 3,8-Dimethyl-2-oxaspiro[4.5]decan-1-one;3,8-dimethyl-7-oxaspiro[4.5]decan-6-one —— C22H36O4
3,8-Dimethyl-2-oxaspiro[4.5]decan-1-one;3,8-dimethyl-7-oxaspiro[4.5]decan-6-one
—— 2-(5-Oxooxolan-3-yl)propan-2-yl 4-(2,5-dihydroxy-3,4-dimethylpyrrol-1-yl)cyclohexane-1-carboxylate —— C20H29NO6
2-(5-Oxooxolan-3-yl)propan-2-yl 4-(2,5-dihydroxy-3,4-dimethylpyrrol-1-yl)cyclohexane-1-carboxylate
—— 1,4,5,5-Tetramethyl-2-oxabicyclo<2.2.1>heptan-3-on 55790-86-8 C10H16O2
1,4,5,5-Tetramethyl-2-oxabicyclo<2.2.1>heptan-3-on
—— 6-[2-(Oxiran-2-yl)ethyl]oxan-2-one —— C9H14O3
6-[2-(Oxiran-2-yl)ethyl]oxan-2-one
—— (2-Oxooxan-3-yl)methyl 2-methylprop-2-enoate —— C10H14O4
(2-Oxooxan-3-yl)methyl 2-methylprop-2-enoate
—— 3,5-Dichloro-4-phenyliminooxolan-2-one —— C10H7Cl2NO2
3,5-Dichloro-4-phenyliminooxolan-2-one
—— [(3R)-3-benzyl-5-oxooxolan-3-yl]carbamic acid —— C12H13NO4
[(3R)-3-benzyl-5-oxooxolan-3-yl]carbamic acid
—— (5R)-4-hydroxy-5-methyloxolane-2,3-dione —— C5H6O4
(5R)-4-hydroxy-5-methyloxolane-2,3-dione
—— 5-(2-Phenylethyl)oxolane-2,4-dione —— C12H12O3
5-(2-Phenylethyl)oxolane-2,4-dione
—— (5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,4-dione —— C12H22O6Si
(5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,4-dione
—— 4,6-Dihydroxyoxane-2,3-dione —— C5H6O5
4,6-Dihydroxyoxane-2,3-dione
—— [(3R)-4-[[(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]oxy]-3-methyl-4-oxobutyl]boronic acid —— C24H37BO7
[(3R)-4-[[(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]oxy]-3-methyl-4-oxobutyl]boronic acid
—— 3,3-Diethoxyoxepan-2-one —— C10H18O4
3,3-Diethoxyoxepan-2-one
—— 4,5,5-Trimethyloxolane-2,3-dione —— C7H10O3
4,5,5-Trimethyloxolane-2,3-dione
—— 5-Carbamoyl-5-hydroxy-2-oxooxolane-3-carboxylic acid —— C6H7NO6
5-Carbamoyl-5-hydroxy-2-oxooxolane-3-carboxylic acid
—— 6,6-Dimethyl-3-(2-thiophen-2-ylacetyl)oxane-2,4-dione —— C13H14O4S
6,6-Dimethyl-3-(2-thiophen-2-ylacetyl)oxane-2,4-dione
—— (2S)-3-[(2S,3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]-2-methylpropanal —— C17H32O4Si
(2S)-3-[(2S,3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]-2-methylpropanal
—— 2-[2-(2,12-Dimethyl-7-oxotridecan-2-yl)-4-hydroxy-6-oxooxan-4-yl]acetic acid —— C22H38O6
2-[2-(2,12-Dimethyl-7-oxotridecan-2-yl)-4-hydroxy-6-oxooxan-4-yl]acetic acid
—— 5-(Cyclohexylmethyl)oxolane-2,4-dione —— C11H16O3
5-(Cyclohexylmethyl)oxolane-2,4-dione
—— 4-Chloro-2-oxa-6-azabicyclo[3.1.0]hex-5-en-3-one —— C4H2ClNO2
4-Chloro-2-oxa-6-azabicyclo[3.1.0]hex-5-en-3-one
—— (5R)-3-butoxy-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,4-dione —— C10H16O6
(5R)-3-butoxy-5-[(1S)-1,2-dihydroxyethyl]oxolane-2,4-dione
—— (7-Oxo-6-oxabicyclo[3.2.1]octan-4-yl) 2-methylbutanoate;(5-oxooxolan-2-yl) 2-methylbutanoate —— C21H32O8
(7-Oxo-6-oxabicyclo[3.2.1]octan-4-yl) 2-methylbutanoate;(5-oxooxolan-2-yl) 2-methylbutanoate
—— 3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-one;triethyl(methyl)azanium —— C12H25FNO4+
3-Fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-one;triethyl(methyl)azanium
—— (1R,4S,5R,10S,17S)-4,17-dimethylspiro[18-oxapentacyclo[8.7.2.01,9.04,8.012,17]nonadec-11-ene-5,5'-oxolane]-2',14,19-trione —— C23H28O5
(1R,4S,5R,10S,17S)-4,17-dimethylspiro[18-oxapentacyclo[8.7.2.01,9.04,8.012,17]nonadec-11-ene-5,5'-oxolane]-2',14,19-trione
—— 2-[6-(5-Oxooxolan-2-yl)hexyl]decanal —— C20H36O3
2-[6-(5-Oxooxolan-2-yl)hexyl]decanal
—— 3-Ethyl-4-tridecyloxetan-2-one —— C18H34O2
3-Ethyl-4-tridecyloxetan-2-one
—— Ethane;2-oxabicyclo[2.2.1]heptan-3-one —— C10H20O2
Ethane;2-oxabicyclo[2.2.1]heptan-3-one
—— [(6S)-1-[[(2S,3S,4S)-3,7-dihydroxy-8-[(2S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-2,4-dimethyloct-5-enyl]-methylamino]-3-hydroxy-2,4,6-trimethyl-1-oxodeca-7,9-dien-5-yl] carbamate —— C32H54N2O9
[(6S)-1-[[(2S,3S,4S)-3,7-dihydroxy-8-[(2S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-2,4-dimethyloct-5-enyl]-methylamino]-3-hydroxy-2,4,6-trimethyl-1-oxodeca-7,9-dien-5-yl] carbamate
—— (5S)-5-methyl-5-phenyloxolane-2,4-dione —— C11H10O3
(5S)-5-methyl-5-phenyloxolane-2,4-dione
—— [Hydroxy(phenyl)methyl](5-oxotetrahydrofuran-3-yl)phosphinate —— C11H12O5P-
[Hydroxy(phenyl)methyl](5-oxotetrahydrofuran-3-yl)phosphinate
—— [Hydroxy(phenyl)methyl]-(5-oxooxolan-3-yl)phosphinic acid —— C11H13O5P
[Hydroxy(phenyl)methyl]-(5-oxooxolan-3-yl)phosphinic acid
—— 3-(2,4,6-Trimethylphenyl)-1-oxaspiro[4.4]nonane-2,4-dione —— C17H20O3
3-(2,4,6-Trimethylphenyl)-1-oxaspiro[4.4]nonane-2,4-dione
—— (1,8-Dimethyl-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-6-yl) 2-tert-butyl-2,4,4-trimethylhexanoate —— C25H42O4
(1,8-Dimethyl-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-6-yl) 2-tert-butyl-2,4,4-trimethylhexanoate
—— 2-Ethyl-2-methyl-5-oxatricyclo[5.2.1.04,8]decan-6-one —— C12H18O2
2-Ethyl-2-methyl-5-oxatricyclo[5.2.1.04,8]decan-6-one
—— (3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-prop-1-enyloxan-2-one —— C10H16O3
(3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-prop-1-enyloxan-2-one
—— 4-Hydroxy-3-[(4-methoxy-3-methylbut-2-enoxy)methylidene]-8,8-dimethyl-3a,4,5,6,7,8b-hexahydroindeno[1,2-b]furan-2-one —— C20H28O5
4-Hydroxy-3-[(4-methoxy-3-methylbut-2-enoxy)methylidene]-8,8-dimethyl-3a,4,5,6,7,8b-hexahydroindeno[1,2-b]furan-2-one
—— 7-Chloro-2-oxooctahydro-3,6-methano-1-benzofuran-8-carboxylic acid —— C10H11ClO4
7-Chloro-2-oxooctahydro-3,6-methano-1-benzofuran-8-carboxylic acid
—— (4S,5S)-5-[(2R)-2-[(1R,3aR,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one —— C21H31BrO2
(4S,5S)-5-[(2R)-2-[(1R,3aR,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one
—— 5-Tert-butyl-4-hydroxyoxolane-2,3-dione —— C8H12O4
5-Tert-butyl-4-hydroxyoxolane-2,3-dione
—— (5R)-5-[(2R)-2-[(1R,3aR,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4,4-dimethyl-3-methylideneoxolan-2-one —— C21H31BrO2
(5R)-5-[(2R)-2-[(1R,3aR,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4,4-dimethyl-3-methylideneoxolan-2-one
—— 4-(3-Ethylheptoxy)-8,8-dimethyl-3-oxabicyclo[5.1.0]octane-2,6-dione —— C18H30O4
4-(3-Ethylheptoxy)-8,8-dimethyl-3-oxabicyclo[5.1.0]octane-2,6-dione
—— 3,3a,4,5,7,8,9a,9b-Octahydroazuleno[8,7-b]furan-2,9-dione —— C12H14O3
3,3a,4,5,7,8,9a,9b-Octahydroazuleno[8,7-b]furan-2,9-dione
—— 1,3a,4,5,6,6a-Hexahydrocyclopenta[c]furan-3-one;propane —— C10H18O2
1,3a,4,5,6,6a-Hexahydrocyclopenta[c]furan-3-one;propane
—— 2-(2-methyl-5-oxotetrahydrofuran-3-yl)acetic acid 27203-31-2 C7H10O4
2-(2-methyl-5-oxotetrahydrofuran-3-yl)acetic acid
—— (1R,5S)-6,6-dimethyl-4-propan-2-yl-3-oxabicyclo[3.1.0]hexan-2-one;(3S)-2,2-dimethyl-3-[(E)-prop-1-enyl]cyclopropane-1-carboxylic acid —— C19H30O4
(1R,5S)-6,6-dimethyl-4-propan-2-yl-3-oxabicyclo[3.1.0]hexan-2-one;(3S)-2,2-dimethyl-3-[(E)-prop-1-enyl]cyclopropane-1-carboxylic acid
—— 3-[3-(Dimethylamino)prop-2-enoyl]-6-methyloxane-2,4-dione —— C11H15NO4
3-[3-(Dimethylamino)prop-2-enoyl]-6-methyloxane-2,4-dione
—— 5-Ethyl-3-methyl-4-prop-1-enyloxolan-2-one —— C10H16O2
5-Ethyl-3-methyl-4-prop-1-enyloxolan-2-one
—— 4,4-Dibromo-5-hydroxyoxolan-2-one —— C4H4Br2O3
4,4-Dibromo-5-hydroxyoxolan-2-one
—— 5-Amino-4-hydroxy-5-methyloxolane-2,3-dione —— C5H7NO4
5-Amino-4-hydroxy-5-methyloxolane-2,3-dione