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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
—— 5-Methyl-5-phenyl-3-(trifluoromethyl)oxolan-2-one —— C12H11F3O2
5-Methyl-5-phenyl-3-(trifluoromethyl)oxolan-2-one
—— Butadienolid —— C4H2O2
Butadienolid
—— 2-(3-Hydroxy-2,4,6-trioxooxan-3-yl)acetaldehyde —— C7H6O6
2-(3-Hydroxy-2,4,6-trioxooxan-3-yl)acetaldehyde
—— 8-(Iodomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione —— C10H13IO3
8-(Iodomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
—— (2<sup>1</sup>-bromo-<i>dl</i>-camphoric acid )-anhydride —— C10H13BrO3
(2<sup>1</sup>-bromo-<i>dl</i>-camphoric acid )-anhydride
—— Ethane;3-methylideneoxolan-2-one —— C7H12O2
Ethane;3-methylideneoxolan-2-one
—— 3,3-Dipropoxyoxepan-2-one —— C12H22O4
3,3-Dipropoxyoxepan-2-one
—— 3,3a,4,5,6,6a,9a,9b-Octahydroazuleno[8,7-b]furan-2,9-dione —— C12H14O3
3,3a,4,5,6,6a,9a,9b-Octahydroazuleno[8,7-b]furan-2,9-dione
—— (1S,2R,4S,11S)-8-methyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one —— C14H18O3
(1S,2R,4S,11S)-8-methyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
—— 4,4,5,5-Tetrahydroxyoxolan-2-one —— C4H6O6
4,4,5,5-Tetrahydroxyoxolan-2-one
—— 3-Hydroxy-5-[1-hydroxy-2-(2-oxobutoxy)ethyl]oxolane-2,4-dione —— C10H14O7
3-Hydroxy-5-[1-hydroxy-2-(2-oxobutoxy)ethyl]oxolane-2,4-dione
—— (6R)-6-but-1-enyl-5-but-2-enyl-4-hydroxyoxan-2-one —— C13H20O3
(6R)-6-but-1-enyl-5-but-2-enyl-4-hydroxyoxan-2-one
—— (3R,5S)-3-(3-methylbutyl)-5-(2-phenylethyl)oxolan-2-one —— C17H24O2
(3R,5S)-3-(3-methylbutyl)-5-(2-phenylethyl)oxolan-2-one
—— 5-(2-Methylpropyl)oxolane-2,4-dione —— C8H12O3
5-(2-Methylpropyl)oxolane-2,4-dione
—— [3-(2-Oxooxepane-3-carbonyl)oxy-2,2-bis[(2-oxooxepane-3-carbonyl)oxymethyl]propyl] 2-oxooxepane-3-carboxylate —— C33H44O16
[3-(2-Oxooxepane-3-carbonyl)oxy-2,2-bis[(2-oxooxepane-3-carbonyl)oxymethyl]propyl] 2-oxooxepane-3-carboxylate
—— [(2R)-2-hydroxy-3-[(2R)-4-hydroxy-3,5-dioxooxolan-2-yl]propyl] [(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] carbonate —— C14H20O13
[(2R)-2-hydroxy-3-[(2R)-4-hydroxy-3,5-dioxooxolan-2-yl]propyl] [(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] carbonate
—— 6-Phenyloxane-2,3-dione —— C11H10O3
6-Phenyloxane-2,3-dione
—— [6-(Hydroxymethyl)-5-oxo-4-oxatetracyclo[4.3.1.01,8.03,10]decan-2-yl] pentanoate —— C15H20O5
[6-(Hydroxymethyl)-5-oxo-4-oxatetracyclo[4.3.1.01,8.03,10]decan-2-yl] pentanoate
—— (1S)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid —— C12H10O4
(1S)-2-oxo-6-phenyl-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid
—— (6S)-3,6-bis(sulfanyl)oxan-2-one —— C5H8O2S2
(6S)-3,6-bis(sulfanyl)oxan-2-one
—— (3E)-8,8-dimethyl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-3a,4,4a,5,6,7,8a,8b-octahydroindeno[1,2-b]furan-2-one;propane —— C22H32O5
(3E)-8,8-dimethyl-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylidene]-3a,4,4a,5,6,7,8a,8b-octahydroindeno[1,2-b]furan-2-one;propane
—— (3aS,5S,6aR)-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one —— C7H10O3
(3aS,5S,6aR)-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— 7,9-Dimethyl-2-oxaspiro[4.4]nonan-1-one —— C10H16O2
7,9-Dimethyl-2-oxaspiro[4.4]nonan-1-one
—— 5-(2-Methylpropyl)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-3-one —— C11H18O2
5-(2-Methylpropyl)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-3-one
—— Ethane;2-methylhex-1-ene;oxolan-2-one —— C13H26O2
Ethane;2-methylhex-1-ene;oxolan-2-one
—— (4R)-4-phenyl-3-[(3S)-3-phenylbutanoyl]oxolan-2-one —— C20H20O3
(4R)-4-phenyl-3-[(3S)-3-phenylbutanoyl]oxolan-2-one
—— 5-[2-(Furan-2-yl)-1,3-dioxolan-4-yl]-3-hydroxyoxolane-2,4-dione —— C11H10O7
5-[2-(Furan-2-yl)-1,3-dioxolan-4-yl]-3-hydroxyoxolane-2,4-dione
—— (5R)-5-[(1R)-1,2-dihydroxyethyl]-4-(2-hydroxy-3-methylpentoxy)oxolane-2,3-dione —— C12H20O7
(5R)-5-[(1R)-1,2-dihydroxyethyl]-4-(2-hydroxy-3-methylpentoxy)oxolane-2,3-dione
—— 5-[12-(2,3-Dihydrofuran-5-yl)-7-oxo-2,12-diphenyltridecan-2-yl]oxolan-2-one —— C33H42O4
5-[12-(2,3-Dihydrofuran-5-yl)-7-oxo-2,12-diphenyltridecan-2-yl]oxolan-2-one
—— [(1S,3S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-3-prop-1-enyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C27H40O5
[(1S,3S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-3-prop-1-enyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— 4,4,5-Trimethyl-2-oxooxane-3-carboxylic acid —— C9H14O4
4,4,5-Trimethyl-2-oxooxane-3-carboxylic acid
—— (4R,5S)-4-hydroxy-5-[(propan-2-ylamino)methyl]oxolan-2-one —— C8H15NO3
(4R,5S)-4-hydroxy-5-[(propan-2-ylamino)methyl]oxolan-2-one
—— (5R)-5-tert-butyl-3-prop-2-enyloxolane-2,4-dione —— C11H16O3
(5R)-5-tert-butyl-3-prop-2-enyloxolane-2,4-dione
—— 3-Chloro-6-[2-(cyclohexen-1-yl)ethyl]-6-cyclopentyloxane-2,4-dione —— C18H25ClO3
3-Chloro-6-[2-(cyclohexen-1-yl)ethyl]-6-cyclopentyloxane-2,4-dione
—— (3S,4S)-4-hex-5-enyl-3-hexyloxetan-2-one —— C15H26O2
(3S,4S)-4-hex-5-enyl-3-hexyloxetan-2-one
—— Ethane;(8-methoxy-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-1-yl) 2,2-dimethylpropanoate —— C18H30O5
Ethane;(8-methoxy-5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-1-yl) 2,2-dimethylpropanoate
—— 3-Chloro-6-cyclopentyl-6-[2-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]ethyl]oxane-2,4-dione —— C23H26ClNO4
3-Chloro-6-cyclopentyl-6-[2-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]ethyl]oxane-2,4-dione
—— (3R,5S)-5-[(1R)-1,2-bis(trimethylsilyloxy)ethyl]-3-trimethylsilyloxyoxolan-2-one —— C15H34O5Si3
(3R,5S)-5-[(1R)-1,2-bis(trimethylsilyloxy)ethyl]-3-trimethylsilyloxyoxolan-2-one
—— 5,5-Di(henpentacontoxy)-4-methylpentan-2-one;5-henpentacontoxy-4-methyloxolan-2-one —— C164H326O6
5,5-Di(henpentacontoxy)-4-methylpentan-2-one;5-henpentacontoxy-4-methyloxolan-2-one
—— 6-methoxy-5,6-dimethyloxan-2-one;methyl 5,5-dimethoxy-4-methylhexanoate;methyl (E)-5-methoxy-4-methylpent-4-enoate —— C26H48O10
6-methoxy-5,6-dimethyloxan-2-one;methyl 5,5-dimethoxy-4-methylhexanoate;methyl (E)-5-methoxy-4-methylpent-4-enoate
—— 2-Ethoxy-5-oxooxolane-3-carboxamide —— C7H11NO4
2-Ethoxy-5-oxooxolane-3-carboxamide
—— methyl (2'R,9'S,15'S)-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tricyclo[8.7.0.02,7]heptadec-7-ene]-9'-carboxylate —— C24H34O5
methyl (2'R,9'S,15'S)-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tricyclo[8.7.0.02,7]heptadec-7-ene]-9'-carboxylate
—— 7-(4-Methylpentyl)-3-oxatricyclo[3.2.1.11,5]nonan-2-one —— C14H22O2
7-(4-Methylpentyl)-3-oxatricyclo[3.2.1.11,5]nonan-2-one
—— (4R,6R)-4-methoxy-6-[(6R)-6-methoxy-3-methyl-1-tri(propan-2-yl)silyloxynona-2,4-dienyl]oxan-2-one —— C26H48O5Si
(4R,6R)-4-methoxy-6-[(6R)-6-methoxy-3-methyl-1-tri(propan-2-yl)silyloxynona-2,4-dienyl]oxan-2-one
—— (5R)-5-[(1S)-1,2-dihydroxyethyl]-3-ethoxyoxolane-2,4-dione —— C8H12O6
(5R)-5-[(1S)-1,2-dihydroxyethyl]-3-ethoxyoxolane-2,4-dione
—— 4,7,7-Trimethyl-1-(thiomorpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one —— C14H21NO3S
4,7,7-Trimethyl-1-(thiomorpholine-4-carbonyl)-2-oxabicyclo[2.2.1]heptan-3-one
—— 6-Ethyl-3,5-diethynyl-4-methyloxan-2-one —— C12H14O2
6-Ethyl-3,5-diethynyl-4-methyloxan-2-one
—— 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
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
—— (10R,14S,15S,18S)-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
(10R,14S,15S,18S)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-4-ene-15,5'-oxolane]-2',7-dione
—— Ethane;5-methyloxolan-2-one —— C7H14O2
Ethane;5-methyloxolan-2-one