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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
—— alpha-Bromo-alpha-trifluoroacetyl-delta-valerolactone, hydrate —— C7H8BrF3O4
alpha-Bromo-alpha-trifluoroacetyl-delta-valerolactone, hydrate
—— (5R)-5-(1,2-dihydroxyethyl)-3-octadecoxyoxolane-2,4-dione —— C24H44O6
(5R)-5-(1,2-dihydroxyethyl)-3-octadecoxyoxolane-2,4-dione
—— Tetramic acid, 74 —— C18H16O3S
Tetramic acid, 74
—— 4-(3,6-Dihydro-4-hydroxy-6-oxo-2-phenyl-5-[(phenylethyl)thio]-2H-pyran-2-yl)butyramide —— C23H25NO4S
4-(3,6-Dihydro-4-hydroxy-6-oxo-2-phenyl-5-[(phenylethyl)thio]-2H-pyran-2-yl)butyramide
—— 4-hydroxy-6-(4-methylpentyl)-6-phenyl-3-[(2-phenylethyl)sulfanyl]-5,6-dihydro-2H-pyran-2-one —— C25H30O3S
4-hydroxy-6-(4-methylpentyl)-6-phenyl-3-[(2-phenylethyl)sulfanyl]-5,6-dihydro-2H-pyran-2-one
—— 6-Butyl-5,6-dihydro-4-hydroxy-6-phenyl-3-[(2-phenylethyl)thio]-2H-pyran-2-one —— C23H26O3S
6-Butyl-5,6-dihydro-4-hydroxy-6-phenyl-3-[(2-phenylethyl)thio]-2H-pyran-2-one
—— 3-(benzylsulfanyl)-4-hydroxy-6-phenyl-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one —— C26H24O3S
3-(benzylsulfanyl)-4-hydroxy-6-phenyl-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
—— 3-(benzylsulfanyl)-6-hexyl-4-hydroxy-6-phenyl-5,6-dihydro-2H-pyran-2-one —— C24H28O3S
3-(benzylsulfanyl)-6-hexyl-4-hydroxy-6-phenyl-5,6-dihydro-2H-pyran-2-one
—— 1-O-Deacetylkhayanolide E —— C27H32O10
1-O-Deacetylkhayanolide E
—— (1S,10S)-4,13,13-trimethyl-9-methylidene-5,11-dioxatricyclo[8.3.0.04,6]tridecan-12-one —— C15H22O3
(1S,10S)-4,13,13-trimethyl-9-methylidene-5,11-dioxatricyclo[8.3.0.04,6]tridecan-12-one
—— [(2R,3S,5R,6R,7R,8R)-2-hydroxy-7-methyl-11-oxo-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-8-yl] acetate —— C17H20O7
[(2R,3S,5R,6R,7R,8R)-2-hydroxy-7-methyl-11-oxo-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-8-yl] acetate
—— [1-[2-Oxo-5-(pentoxymethyl)oxolan-3-yl]propan-2-ylideneamino]thiourea —— C14H25N3O3S
[1-[2-Oxo-5-(pentoxymethyl)oxolan-3-yl]propan-2-ylideneamino]thiourea
—— 4-Isothiocyanatooxolan-2-one —— C5H5NO2S
4-Isothiocyanatooxolan-2-one
—— azanium;(4R)-2-[2-[(1R,2R,6S,8S,8aS)-2,6-dimethyl-8-[(2R)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-6-oxooxan-4-olate —— C24H39NO5
azanium;(4R)-2-[2-[(1R,2R,6S,8S,8aS)-2,6-dimethyl-8-[(2R)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-6-oxooxan-4-olate
—— (2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]propanal —— C22H44O5Si2
(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]propanal
—— (2'S,5'R,16'S)-5'-[tert-butyl(dimethyl)silyl]oxy-2',16'-dimethylspiro[1,3-dioxolane-2,15'-10-oxatetracyclo[9.7.0.02,7.012,16]octadecane]-9'-one —— C27H46O5Si
(2'S,5'R,16'S)-5'-[tert-butyl(dimethyl)silyl]oxy-2',16'-dimethylspiro[1,3-dioxolane-2,15'-10-oxatetracyclo[9.7.0.02,7.012,16]octadecane]-9'-one
—— 9,9-Dimethyl-8-phenyl-7-oxaspiro[4.5]decane-6,10-dione —— C17H20O3
9,9-Dimethyl-8-phenyl-7-oxaspiro[4.5]decane-6,10-dione
—— [(1S,3S,7S,8S)-3-[tert-butyl(dimethyl)silyl]oxy-8-[2-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2-diethoxyphosphorylpropanoate —— C37H67O9PSi2
[(1S,3S,7S,8S)-3-[tert-butyl(dimethyl)silyl]oxy-8-[2-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2-diethoxyphosphorylpropanoate
—— [(7S,8S,8aR)-8-[2-[(4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-7-methyl-3-(trideuteriomethyl)-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate —— C30H50O5Si
[(7S,8S,8aR)-8-[2-[(4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-7-methyl-3-(trideuteriomethyl)-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
—— [(1R,3S,7S,8S)-8-[2-[(2S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate —— C31H52O5Si
[(1R,3S,7S,8S)-8-[2-[(2S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
—— [(1S,3S,7S,8S,8aR)-3-[tert-butyl(dimethyl)silyl]oxy-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-diethoxyphosphorylbutanoate —— C32H55O9PSi
[(1S,3S,7S,8S,8aR)-3-[tert-butyl(dimethyl)silyl]oxy-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-diethoxyphosphorylbutanoate
—— (4R,6R)-6-[2-[(1S,2S,6S,8S,8aR)-6-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-hydroxyoxan-2-one —— C24H40O5Si
(4R,6R)-6-[2-[(1S,2S,6S,8S,8aR)-6-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-hydroxyoxan-2-one
—— (3aS,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-3a-methyl-4,6a-dihydro-1H-cyclopenta[c]furan-3-one —— C15H26O4Si
(3aS,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-3a-methyl-4,6a-dihydro-1H-cyclopenta[c]furan-3-one
—— ethyl 2-[(3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-6-methylidene-3-oxo-4,5-dihydro-1H-cyclopenta[c]furan-5-yl]acetate —— C20H34O5Si
ethyl 2-[(3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-6-methylidene-3-oxo-4,5-dihydro-1H-cyclopenta[c]furan-5-yl]acetate
—— [(3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-6-methylidene-3-oxo-4,5-dihydro-1H-cyclopenta[c]furan-5-yl]methyl propanoate —— C20H34O5Si
[(3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-6-methylidene-3-oxo-4,5-dihydro-1H-cyclopenta[c]furan-5-yl]methyl propanoate
—— (3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-3-oxo-1,4-dihydrocyclopenta[c]furan-6-carbaldehyde —— C16H26O4Si
(3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-3-oxo-1,4-dihydrocyclopenta[c]furan-6-carbaldehyde
—— (3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-3a,6a-dimethyl-1,4-dihydrocyclopenta[c]furan-3-one —— C16H28O4Si
(3aS,4S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-3a,6a-dimethyl-1,4-dihydrocyclopenta[c]furan-3-one
—— (1S,2S,7S,8S)-2-(3-bromobut-3-enyl)-7-[tert-butyl(dimethyl)silyl]oxy-1,8-dimethyl-3,10-dioxatricyclo[6.3.0.02,6]undec-5-ene-4,9-dione —— C21H31BrO5Si
(1S,2S,7S,8S)-2-(3-bromobut-3-enyl)-7-[tert-butyl(dimethyl)silyl]oxy-1,8-dimethyl-3,10-dioxatricyclo[6.3.0.02,6]undec-5-ene-4,9-dione
—— 14-Hydroxy-2,3,13,13-tetramethyl-7,10,12-trioxatetracyclo[9.2.1.02,8.06,8]tetradecan-9-one —— C15H22O5
14-Hydroxy-2,3,13,13-tetramethyl-7,10,12-trioxatetracyclo[9.2.1.02,8.06,8]tetradecan-9-one
—— (1S,2R,6R,7S,8S)-2-but-3-enyl-7-[tert-butyl(dimethyl)silyl]oxy-1,8-dimethyl-3,10-dioxatricyclo[6.3.0.02,6]undecane-4,9-dione —— C21H34O5Si
(1S,2R,6R,7S,8S)-2-but-3-enyl-7-[tert-butyl(dimethyl)silyl]oxy-1,8-dimethyl-3,10-dioxatricyclo[6.3.0.02,6]undecane-4,9-dione
—— (2S,5R)-2-[tert-butyl(dimethyl)silyl]oxy-6-oxabicyclo[3.2.0]heptan-7-one —— C12H22O3Si
(2S,5R)-2-[tert-butyl(dimethyl)silyl]oxy-6-oxabicyclo[3.2.0]heptan-7-one
—— methyl 2-[(3aS,4S,5S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-6-methylidene-3-oxo-4,5-dihydro-1H-cyclopenta[c]furan-5-yl]acetate —— C19H32O5Si
methyl 2-[(3aS,4S,5S,6aS)-4-[tert-butyl(dimethyl)silyl]oxy-3a,6a-dimethyl-6-methylidene-3-oxo-4,5-dihydro-1H-cyclopenta[c]furan-5-yl]acetate
—— Dibutyl-[4-[2-oxo-5-(propoxymethyl)oxolan-3-yl]but-2-ynyl]azanium —— C20H36NO3+
Dibutyl-[4-[2-oxo-5-(propoxymethyl)oxolan-3-yl]but-2-ynyl]azanium
—— 3,6,9-Trioxatetracyclo[6.2.1.02,4.05,7]undecan-10-one —— C8H8O4
3,6,9-Trioxatetracyclo[6.2.1.02,4.05,7]undecan-10-one
—— alpha-Methylene-gamma-butyrolactone 3 —— C8H10O5
alpha-Methylene-gamma-butyrolactone 3
—— (4R)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one;(4S)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one —— C12H14Cl6O4
(4R)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one;(4S)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one
—— (4R)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one —— C6H7Cl3O2
(4R)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one
—— (4S)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one —— C6H7Cl3O2
(4S)-3,3-dimethyl-4-(trichloromethyl)oxetan-2-one
—— D-galactaro-1,4-lactone(1-) —— C6H7O7-
D-galactaro-1,4-lactone(1-)
—— 3-[2-(5-Mercapto-4H-[1,2,4]triazol-3-yl)-ethyl]-5-propoxymethyl-dihydro-furan-2-one —— C12H19N3O3S
3-[2-(5-Mercapto-4H-[1,2,4]triazol-3-yl)-ethyl]-5-propoxymethyl-dihydro-furan-2-one
—— anditomin 79874-93-4 C25H30O5
anditomin
—— andilesin D —— C25H30O6
andilesin D
—— (3S,4S,5R)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]oxolan-2-one —— C6H10O5
(3S,4S,5R)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]oxolan-2-one
—— (4-Ethyl-5-oxotetrahydrofuran-2-yl)methyl carbamimidothioate (non-preferred name) —— C8H14N2O2S
(4-Ethyl-5-oxotetrahydrofuran-2-yl)methyl carbamimidothioate (non-preferred name)
—— (3R,5R)-5-[(2R)-2-[tert-butyl(dimethyl)silyl]oxypropyl]-3-(2-methylpropyl)oxolan-2-one —— C17H34O3Si
(3R,5R)-5-[(2R)-2-[tert-butyl(dimethyl)silyl]oxypropyl]-3-(2-methylpropyl)oxolan-2-one
—— 5,5-dimethyl-3-[2-(5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)propyl]dihydrofuran-2(3H)-one —— C11H17N3O2S
5,5-dimethyl-3-[2-(5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)propyl]dihydrofuran-2(3H)-one
—— 5-(2-Phenylmethoxyimino-1-trimethylsilyloxyethyl)-3,4-bis(trimethylsilyloxy)oxolan-2-one —— C22H39NO6Si3
5-(2-Phenylmethoxyimino-1-trimethylsilyloxyethyl)-3,4-bis(trimethylsilyloxy)oxolan-2-one
—— cis-beta-Methyloctalactone —— C9H16O2
cis-beta-Methyloctalactone
—— GA4, MO-Tms —— C26H42O5Si2
GA4, MO-Tms
—— Arabinonic acid, gamma-lactone, tris-TMS —— C14H32O5Si3
Arabinonic acid, gamma-lactone, tris-TMS