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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
—— (8-Hydroperoxy-5,13-dimethyl-9,18-dimethylidene-17-oxo-4,16-dioxatricyclo[13.3.0.03,5]octadec-12-en-14-yl) acetate —— C22H30O7
(8-Hydroperoxy-5,13-dimethyl-9,18-dimethylidene-17-oxo-4,16-dioxatricyclo[13.3.0.03,5]octadec-12-en-14-yl) acetate
—— 5'-(Furan-3-yl)-6-hydroxy-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-8(12)-ene-9,3'-oxolane]-2',3-dione —— C19H20O6
5'-(Furan-3-yl)-6-hydroxy-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-8(12)-ene-9,3'-oxolane]-2',3-dione
—— 10-hydroxy-9,11,12-trimethyl-12-[2-(5-oxo-2H-furan-3-yl)ethyl]-2-oxatricyclo[6.2.2.04,9]dodec-4-en-3-one —— C20H26O5
10-hydroxy-9,11,12-trimethyl-12-[2-(5-oxo-2H-furan-3-yl)ethyl]-2-oxatricyclo[6.2.2.04,9]dodec-4-en-3-one
—— 3-(Cyclohexylmethyl)-5-[(4-fluorophenyl)methyl]-11-hydroxy-4-sulfanylidene-8-oxa-3,5-diazatricyclo[5.2.2.02,6]undecan-9-one —— C22H27FN2O3S
3-(Cyclohexylmethyl)-5-[(4-fluorophenyl)methyl]-11-hydroxy-4-sulfanylidene-8-oxa-3,5-diazatricyclo[5.2.2.02,6]undecan-9-one
—— (3,6-Dimethyl-9-methylidene-2-oxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl) acetate —— C17H20O4
(3,6-Dimethyl-9-methylidene-2-oxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl) acetate
—— 14-Methyl-5,9-dimethylidene-3,13-dioxatricyclo[8.4.0.02,6]tetradecane-4,12-dione —— C15H18O4
14-Methyl-5,9-dimethylidene-3,13-dioxatricyclo[8.4.0.02,6]tetradecane-4,12-dione
—— 4-(2-Methyl-5-oxooxolan-2-yl)cyclohexene-1-carboxylic acid —— C12H16O4
4-(2-Methyl-5-oxooxolan-2-yl)cyclohexene-1-carboxylic acid
—— 4,4-Dimethyl-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxolan-2-one —— C12H20O8
4,4-Dimethyl-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxolan-2-one
—— 6-Tricosyloxan-2-one —— C28H54O2
6-Tricosyloxan-2-one
—— 5'-(Furan-3-yl)-6-hydroxy-12-(hydroxymethyl)-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4-ene-9,3'-oxolane]-2',3-dione —— C20H22O7
5'-(Furan-3-yl)-6-hydroxy-12-(hydroxymethyl)-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4-ene-9,3'-oxolane]-2',3-dione
—— 4-Hydroxy-5-methyl-3-(10-oxo-2-propan-2-ylundec-1-enyl)oxolan-2-one —— C19H32O4
4-Hydroxy-5-methyl-3-(10-oxo-2-propan-2-ylundec-1-enyl)oxolan-2-one
—— (2,3-Dimethyl-6-oxooxan-4-yl)methyl 2-methylbutanoate —— C13H22O4
(2,3-Dimethyl-6-oxooxan-4-yl)methyl 2-methylbutanoate
—— 4-Hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-2-one —— C15H16O3
4-Hydroxy-6,9-dimethyl-3-methylidene-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-2-one
—— 3-(4-(diethylamino)but-2-ynyl)-5-pentyldihydrofuran-2(3H)-one —— C17H29NO2
3-(4-(diethylamino)but-2-ynyl)-5-pentyldihydrofuran-2(3H)-one
—— 1-(3-Methyl-5-oxooxolan-2-yl)oct-2-en-4-yl acetate —— C15H24O4
1-(3-Methyl-5-oxooxolan-2-yl)oct-2-en-4-yl acetate
—— 2-(Hydroxymethyl)-5,5-dimethyl-11-oxatetracyclo[7.3.1.01,9.03,7]tridec-3(7)-ene-4,10-dione —— C15H18O4
2-(Hydroxymethyl)-5,5-dimethyl-11-oxatetracyclo[7.3.1.01,9.03,7]tridec-3(7)-ene-4,10-dione
—— 3-(Dimethoxymethyl)-1-(3-methylbut-2-enyl)-6-oxabicyclo[3.2.0]hept-2-en-7-one —— C14H20O4
3-(Dimethoxymethyl)-1-(3-methylbut-2-enyl)-6-oxabicyclo[3.2.0]hept-2-en-7-one
—— (2aR,4aS,5R,8S,8aS,8bS,9R)-Octahydro-2a,9-dihydroxy-8b-methyl-9-(1-methylethyl)-5,8-methano-1,7-dioxacyclopent[cd]azulene-2,6-dione 70219-70-4 C15H20O6
(2aR,4aS,5R,8S,8aS,8bS,9R)-Octahydro-2a,9-dihydroxy-8b-methyl-9-(1-methylethyl)-5,8-methano-1,7-dioxacyclopent[cd]azulene-2,6-dione
—— (3aR,4aS,5R,9aS)-5,8-Dimethyl-3-methylene-3a,4,4a,5,6,7,9,9a-octahydroazuleno[6,5-b]furan-2(3H)-one —— C15H20O2
(3aR,4aS,5R,9aS)-5,8-Dimethyl-3-methylene-3a,4,4a,5,6,7,9,9a-octahydroazuleno[6,5-b]furan-2(3H)-one
—— 4-Hydroxy-7-(2-hydroxypropyl)-3-methyloxepan-2-one —— C10H18O4
4-Hydroxy-7-(2-hydroxypropyl)-3-methyloxepan-2-one
—— 6-(Furan-3-yl)-1,9,14-trimethyl-4,7,16-trioxapentacyclo[9.5.0.02,14.03,5.05,10]hexadec-9-ene-8,15-dione —— C20H20O6
6-(Furan-3-yl)-1,9,14-trimethyl-4,7,16-trioxapentacyclo[9.5.0.02,14.03,5.05,10]hexadec-9-ene-8,15-dione
—— 2-(2,3,6,7-Tetramethyl-9-oxo-10,11-dioxatricyclo[6.2.1.02,6]undecan-8-yl)acetaldehyde —— C15H22O4
2-(2,3,6,7-Tetramethyl-9-oxo-10,11-dioxatricyclo[6.2.1.02,6]undecan-8-yl)acetaldehyde
—— 5-Octacosyloxolan-2-one —— C32H62O2
5-Octacosyloxolan-2-one
—— 2,5,13-Trihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione —— C15H22O6
2,5,13-Trihydroxy-2,6,13-trimethyl-8-oxatricyclo[4.4.3.01,5]tridecane-9,12-dione
—— Methyl 2-[14-(furan-3-yl)-17-hydroxy-2,7,7,9,13-pentamethyl-6,16-dioxo-3,15-dioxapentacyclo[8.7.0.01,13.02,10.04,9]heptadec-4-en-8-yl]acetate —— C27H32O8
Methyl 2-[14-(furan-3-yl)-17-hydroxy-2,7,7,9,13-pentamethyl-6,16-dioxo-3,15-dioxapentacyclo[8.7.0.01,13.02,10.04,9]heptadec-4-en-8-yl]acetate
—— Diplodialide C —— C10H18O3
Diplodialide C
—— 10-methyl-6-dodecanolide —— C13H24O2
10-methyl-6-dodecanolide
—— {5-[2-(4-hydroxy-2-oxooxolan-3-ylidene)ethyl]-1-(hydroxymethyl)-1,4a-dimethyl-6-methylidene-decahydronaphthalen-2-yl}hydrogenio sulfuric acid —— —— ——
—— 5-[2-Ethenyl-4-(hydroxymethyl)-4-methylcyclopentylidene]-4-(hydroxymethyl)oxan-2-one —— C15H22O4
5-[2-Ethenyl-4-(hydroxymethyl)-4-methylcyclopentylidene]-4-(hydroxymethyl)oxan-2-one
—— methyl 1-hydroxy-5,5,7a,9,12,12a,13b-heptamethyl-3,10-dioxo-2,5a,6,7,13,13a-hexahydro-1H-oxepino[4,3-a]xanthene-11-carboxylate —— C26H36O7
methyl 1-hydroxy-5,5,7a,9,12,12a,13b-heptamethyl-3,10-dioxo-2,5a,6,7,13,13a-hexahydro-1H-oxepino[4,3-a]xanthene-11-carboxylate
—— 5-(4-Hydroxy-4-methylpentyl)oxolan-2-one —— C10H18O3
5-(4-Hydroxy-4-methylpentyl)oxolan-2-one
—— 4-Hydroxy-8,14-dimethyl-2-oxatetracyclo[9.2.1.04,13.07,12]tetradec-5-en-3-one —— C15H20O3
4-Hydroxy-8,14-dimethyl-2-oxatetracyclo[9.2.1.04,13.07,12]tetradec-5-en-3-one
—— 3-(2-Hydroxyethyl)-5-(2-hydroxypropyl)oxolan-2-one —— C9H16O4
3-(2-Hydroxyethyl)-5-(2-hydroxypropyl)oxolan-2-one
—— [2-oxo-4-(1,3,3-trimethylcyclohexyl)-3,5,6,7,7a,7b-hexahydro-2aH-indeno[1,2-b]oxet-7-yl]methyl 3-methylbutanoate —— C25H38O4
[2-oxo-4-(1,3,3-trimethylcyclohexyl)-3,5,6,7,7a,7b-hexahydro-2aH-indeno[1,2-b]oxet-7-yl]methyl 3-methylbutanoate
—— 4'-hydroxy-5'-methoxy-3,3,6-trimethylspiro[3a,4,5,7a-tetrahydro-1H-indene-2,3'-oxolane]-2'-one —— C16H24O4
4'-hydroxy-5'-methoxy-3,3,6-trimethylspiro[3a,4,5,7a-tetrahydro-1H-indene-2,3'-oxolane]-2'-one
—— 5-Oxo-tetrahydro-furan-2-carboxylic acid dimethylamide —— C7H11NO3
5-Oxo-tetrahydro-furan-2-carboxylic acid dimethylamide
—— 10-Ethoxy-4,7,13,13-tetramethyl-18-oxapentacyclo[9.5.2.01,12.02,9.04,8]octadeca-2(9),6-diene-3,5,17-trione —— C23H28O5
10-Ethoxy-4,7,13,13-tetramethyl-18-oxapentacyclo[9.5.2.01,12.02,9.04,8]octadeca-2(9),6-diene-3,5,17-trione
—— Methyl 2-[14-(furan-3-yl)-11,17-dihydroxy-2,7,7,9,13-pentamethyl-6,16-dioxo-3,15-dioxapentacyclo[8.7.0.01,13.02,10.04,9]heptadec-4-en-8-yl]acetate —— C27H32O9
Methyl 2-[14-(furan-3-yl)-11,17-dihydroxy-2,7,7,9,13-pentamethyl-6,16-dioxo-3,15-dioxapentacyclo[8.7.0.01,13.02,10.04,9]heptadec-4-en-8-yl]acetate
—— 3-Butyryl-4-hydroxymethyl-dihydro-furan-2-one —— C9H14O4
3-Butyryl-4-hydroxymethyl-dihydro-furan-2-one
—— 5-Dec-9-enyl-3-(2,3-dimethoxy-propyl)-dihydro-furan-2-one 62949-83-1 C19H34O4
5-Dec-9-enyl-3-(2,3-dimethoxy-propyl)-dihydro-furan-2-one
—— 6-Hydroxy-3,6,9-trimethyl-3a,5,6,6a,7,9b-hexahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione —— C15H20O4
6-Hydroxy-3,6,9-trimethyl-3a,5,6,6a,7,9b-hexahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione
—— 6-Hydroxy-5,5,11,15-tetramethyl-9-phenyl-8-oxapentacyclo[13.2.1.01,12.04,11.06,10]octadec-16-ene-7,14-dione —— C27H32O4
6-Hydroxy-5,5,11,15-tetramethyl-9-phenyl-8-oxapentacyclo[13.2.1.01,12.04,11.06,10]octadec-16-ene-7,14-dione
—— Illicinolide A 131917-04-9 C16H24O8
Illicinolide A
—— [9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] acetate —— C17H18O6
[9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] acetate
—— 3-Dodec-11-enylidene-4-hydroxy-5-methyloxolan-2-one —— C17H28O3
3-Dodec-11-enylidene-4-hydroxy-5-methyloxolan-2-one
—— Methyl 2-[4-[8-(furan-3-yl)-1,4-dihydroxy-4,9-dimethyl-6,12-dioxo-3,7-dioxatricyclo[7.3.1.05,13]tridecan-2-yl]-2,2,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate —— C29H36O10
Methyl 2-[4-[8-(furan-3-yl)-1,4-dihydroxy-4,9-dimethyl-6,12-dioxo-3,7-dioxatricyclo[7.3.1.05,13]tridecan-2-yl]-2,2,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
—— 9a-Hydroxy-6-methyl-3,9-dimethylidene-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-2-one —— C15H16O3
9a-Hydroxy-6-methyl-3,9-dimethylidene-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-2-one
—— 12-Hydroxy-2,8,12-trimethyl-3,6-dioxatetracyclo[9.3.0.02,4.05,9]tetradecan-7-one —— C15H22O4
12-Hydroxy-2,8,12-trimethyl-3,6-dioxatetracyclo[9.3.0.02,4.05,9]tetradecan-7-one
—— 9-[2-(Furan-3-yl)ethyl]-5-hydroxy-9,10,12-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one —— C20H28O4
9-[2-(Furan-3-yl)ethyl]-5-hydroxy-9,10,12-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one
—— 5-Hydroxy-6-methyl-2,10-dimethylidene-12-oxatricyclo[7.3.1.01,5]tridecan-11-one —— C15H20O3
5-Hydroxy-6-methyl-2,10-dimethylidene-12-oxatricyclo[7.3.1.01,5]tridecan-11-one