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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
—— [(3S,3aS,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-chloroacetate —— C17H19ClO5
[(3S,3aS,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-chloroacetate
—— 2-Oxabicyclo[2.2.1]heptan-3-one-1-carboxylic acid, 4,7,7-trimethyl-, 8-oxo-8a-methyldecalin-1-yl ester —— C21H30O5
2-Oxabicyclo[2.2.1]heptan-3-one-1-carboxylic acid, 4,7,7-trimethyl-, 8-oxo-8a-methyldecalin-1-yl ester
—— (3R,6Z)-6-(bromomethylidene)-3-phenyloxan-2-one —— C12H11BrO2
(3R,6Z)-6-(bromomethylidene)-3-phenyloxan-2-one
—— 2H-Pyran-2-one, 4-[(tert-butyldimethylsilyl)oxy]tetrahydro-4-methyl- —— C12H24O3Si
2H-Pyran-2-one, 4-[(tert-butyldimethylsilyl)oxy]tetrahydro-4-methyl-
—— 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid, 9-oxa-bicyclo[3.3.1]non-6-en-2-yl ester —— C18H24O5
4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid, 9-oxa-bicyclo[3.3.1]non-6-en-2-yl ester
—— 6-Oxabicyclo[3.2.1]nonan-7-one, 1,3,5-trimethyl- —— C10H16O2
6-Oxabicyclo[3.2.1]nonan-7-one, 1,3,5-trimethyl-
—— trans-4,6,6-Trimethyl-7-oxo-8-oxabicyclo(2.2.2)octane-2-carboxylic acid —— C11H16O4
trans-4,6,6-Trimethyl-7-oxo-8-oxabicyclo(2.2.2)octane-2-carboxylic acid
—— 9-Hydroxy-3-methoxymethyl-4,9-dimethyl-1,7-dioxa-spiro[4.4]nonane-2,8-dione 54370-16-0 C11H16O6
9-Hydroxy-3-methoxymethyl-4,9-dimethyl-1,7-dioxa-spiro[4.4]nonane-2,8-dione
—— (3R)-3-butyl-N-carbamothioyl-2-oxooxolane-3-carboxamide —— C10H16N2O3S
(3R)-3-butyl-N-carbamothioyl-2-oxooxolane-3-carboxamide
—— 1-(5-Bromo-2-furyl)-4,4-dimethyl-2-oxaspiro[5.5]undecane-3,5-dione —— C16H19BrO4
1-(5-Bromo-2-furyl)-4,4-dimethyl-2-oxaspiro[5.5]undecane-3,5-dione
—— 4,5-Dichlorooxolan-2-one —— C4H4Cl2O2
4,5-Dichlorooxolan-2-one
—— cis-2-Chloro-4-pentanolide —— C5H7ClO2
cis-2-Chloro-4-pentanolide
—— 3-(2-ethoxyethyl)-5-methyloxolan-2-one —— C9H16O3
3-(2-ethoxyethyl)-5-methyloxolan-2-one
—— tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid 22073-04-7 C6H8O4
tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid
—— (5S)-3,3-dichloro-5-methyloxolan-2-one —— C5H6Cl2O2
(5S)-3,3-dichloro-5-methyloxolan-2-one
—— 3,3-dibromodihydro-5-methylfuran-2(3H)-one 32366-01-1 C5H6Br2O2
3,3-dibromodihydro-5-methylfuran-2(3H)-one
—— 4-Bromo-4-methyl-5-oxo-tetrahydro-furan-2-carboxylic acid —— C6H7BrO4
4-Bromo-4-methyl-5-oxo-tetrahydro-furan-2-carboxylic acid
—— (6-Ethylthio-3-oxo-2-oxabicyclo[3.3.1]non-7-yl)acetic acid, methyl ester —— C13H20O4S
(6-Ethylthio-3-oxo-2-oxabicyclo[3.3.1]non-7-yl)acetic acid, methyl ester
—— (5R)-5-[(2R)-6-methoxy-6-methylheptan-2-yl]oxolan-2-one —— C13H24O3
(5R)-5-[(2R)-6-methoxy-6-methylheptan-2-yl]oxolan-2-one
—— (5S)-5-[(2R)-6-methoxy-6-methylheptan-2-yl]oxolan-2-one —— C13H24O3
(5S)-5-[(2R)-6-methoxy-6-methylheptan-2-yl]oxolan-2-one
—— 2-Furancarboxylic acid, tetrahydro-3-methyl-5-oxo-, methyl ester 85547-53-1 C7H10O4
2-Furancarboxylic acid, tetrahydro-3-methyl-5-oxo-, methyl ester
—— (5R)-5-[(2R)-6-methylhept-5-en-2-yl]oxolan-2-one —— C12H20O2
(5R)-5-[(2R)-6-methylhept-5-en-2-yl]oxolan-2-one
—— (5R)-3,3,5-trimethyloxepan-2-one —— C9H16O2
(5R)-3,3,5-trimethyloxepan-2-one
—— (5S)-5-[(2R)-6-methylhept-5-en-2-yl]oxolan-2-one —— C12H20O2
(5S)-5-[(2R)-6-methylhept-5-en-2-yl]oxolan-2-one
—— 7-Oxabicyclo[4.2.1]nona-2,4-dien-8-one, 9-methyl- —— C9H10O2
7-Oxabicyclo[4.2.1]nona-2,4-dien-8-one, 9-methyl-
—— (5S)-3,3,5-trimethyloxepan-2-one —— C9H16O2
(5S)-3,3,5-trimethyloxepan-2-one
—— (5R)-3,3-dichloro-5-methyloxolan-2-one —— C5H6Cl2O2
(5R)-3,3-dichloro-5-methyloxolan-2-one
—— (5R)-3,3-dibromo-5-methyloxolan-2-one —— C5H6Br2O2
(5R)-3,3-dibromo-5-methyloxolan-2-one
—— 6,8b-Ethano-8bH-cyclopenta[de]-2-benzopyran-1-one, 4-(ethylenedioxy)octahydro-8a-hydroxy-10,10-dimethyl-, [3aS-(3aalpha,5abeta,6alpha,8aalpha,8balpha)]- —— C17H24O5
6,8b-Ethano-8bH-cyclopenta[de]-2-benzopyran-1-one, 4-(ethylenedioxy)octahydro-8a-hydroxy-10,10-dimethyl-, [3aS-(3aalpha,5abeta,6alpha,8aalpha,8balpha)]-
—— (5R)-5-[(2S)-6-methylhept-5-en-2-yl]oxolan-2-one —— C12H20O2
(5R)-5-[(2S)-6-methylhept-5-en-2-yl]oxolan-2-one
—— 2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-3a-(2-phenylethyl)- 69687-97-4 C15H18O3
2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-3a-(2-phenylethyl)-
—— (5S)-5-[(2S)-6-methoxy-6-methylheptan-2-yl]oxolan-2-one —— C13H24O3
(5S)-5-[(2S)-6-methoxy-6-methylheptan-2-yl]oxolan-2-one
—— 2H-Pyran-2,4(3H)-dione, 5-ethyl-3,3-dimethyl-6-phenyl- —— C15H18O3
2H-Pyran-2,4(3H)-dione, 5-ethyl-3,3-dimethyl-6-phenyl-
—— 4,4a,6,7,8,8a-hexahydro-3H-pyrano[3,2-b]pyran-2-one —— C8H12O3
4,4a,6,7,8,8a-hexahydro-3H-pyrano[3,2-b]pyran-2-one
—— Coumarine, 3,4,5,6-tetrahydro-6,8a-epidioxy-4a-methyl- —— C10H12O4
Coumarine, 3,4,5,6-tetrahydro-6,8a-epidioxy-4a-methyl-
—— 6-(2-Fluoro-phenyl)-3,3,5,5-tetramethyl-dihydro-pyran-2,4-dione —— C15H17FO3
6-(2-Fluoro-phenyl)-3,3,5,5-tetramethyl-dihydro-pyran-2,4-dione
—— 3-Oxabicyclo[3.3.0]octane-2,7-dione, 4-methoxy-, trans- —— C8H10O4
3-Oxabicyclo[3.3.0]octane-2,7-dione, 4-methoxy-, trans-
—— d-Lyxo-d-manno-nononic-1,4-lactone —— C9H16O9
d-Lyxo-d-manno-nononic-1,4-lactone
—— 6,6-dimethyl-3-(methylaminomethylidene)oxane-2,4-dione —— C9H13NO3
6,6-dimethyl-3-(methylaminomethylidene)oxane-2,4-dione
—— 3-[(6,6-dimethyl-2,4-dioxooxan-3-ylidene)methyl-methylamino]propanenitrile —— C12H16N2O3
3-[(6,6-dimethyl-2,4-dioxooxan-3-ylidene)methyl-methylamino]propanenitrile
—— 3-(Dimethylaminomethylidene)-5,5-dimethyloxolane-2,4-dione —— C9H13NO3
3-(Dimethylaminomethylidene)-5,5-dimethyloxolane-2,4-dione
—— (3S)-3-hydroxy-3-methyl-5,5-bis(trifluoromethyl)oxolan-2-one —— C7H6F6O3
(3S)-3-hydroxy-3-methyl-5,5-bis(trifluoromethyl)oxolan-2-one
—— (4S,5S)-4-methyl-5-propyloxolane-2,3-dione —— C8H12O3
(4S,5S)-4-methyl-5-propyloxolane-2,3-dione
—— (4S,5R)-4-methyl-5-propyloxolane-2,3-dione —— C8H12O3
(4S,5R)-4-methyl-5-propyloxolane-2,3-dione
—— (1S,7S,8R)-7-(2-Hydroxyethyl)-1,6,8-trimethyl-3-oxatricyclo[6.3.1.0<4,12>]dodec-5-en-2-one —— C16H24O3
(1S,7S,8R)-7-(2-Hydroxyethyl)-1,6,8-trimethyl-3-oxatricyclo[6.3.1.0<4,12>]dodec-5-en-2-one
—— (5S)-5-methyl-5-pentyloxolan-2-one —— C10H18O2
(5S)-5-methyl-5-pentyloxolan-2-one
—— (5R)-5-butyl-5-ethyloxolan-2-one —— C10H18O2
(5R)-5-butyl-5-ethyloxolan-2-one
—— (3R)-3-pentyloxan-2-one —— C10H18O2
(3R)-3-pentyloxan-2-one
—— (5R)-5-methyl-5-pentyloxolan-2-one —— C10H18O2
(5R)-5-methyl-5-pentyloxolan-2-one
—— (5S)-3,3-dichloro-5-pentyloxolan-2-one —— C9H14Cl2O2
(5S)-3,3-dichloro-5-pentyloxolan-2-one