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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
—— 4,5,5-trimethyl-2-oxotetrahydrofuran-3-carboxamide 13134-06-0 C8H13NO3
4,5,5-trimethyl-2-oxotetrahydrofuran-3-carboxamide
—— (3aS,6aS)-3a-Methyl-hexahydro-cyclopenta[b]furan-2-one 39778-83-1 C8H12O2
(3aS,6aS)-3a-Methyl-hexahydro-cyclopenta[b]furan-2-one
—— (+/-)-Prelog-Djerassi lactonic acid 80226-06-8 C10H16O4
(+/-)-Prelog-Djerassi lactonic acid
—— (4S,2'S,4'R)-2,2-dimethyl-4-(4-methyl-5-oxotetrahydrofuran-2-yl)oxazolidine-3-carboxylic acid tert-butyl ester 906662-78-0 C15H25NO5
(4S,2'S,4'R)-2,2-dimethyl-4-(4-methyl-5-oxotetrahydrofuran-2-yl)oxazolidine-3-carboxylic acid tert-butyl ester
—— (3R,4S)-3-hydroxy-4-methyl-5-pentanolide 97690-86-3 C6H10O3
(3R,4S)-3-hydroxy-4-methyl-5-pentanolide
—— 5Z-octenolide —— C8H12O2
5Z-octenolide
—— (4R,5S,3Z)-5-Prop-2-enyl-4-(tert-butyldimethylsilyloxy)-3-[(R)-3-(2,2-dimethoxyethyl)-4-methyl-pent-4-en-1-ylidene]dihydrofuran-2(3H)-one 1552276-01-3 C23H40O5Si
(4R,5S,3Z)-5-Prop-2-enyl-4-(tert-butyldimethylsilyloxy)-3-[(R)-3-(2,2-dimethoxyethyl)-4-methyl-pent-4-en-1-ylidene]dihydrofuran-2(3H)-one
—— γ,δ-Cycloheptano-δ-valerolacton 771-96-0 C10H16O2
γ,δ-Cycloheptano-δ-valerolacton
—— methyl 1,6,8-trimethyl-4,10-dioxo-5-oxatricyclo<4,3,1,0<sup>3,7</sup>>dec-8-ene-5,6-dicarboxylate 73195-07-0 C14H16O5
methyl 1,6,8-trimethyl-4,10-dioxo-5-oxatricyclo<4,3,1,0<sup>3,7</sup>>dec-8-ene-5,6-dicarboxylate
—— 5-(2-Bromoethyl)-5-pentanolide 152668-02-5 C7H11BrO2
5-(2-Bromoethyl)-5-pentanolide
—— tert-butyl (5-oxo-4-oxatricyclo[4.3.1.1(3,8)]undecan-1-yl)carbamate 1414379-62-6 C15H23NO4
tert-butyl (5-oxo-4-oxatricyclo[4.3.1.1(3,8)]undecan-1-yl)carbamate
—— N-(5-oxo-4-oxatricyclo[4.3.1.1(3,8)]undecan-1-yl)acetamide 502421-65-0 C12H17NO3
N-(5-oxo-4-oxatricyclo[4.3.1.1(3,8)]undecan-1-yl)acetamide
—— [5,5,6,6,6-(2)H5]mevalonolactone 1313206-79-9 C6H10O3
[5,5,6,6,6-(2)H5]mevalonolactone
—— 3RS-<5-D(1)>mevalonolacton 10012-92-7 C6H10O3
3RS-<5-D(1)>mevalonolacton
—— 2-methyl-5-oxo-N,N-dipropyloxolane-2-carboxamide 6946-47-0 C12H21NO3
2-methyl-5-oxo-N,N-dipropyloxolane-2-carboxamide
—— (R)-3-((2R,3S,4R,5S)-4-Hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2-triisopropylsilanyloxy-propionaldehyde 153402-91-6 C19H36O5Si
(R)-3-((2R,3S,4R,5S)-4-Hydroxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2-triisopropylsilanyloxy-propionaldehyde
—— 5-Ethylfuran-2,4(3h,5h)-dione 36717-59-6 C6H8O3
5-Ethylfuran-2,4(3h,5h)-dione
—— 5-phenyloxepan-2-one 252888-52-1 C12H14O2
5-phenyloxepan-2-one
—— 5-phenyloxepan-2-one 252888-53-2 C12H14O2
5-phenyloxepan-2-one
—— 8-butyloxocan-2-one 1421750-60-8 C11H20O2
8-butyloxocan-2-one
—— (S)-7-methylheptalactone 126372-23-4 C8H14O2
(S)-7-methylheptalactone
—— 5,5-(Ethylendioxy)-2,2-dimethylcyclohexan-1,3-dicarbonsaeureanhydrid 92694-97-8 C12H16O5
5,5-(Ethylendioxy)-2,2-dimethylcyclohexan-1,3-dicarbonsaeureanhydrid
—— Octahydro-2h-naphtho[1,8-bc]furan-2,6(2ah)-dione 19592-87-1 C11H14O3
Octahydro-2h-naphtho[1,8-bc]furan-2,6(2ah)-dione
—— 3-Acetyl-5-isopropyl-4,4,5-trimethyl-dihydro-furan-2-one 127236-67-3 C12H20O3
3-Acetyl-5-isopropyl-4,4,5-trimethyl-dihydro-furan-2-one
—— 5-Isopropyl-4,4,5-trimethyl-dihydro-furan-2-one 137008-52-7 C10H18O2
5-Isopropyl-4,4,5-trimethyl-dihydro-furan-2-one
—— (4S,5S)-4-Methoxymethoxy-5-methyl-3-tetradec-(E)-ylidene-dihydro-furan-2-one 303008-39-1 C21H38O4
(4S,5S)-4-Methoxymethoxy-5-methyl-3-tetradec-(E)-ylidene-dihydro-furan-2-one
—— 3,3,6-Trimethyl-dihydro-pyran-2,4-dione 87442-63-5 C8H12O3
3,3,6-Trimethyl-dihydro-pyran-2,4-dione
—— 3-acetyl-5,5-diisopropyldihydro-2(3H)-furanone 127236-68-4 C12H20O3
3-acetyl-5,5-diisopropyldihydro-2(3H)-furanone
—— marliolide 111900-39-1 C19H34O3
marliolide
—— 2-acetyl-[3,3,4,4-2H4]butane-4-lactone 476646-93-2 C6H8O3
2-acetyl-[3,3,4,4-2H4]butane-4-lactone
—— 3-(2-Chloro-2-methylethyl)-4-hydroxybutyric acid lactone 96546-91-7 C7H11ClO2
3-(2-Chloro-2-methylethyl)-4-hydroxybutyric acid lactone
—— 2,2-Dichloro-3-(2-chloro-2-methylethyl)-4-hydroxybutyric acid lactone 96546-90-6 C7H9Cl3O2
2,2-Dichloro-3-(2-chloro-2-methylethyl)-4-hydroxybutyric acid lactone
—— 1-bromo-6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one 1632155-60-2 C7H9BrO2
1-bromo-6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one
—— 6-formyl-3-oxa-bicyclo[3.1.0]hexane-2-one —— C6H6O3
6-formyl-3-oxa-bicyclo[3.1.0]hexane-2-one
—— (2R,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 19473-19-9 C5H8O4
(2R,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide
—— 5-trifluoromethyl-5-trimethylsilyloxy-γ-butyrolactone 370103-95-0 C8H13F3O3Si
5-trifluoromethyl-5-trimethylsilyloxy-γ-butyrolactone
—— 4-(1-methylethylidene)tetrahydrofuran-2-one 102939-66-2 C7H10O2
4-(1-methylethylidene)tetrahydrofuran-2-one
—— 2-methyl-4,5-dehydro ε-lactone 1092695-33-4 C7H10O2
2-methyl-4,5-dehydro ε-lactone
—— (1S,4R,5S,8S)-2-benzyl-8-fluoromethyl-4-methyl-3,7-dioxa-1-azabicyclo[3.3.0]octan-6-one 200569-57-9 C14H16FNO3
(1S,4R,5S,8S)-2-benzyl-8-fluoromethyl-4-methyl-3,7-dioxa-1-azabicyclo[3.3.0]octan-6-one
—— (2-oxo-tetrahydro-pyran-3-yl)-acetaldehyde 1033272-70-6 C7H10O3
(2-oxo-tetrahydro-pyran-3-yl)-acetaldehyde
—— pseudoivalin 1461-34-3 C15H20O3
pseudoivalin
—— 4-phenyl-7a,8-dihydrothieno[2,3-f]isobenzofuran-5(7H)-one 3216-46-4 C16H12O2S
4-phenyl-7a,8-dihydrothieno[2,3-f]isobenzofuran-5(7H)-one
—— 4-Ethyl-3-methylene-1-oxetan-2-one 117203-17-5 C6H8O2
4-Ethyl-3-methylene-1-oxetan-2-one
—— 5-(2-Bromo-ethyl)-3-methylene-dihydro-furan-2-one 79937-98-7 C7H9BrO2
5-(2-Bromo-ethyl)-3-methylene-dihydro-furan-2-one
—— (1S,4S,5R)-1-chloro-4-hydroxymethyl-3-oxabicyclo[3.2.0]heptan-2-one 1311267-48-7 C7H9ClO3
(1S,4S,5R)-1-chloro-4-hydroxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
—— (6R,7R)-7-chloro-6-hydroxymethyl-5-oxaspiro[2.4]heptan-4-one 1311267-52-3 C7H9ClO3
(6R,7R)-7-chloro-6-hydroxymethyl-5-oxaspiro[2.4]heptan-4-one
—— (1S,4S,5R)-4-tert-butyldimethylsilyloxymethyl-1-chloro-3-oxabicyclo[3.2.0]heptan-2-one 1311267-88-5 C13H23ClO3Si
(1S,4S,5R)-4-tert-butyldimethylsilyloxymethyl-1-chloro-3-oxabicyclo[3.2.0]heptan-2-one
—— (6R,7S)-7-chloro-6-hydroxymethyl-5-oxaspiro[2.4]heptan-4-one 1311267-53-4 C7H9ClO3
(6R,7S)-7-chloro-6-hydroxymethyl-5-oxaspiro[2.4]heptan-4-one
—— (3S,4S)-4-[(E,2R)-2-[tert-butyl(dimethyl)silyl]oxyhept-5-enyl]-3-hexyloxetan-2-one 1026486-59-8 C22H42O3Si
(3S,4S)-4-[(E,2R)-2-[tert-butyl(dimethyl)silyl]oxyhept-5-enyl]-3-hexyloxetan-2-one
—— [(1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(2S,3S)-3-methoxy-6-oxooxan-2-yl]ethyl] 2,2-dimethylpropanoate 1032880-02-6 C29H40O6Si
[(1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(2S,3S)-3-methoxy-6-oxooxan-2-yl]ethyl] 2,2-dimethylpropanoate