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    首页 分子通 按分子结构分类 有机化合物 有机杂环化合物 内酯类

    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
    —— (3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile 1491026-38-0 C7H9NO4
    (3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methyl-2-oxooxolane-3-carbonitrile
    —— 3-ethoxy-tetrahydrofuran-2-one 25600-26-4 C6H10O3
    3-ethoxy-tetrahydrofuran-2-one
    —— opt.-inaktiv 3-(1-Hydroxy-2,2,6-trimethyl-cyclohexyl)-propionsaeure-lacton 64108-16-3 C12H20O2
    opt.-inaktiv 3-(1-Hydroxy-2,2,6-trimethyl-cyclohexyl)-propionsaeure-lacton
    —— (+/-)-Homoterpenylsaeure 4437-42-7 C9H14O4
    (+/-)-Homoterpenylsaeure
    —— 4-acetoxy-5-ethyl-3-methylene-dihydro-furan-2-one 76299-61-1 C9H12O4
    4-acetoxy-5-ethyl-3-methylene-dihydro-furan-2-one
    —— α-Aethyl-γ-phenyl-butyrolacton 54491-06-4 C12H14O2
    α-Aethyl-γ-phenyl-butyrolacton
    —— (3S,4S,5S)-3-Chloro-5-hydroxymethyl-4-vinyl-dihydro-furan-2-one 176980-73-7 C7H9ClO3
    (3S,4S,5S)-3-Chloro-5-hydroxymethyl-4-vinyl-dihydro-furan-2-one
    —— δ-decanolactone 63450-32-8 C10H18O2
    δ-decanolactone
    —— (S)-2-((2S,3S,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionic acid 69779-58-4 C10H16O4
    (S)-2-((2S,3S,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionic acid
    —— (R)-dihydro-5-((R)-hydroxy(phenyl)methyl)furan-2(3H)-one 445396-74-7 C11H12O3
    (R)-dihydro-5-((R)-hydroxy(phenyl)methyl)furan-2(3H)-one
    —— (5S)-3-cyclohexylsulfanyl-5-ethyl-dihydrofuran-2-one 890706-54-4 C12H20O2S
    (5S)-3-cyclohexylsulfanyl-5-ethyl-dihydrofuran-2-one
    —— (R)-(-)-4-Isopropyl-4-methylbutan-4-olide 60646-31-3 C8H14O2
    (R)-(-)-4-Isopropyl-4-methylbutan-4-olide
    —— 4-Methylen-dihydro-spiro<furan-2,3'-thujan>-5'-on 97945-94-3 C14H20O2
    4-Methylen-dihydro-spiro<furan-2,3'-thujan>-5'-on
    —— Methyl 4-(cyanomethyl)-5,5-dimethyl-2-oxooxolane-3-carboxylate 155887-47-1 C10H13NO4
    Methyl 4-(cyanomethyl)-5,5-dimethyl-2-oxooxolane-3-carboxylate
    —— 3-(methoxycarbonylmethyl)-1-oxaspiro<4.4>nonan-2-one 138842-53-2 C11H16O4
    3-(methoxycarbonylmethyl)-1-oxaspiro<4.4>nonan-2-one
    —— 4-methyl-2-(methoxycarbonylmethyl)-4-decanolide 138842-54-3 C14H24O4
    4-methyl-2-(methoxycarbonylmethyl)-4-decanolide
    —— rel-(3R)-(5E)-3-<rel-(1S)-1-Hydroxy-3-methyl-3-butenyl>-6,8-dimethyl-5,8-nonadienoic Acid γ-Lactone 88377-10-0 C16H24O2
    rel-(3R)-(5E)-3-<rel-(1S)-1-Hydroxy-3-methyl-3-butenyl>-6,8-dimethyl-5,8-nonadienoic Acid γ-Lactone
    —— rel-(3S,5R)-6-Methyl-5-hydroxy-3-vinyl-6-heptenoic Acid Lactone 88376-91-4 C10H14O2
    rel-(3S,5R)-6-Methyl-5-hydroxy-3-vinyl-6-heptenoic Acid Lactone
    —— rel-(3S,5S)-3-Vinyl-5-hydroxy-6-methyl-6-heptenoic Acid Lactone 88376-96-9 C10H14O2
    rel-(3S,5S)-3-Vinyl-5-hydroxy-6-methyl-6-heptenoic Acid Lactone
    —— (3S,4R)-3,5-dimethyl-4-hexanolide 118759-58-3 C8H14O2
    (3S,4R)-3,5-dimethyl-4-hexanolide
    —— 3-(2-(2-ethylphenyl)-2-(triethylsilylperoxy)ethyl)-3-methyldihydrofuran-2(3H)-one 1321200-23-0 C21H34O4Si
    3-(2-(2-ethylphenyl)-2-(triethylsilylperoxy)ethyl)-3-methyldihydrofuran-2(3H)-one
    —— (R*,R*)-2-<(2-ethylphenyl)hydroxymethyl>-6-hexanolide 139367-43-4 C15H20O3
    (R*,R*)-2-<(2-ethylphenyl)hydroxymethyl>-6-hexanolide
    —— (1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid 263169-43-3 C6H5BrO4
    (1S,5R,6R)-1-bromo-4-oxabicyclo[3.1.0]hexane-6-carboxylic acid
    —— (1R,3R,4R)-1,4-bis(tert-butyldimethylsilyloxy)-5-phenylcyclohex-5-ene-1,3-carbolactone 862791-32-0 C25H40O4Si2
    (1R,3R,4R)-1,4-bis(tert-butyldimethylsilyloxy)-5-phenylcyclohex-5-ene-1,3-carbolactone
    —— (1R,3R,4R)-1,4-dihydroxy-5-(furan-3-yl)cyclohex-5-ene-1,3-carbolactone 862791-89-7 C11H10O5
    (1R,3R,4R)-1,4-dihydroxy-5-(furan-3-yl)cyclohex-5-ene-1,3-carbolactone
    —— (1R,3R,4R)-1,4-dihydroxy-5-phenylcyclohex-5-ene-1,3-carbolactone 862791-64-8 C13H12O4
    (1R,3R,4R)-1,4-dihydroxy-5-phenylcyclohex-5-ene-1,3-carbolactone
    —— (1S, 2R, 4S, 5R)-2-bromo-1,4-di(tert-butyldimethylsilyloxy)-3-oxocyclohexan-1,5-carbolactone 1206715-85-6 C19H35BrO5Si2
    (1S, 2R, 4S, 5R)-2-bromo-1,4-di(tert-butyldimethylsilyloxy)-3-oxocyclohexan-1,5-carbolactone
    —— (1R,3R,4R)-1,4-dihydroxy-5-(thiophen-3-yl)cyclohex-5-ene-1,3-carbolactone 862791-85-3 C11H10O4S
    (1R,3R,4R)-1,4-dihydroxy-5-(thiophen-3-yl)cyclohex-5-ene-1,3-carbolactone
    —— (1R,3R,4R)-1,4-bis(tert-butyldimethylsilyloxy)-5-(thiophen-3-yl)cyclohex-5-ene-1,3-carbolactone 862791-56-8 C23H38O4SSi2
    (1R,3R,4R)-1,4-bis(tert-butyldimethylsilyloxy)-5-(thiophen-3-yl)cyclohex-5-ene-1,3-carbolactone
    —— (4R,5R)-5-((S)-1-Methoxymethoxy-ethyl)-4-methyl-dihydro-furan-2-one 185627-50-3 C9H16O4
    (4R,5R)-5-((S)-1-Methoxymethoxy-ethyl)-4-methyl-dihydro-furan-2-one
    —— (Z)-2-(but-3-enylidene)-4-butanolide 118891-10-4 C8H10O2
    (Z)-2-(but-3-enylidene)-4-butanolide
    —— (E)-2-(but-3-enylidene)-4-butanolide 118891-11-5 C8H10O2
    (E)-2-(but-3-enylidene)-4-butanolide
    —— 6-[2-(4-Hydroxy-phenyl)-ethyl]-tetrahydro-pyran-2-one 850251-77-3 C13H16O3
    6-[2-(4-Hydroxy-phenyl)-ethyl]-tetrahydro-pyran-2-one
    —— (4S,5S)-5-but-3-enyl-4-[tert-butyl(diphenyl)silyl]oxyoxolan-2-one 1110638-60-2 C24H30O3Si
    (4S,5S)-5-but-3-enyl-4-[tert-butyl(diphenyl)silyl]oxyoxolan-2-one
    —— (,Z,Z)-4-(Heptadec-8-enylidene)-3-(hexadec-7-enyl)oxetan-2-one 56000-16-9 C36H64O2
    (,Z,Z)-4-(Heptadec-8-enylidene)-3-(hexadec-7-enyl)oxetan-2-one
    —— epilitsenolide C<sub>1</sub> 111900-41-5 C19H34O3
    epilitsenolide C<sub>1</sub>
    —— (-)-dihydroprotolichesterinic acid 144356-39-8 C19H34O4
    (-)-dihydroprotolichesterinic acid
    —— 5-(hydroxymethyl)-5-pivaloyloxymethyl-3-[(E)-tetradecylidene]tetrahydro-2-furanone 1219016-23-5 C25H44O5
    5-(hydroxymethyl)-5-pivaloyloxymethyl-3-[(E)-tetradecylidene]tetrahydro-2-furanone
    —— (-)-nephromopsinic acid 133695-37-1 C19H34O4
    (-)-nephromopsinic acid
    —— 3-benzyl-3-hydroxydihydrofuran-2-one 905842-21-9 C11H12O3
    3-benzyl-3-hydroxydihydrofuran-2-one
    —— (1S,6S)-9-(Z-bromomethylene)-7-oxabicyclo[4.3.1]dec-2-en-8-one 1358918-65-6 C10H11BrO2
    (1S,6S)-9-(Z-bromomethylene)-7-oxabicyclo[4.3.1]dec-2-en-8-one
    —— 4-Hydroxy-cyclononan-carbonsaeure-(1)-lacton 3041-19-8 C10H16O2
    4-Hydroxy-cyclononan-carbonsaeure-(1)-lacton
    —— (1S,5S,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-2-oxabicyclo[3.2.1]octan-3-one 158469-41-1 C16H30O5Si
    (1S,5S,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-2-oxabicyclo[3.2.1]octan-3-one
    —— (1S,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-2-oxabicyclo[3.2.1]octane-3,4-dione 158469-43-3 C16H28O6Si
    (1S,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-2-oxabicyclo[3.2.1]octane-3,4-dione
    —— (1S,4R,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-2-oxabicyclo[3.2.1]octan-3-one 158469-42-2 C16H30O6Si
    (1S,4R,5R,6S,7R)-7-[tert-butyl(dimethyl)silyl]oxy-6-(dimethoxymethyl)-4-hydroxy-2-oxabicyclo[3.2.1]octan-3-one
    —— (1S,2S,5S,8R)-8,9-seco-8-hydroxy-2-methoxyclovane-9-lactone 1373165-09-3 C16H26O3
    (1S,2S,5S,8R)-8,9-seco-8-hydroxy-2-methoxyclovane-9-lactone
    —— rumphellclovane A 1229351-88-5 C15H24O3
    rumphellclovane A
    —— (+)-(6R,7S)-7-((tert-butyldimethylsilyl)oxy)-2-oxaspiro[5.5]-undec-8-en-1-one 1350558-14-3 C16H28O3Si
    (+)-(6R,7S)-7-((tert-butyldimethylsilyl)oxy)-2-oxaspiro[5.5]-undec-8-en-1-one
    —— (+)-(6R,7S)-7-hydroxy-2-oxaspiro[5.5]undec-8-en-1-one 1350558-13-2 C10H14O3
    (+)-(6R,7S)-7-hydroxy-2-oxaspiro[5.5]undec-8-en-1-one
    —— (3R,5S)-5-((S)-1-Amino-2-cyclohexyl-ethyl)-3-isobutyl-dihydro-furan-2-one 783267-59-4 C16H29NO2
    (3R,5S)-5-((S)-1-Amino-2-cyclohexyl-ethyl)-3-isobutyl-dihydro-furan-2-one