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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
    —— 3β-hydroxy-(2aβ,5aα,8aβ,8bβ)-2a,3,5a,6,7,8,8a,8b-octahydro-6,6,8b-trimethyl-2H-naphtho<1,8-bc>furan-2-one 118916-42-0 C14H20O3
    3β-hydroxy-(2aβ,5aα,8aβ,8bβ)-2a,3,5a,6,7,8,8a,8b-octahydro-6,6,8b-trimethyl-2H-naphtho<1,8-bc>furan-2-one
    —— 3-(1-methylethyl)-5-hydroxy-tetrahydrofuran-2-one 111655-19-7 C7H12O3
    3-(1-methylethyl)-5-hydroxy-tetrahydrofuran-2-one
    —— 5-O-methoxymethylbacillariolide II 203248-47-9 C22H32O4
    5-O-methoxymethylbacillariolide II
    —— 3R,4S-dihydroxy-5S-(1,2,3-trihydroxypropyl)dihydrofuran-2(3H)-one 1561720-89-5 C7H12O7
    3R,4S-dihydroxy-5S-(1,2,3-trihydroxypropyl)dihydrofuran-2(3H)-one
    —— D-Glucoheptonic acid-1,4-lactone 89-67-8 C7H12O7
    D-Glucoheptonic acid-1,4-lactone
    —— (1R,5R)-(-)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane 143169-40-8 C10H14O4
    (1R,5R)-(-)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane
    —— 4,4-dimethyl 5-bromomethyl-γ-butyrolactone 78984-86-8 C7H11BrO2
    4,4-dimethyl 5-bromomethyl-γ-butyrolactone
    —— (4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one 862602-87-7 C22H28O4Si
    (4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one
    —— (4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one 949013-62-1 C22H28O4Si
    (4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one
    —— (2S,2'S,5'R)-5'-((R)-1,2-Dihydroxy-ethyl)-tetrahydro-[2,2']bifuranyl-5-one 749917-41-7 C10H16O5
    (2S,2'S,5'R)-5'-((R)-1,2-Dihydroxy-ethyl)-tetrahydro-[2,2']bifuranyl-5-one
    —— dihydro-4,4,5-trimethyl-2(3H)-furanone 150927-33-6 C7H12O2
    dihydro-4,4,5-trimethyl-2(3H)-furanone
    —— (3S,4S,5R)-4-((1S)-1,2-dihydroxyethyl)-3-methyl-5-tridecyldihydrofuran-2-one 180267-10-1 C20H38O4
    (3S,4S,5R)-4-((1S)-1,2-dihydroxyethyl)-3-methyl-5-tridecyldihydrofuran-2-one
    —— (1R,2R,6R,7R,9S)-<9-exo-cyano-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0<sup>2,6</sup>>dec-4-en-2-endo-yl(1S)-camphanate> 157506-26-8 C24H24N2O6
    (1R,2R,6R,7R,9S)-<9-exo-cyano-4-phenyl-3,10-dioxa-5-azatricyclo<5.2.1.0<sup>2,6</sup>>dec-4-en-2-endo-yl(1S)-camphanate>
    —— (4S,5R,6R)-5-[1,3]Dioxan-2-ylmethyl-6-isopropyl-4-((1E,5Z)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-tetrahydro-pyran-2-one 127891-31-0 C25H44O4Si
    (4S,5R,6R)-5-[1,3]Dioxan-2-ylmethyl-6-isopropyl-4-((1E,5Z)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-tetrahydro-pyran-2-one
    —— (4R,6R)-6-[(1R,6R)-(2E,4E,8E)-9-bromo-1-(tert-butyldimethylsilanyloxy)-6-methoxy-3-methylnona-2,4,8-trienyl]-4-methoxytetrahydropyran-2-one 552849-96-4 C23H39BrO5Si
    (4R,6R)-6-[(1R,6R)-(2E,4E,8E)-9-bromo-1-(tert-butyldimethylsilanyloxy)-6-methoxy-3-methylnona-2,4,8-trienyl]-4-methoxytetrahydropyran-2-one
    —— 4-Hydroxy-cyclooctancarbonsaeurelacton 4744-89-2 C9H14O2
    4-Hydroxy-cyclooctancarbonsaeurelacton
    —— 3-(1-imino-ethyl)-5-methyl-furan-2,4-dione 33488-25-4 C7H9NO3
    3-(1-imino-ethyl)-5-methyl-furan-2,4-dione
    —— (3S,6S)-6-[(1R)-2-triisopropylsilyloxy-1-methylethyl]-3-methyltetrahydro-2H-pyran-2-one 781651-87-4 C18H36O3Si
    (3S,6S)-6-[(1R)-2-triisopropylsilyloxy-1-methylethyl]-3-methyltetrahydro-2H-pyran-2-one
    —— Acetic acid 3-(4-methylene-5-oxo-tetrahydro-furan-2-yl)-propyl ester 104525-99-7 C10H14O4
    Acetic acid 3-(4-methylene-5-oxo-tetrahydro-furan-2-yl)-propyl ester
    —— (+/-)-5-decyn-4-olide 133399-89-0 C10H14O2
    (+/-)-5-decyn-4-olide
    —— 2-Hydroxy-3-cycloheptene-1-acetic acid lactone 75649-70-6 C9H12O2
    2-Hydroxy-3-cycloheptene-1-acetic acid lactone
    —— trans-3-acetyl-4,5-dihydro-4-phenylfuran-2-(3H)-one 71870-65-0 C12H12O3
    trans-3-acetyl-4,5-dihydro-4-phenylfuran-2-(3H)-one
    —— (1R,5S)-1-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl]-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one 1040833-53-1 C26H34O4Si
    (1R,5S)-1-[(1S)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl]-7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-3-one
    —— (R)-tetrahydro-5-oxofuran-2-acetic acid 63597-98-8 C6H8O4
    (R)-tetrahydro-5-oxofuran-2-acetic acid
    —— (5S)-5-[(1S,4S)-6-(tert-butyldimethylsilyloxy)-1-hydroxy-4-methylhexyl]dihydrofuran-2-one 1173997-12-0 C17H34O4Si
    (5S)-5-[(1S,4S)-6-(tert-butyldimethylsilyloxy)-1-hydroxy-4-methylhexyl]dihydrofuran-2-one
    —— 8-oxatricyclo[5.3.1.02,6 ]undecan-9-one 55764-18-6 C10H14O2
    8-oxatricyclo[5.3.1.02,6 ]undecan-9-one
    —— Acetic acid 2,2-dimethyl-4-methylene-5-oxo-tetrahydro-furan-3-yl ester 86289-77-2 C9H12O4
    Acetic acid 2,2-dimethyl-4-methylene-5-oxo-tetrahydro-furan-3-yl ester
    —— Acetic acid 3-methylene-2-oxo-1-oxa-spiro[4.5]dec-4-yl ester 86289-79-4 C12H16O4
    Acetic acid 3-methylene-2-oxo-1-oxa-spiro[4.5]dec-4-yl ester
    —— (R)-6-allyl-5,6-dihydro-3H-pyran-2,4-dione 950513-88-9 C8H10O3
    (R)-6-allyl-5,6-dihydro-3H-pyran-2,4-dione
    —— (1R,2S,5S)-2-Hydroxymethyl-8,8-dimethyl-6-oxa-bicyclo[3.2.1]octan-7-one 866650-89-7 C10H16O3
    (1R,2S,5S)-2-Hydroxymethyl-8,8-dimethyl-6-oxa-bicyclo[3.2.1]octan-7-one
    —— 3-vinyloxetan-2-one 74785-01-6 C5H6O2
    3-vinyloxetan-2-one
    —— (-)-(3R,3aS,9aR)-methyl 2,5-dioxodecahydrocycloocta[b]furan-3-carboxylate 1427029-64-8 C12H16O5
    (-)-(3R,3aS,9aR)-methyl 2,5-dioxodecahydrocycloocta[b]furan-3-carboxylate
    —— (4R,5S)-4-hydroxy-1,7-dioxaspiro[4.4]nonan-8-one 1374115-50-0 C7H10O4
    (4R,5S)-4-hydroxy-1,7-dioxaspiro[4.4]nonan-8-one
    —— (S)-1,7-dioxaspiro[4.4]nonane-4,8-dione 1374115-51-1 C7H8O4
    (S)-1,7-dioxaspiro[4.4]nonane-4,8-dione
    —— bicyclo<2.2.0>hex-5-ene-2,3-dicarboxylic anhydride 68366-13-2 C8H6O3
    bicyclo<2.2.0>hex-5-ene-2,3-dicarboxylic anhydride
    —— chaetomugilin S 1399093-77-6 C23H27ClO6
    chaetomugilin S
    —— dechloro-chaetomugilin D 1399087-20-7 C23H28O6
    dechloro-chaetomugilin D
    —— (S)-7-[2-hydroxyethyl]oxepan-2-one 1018986-39-4 C8H14O3
    (S)-7-[2-hydroxyethyl]oxepan-2-one
    —— 4-Dichloromethylene-tetrahydro-pyran-2-one 190001-90-2 C6H6Cl2O2
    4-Dichloromethylene-tetrahydro-pyran-2-one
    —— (4R,6S)-4-tert-butyldiphenylsilyloxy-6-(hydroxymethyl)tetrahydropyran-2-one 927211-52-7 C22H28O4Si
    (4R,6S)-4-tert-butyldiphenylsilyloxy-6-(hydroxymethyl)tetrahydropyran-2-one
    —— (1R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-8,8-dimethyl-2-methylene-6-oxa-bicyclo[3.2.1]octan-7-one 479541-27-0 C16H28O3Si
    (1R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-8,8-dimethyl-2-methylene-6-oxa-bicyclo[3.2.1]octan-7-one
    —— cis-4-ethyl-3-(trimethylsilyl)-2-oxetanone 67354-22-7 C8H16O2Si
    cis-4-ethyl-3-(trimethylsilyl)-2-oxetanone
    —— trans-4-ethyl-3-(trimethylsilyl)-2-oxetanone 67354-14-7 C8H16O2Si
    trans-4-ethyl-3-(trimethylsilyl)-2-oxetanone
    —— isoambreinolide 18676-08-9 C17H28O2
    isoambreinolide
    —— (3S,4S,5S)-4-ethenyl-2,3,4,5-tetrahydro-3-methyl-5-(14-oxopentadecyl)furan-2-one 501666-54-2 C22H38O3
    (3S,4S,5S)-4-ethenyl-2,3,4,5-tetrahydro-3-methyl-5-(14-oxopentadecyl)furan-2-one
    —— 2-[(2S,3R)-3-ethenyl-2,3,4,5-tetrahydro-5-oxofuran-2-yl]acetic acid 501666-62-2 C8H10O4
    2-[(2S,3R)-3-ethenyl-2,3,4,5-tetrahydro-5-oxofuran-2-yl]acetic acid
    —— 2-methoxycarbonyl-5-[2-methyl-dioxolan-2-yl]-6-oxa-bicyclo[3,2,1]octan-7-one 92237-30-4 C13H18O6
    2-methoxycarbonyl-5-[2-methyl-dioxolan-2-yl]-6-oxa-bicyclo[3,2,1]octan-7-one
    —— (3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one 649755-77-1 C13H26O3Si
    (3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one
    —— 7-methyl-2-oxa-norbornan-3-one 125159-51-5 C7H10O2
    7-methyl-2-oxa-norbornan-3-one
    —— α-Methoxycarbonyl-α-methyl-γ-butyrolacton 41255-44-1 C7H10O4
    α-Methoxycarbonyl-α-methyl-γ-butyrolacton