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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
    —— (4S,5R)-dihydro-5-hydroxymethyl-4-methyl-2(3H)-furanone 73991-99-8 C6H10O3
    (4S,5R)-dihydro-5-hydroxymethyl-4-methyl-2(3H)-furanone
    —— methyl-4-trichloromethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 72296-75-4 C10H11Cl3O4
    methyl-4-trichloromethyl-6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate
    —— (3aS,6R,6aR)-6a-[(1,3-dioxolan-2-yl)methyl]-3,3,6-trimethylhexahydro-1H-cyclopenta[c]furan-1-one 1335003-42-3 C14H22O4
    (3aS,6R,6aR)-6a-[(1,3-dioxolan-2-yl)methyl]-3,3,6-trimethylhexahydro-1H-cyclopenta[c]furan-1-one
    —— (E)-(3S)-6-O-decyl-2,3-dideoxy-3-(oct-1-enyl)-D-threo-hexono-1,4-lactone 1092810-65-5 C24H44O4
    (E)-(3S)-6-O-decyl-2,3-dideoxy-3-(oct-1-enyl)-D-threo-hexono-1,4-lactone
    —— (4R,5S)-trans-crobarbatic acid —— C7H10O4
    (4R,5S)-trans-crobarbatic acid
    —— 4-(4-chlorophenyl)tetrahydro-2H-pyran-2-one 183504-77-0 C11H11ClO2
    4-(4-chlorophenyl)tetrahydro-2H-pyran-2-one
    —— (3S,5S)-3-(tert-butyldimethylsilyloxy)-5-vinyldihydrofuran-2(3H)-one 1335208-13-3 C12H22O3Si
    (3S,5S)-3-(tert-butyldimethylsilyloxy)-5-vinyldihydrofuran-2(3H)-one
    —— [5,5-2H2]mevalonic acid lactone 6158-93-6 C6H10O3
    [5,5-2H2]mevalonic acid lactone
    —— cis-(RS,SR)-γ-(1-cyclohexen-1-yl)-γ-hydroxy-β-methylbutanoic acid lactone 133101-55-0 C11H16O2
    cis-(RS,SR)-γ-(1-cyclohexen-1-yl)-γ-hydroxy-β-methylbutanoic acid lactone
    —— cryptocaryolone 163860-37-5 C12H20O5
    cryptocaryolone
    —— 6-(3-hydroxy-3-oxopropyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 156806-20-1 C8H12O4
    6-(3-hydroxy-3-oxopropyl)-3,4,5,6-tetrahydro-2H-pyran-2-one
    —— (1S,5R)-2-oxo-1-(4-fluorophenyl)-3-oxabicyclo[3.1.0]hexane 528587-71-5 C11H9FO2
    (1S,5R)-2-oxo-1-(4-fluorophenyl)-3-oxabicyclo[3.1.0]hexane
    —— (1R,5S)-2-oxo-1-(4-fluorophenyl)-3-oxabicyclo[3.1.0]hexane 942493-37-0 C11H9FO2
    (1R,5S)-2-oxo-1-(4-fluorophenyl)-3-oxabicyclo[3.1.0]hexane
    —— (+)-Epiverrucarinolactone 88196-10-5 C6H10O3
    (+)-Epiverrucarinolactone
    —— (1R,5S,6S,7S)-7-tert-butyldiphenylsilyloxy-6-hydroxymethyl-2-oxabicyclo<3.3.0>octan-3-one 160998-94-7 C24H30O4Si
    (1R,5S,6S,7S)-7-tert-butyldiphenylsilyloxy-6-hydroxymethyl-2-oxabicyclo<3.3.0>octan-3-one
    —— (4R,5S)-3-[(E)-2-hexynylidene-4-hydroxy-5-methyltetrahydro-2-furanone] 305817-94-1 C11H14O3
    (4R,5S)-3-[(E)-2-hexynylidene-4-hydroxy-5-methyltetrahydro-2-furanone]
    —— (2S,4S)-tetrahydro-4-isopropyl-5-oxofuran-2-carbonitrile 1165874-77-0 C8H11NO2
    (2S,4S)-tetrahydro-4-isopropyl-5-oxofuran-2-carbonitrile
    —— (3R)-3-isopropyl-5-(nitromethyl)dihydrofuran-2(3H)-one 1165874-86-1 C8H13NO4
    (3R)-3-isopropyl-5-(nitromethyl)dihydrofuran-2(3H)-one
    —— 8-hydroxy-2-oxa-spiro[4.5]decan-1-one 67132-92-7 C9H14O3
    8-hydroxy-2-oxa-spiro[4.5]decan-1-one
    —— 5,5-Dimethyl-dihydro-pyran-2,4-dione 874097-49-1 C7H10O3
    5,5-Dimethyl-dihydro-pyran-2,4-dione
    —— 4,5-dihydro-5-(2-mercaptoethyl)-2(3H)-furanone 80901-14-0 C6H10O2S
    4,5-dihydro-5-(2-mercaptoethyl)-2(3H)-furanone
    —— 4-tert.-Butyl-cyclohexan-diessigsaeure-(1,1)-anhydrid 93807-74-0 C14H22O3
    4-tert.-Butyl-cyclohexan-diessigsaeure-(1,1)-anhydrid
    —— Ethyl 2-hydroxy-2-(2-oxooxan-3-ylidene)acetate 110977-72-5 C9H12O5
    Ethyl 2-hydroxy-2-(2-oxooxan-3-ylidene)acetate
    —— (1R,2S,6S,8S)-3,6-dimethoxy-4,9-dioxatricyclo[6.3.0.02,6]undecan-10-one 104620-80-6 C11H16O5
    (1R,2S,6S,8S)-3,6-dimethoxy-4,9-dioxatricyclo[6.3.0.02,6]undecan-10-one
    —— 7-oxabicyclo[4.2.2]dec-4-en-8-one 71404-72-3 C9H12O2
    7-oxabicyclo[4.2.2]dec-4-en-8-one
    —— (6S,4R)-6-(tert-butyldiphenylsilanyloxymethyl)-4-vinyltetrahydropyran-2-one 404338-82-5 C24H30O3Si
    (6S,4R)-6-(tert-butyldiphenylsilanyloxymethyl)-4-vinyltetrahydropyran-2-one
    —— cis-9a-(2-Hexynyl)octahydrocycloocta<c>furan-1(3H)-one 130082-84-7 C16H24O2
    cis-9a-(2-Hexynyl)octahydrocycloocta<c>furan-1(3H)-one
    —— cis-8a-(2-Hexynyl)octahydro-1H-cyclohepta<c>furan-1-one 130082-83-6 C15H22O2
    cis-8a-(2-Hexynyl)octahydro-1H-cyclohepta<c>furan-1-one
    —— (1'R,2'S,4S,6'S,8'R,11'S,15'R)-15'-(2-chloroethyl)-2,2,4',4'-tetramethylspiro[1,3-dioxolane-4,7'-3,5,9,12-tetraoxa-14-azatetracyclo[6.6.1.01,11.02,6]pentadecane]-10',13'-dione 616225-51-5 C18H24ClNO8
    (1'R,2'S,4S,6'S,8'R,11'S,15'R)-15'-(2-chloroethyl)-2,2,4',4'-tetramethylspiro[1,3-dioxolane-4,7'-3,5,9,12-tetraoxa-14-azatetracyclo[6.6.1.01,11.02,6]pentadecane]-10',13'-dione
    —— (3aS,5S,6aS)-(-)-5-(Methylsufonyloxy)-6a-methyl-hexahydro-2H-cyclopenta<b>furan-2-on 154603-31-3 C9H14O5S
    (3aS,5S,6aS)-(-)-5-(Methylsufonyloxy)-6a-methyl-hexahydro-2H-cyclopenta<b>furan-2-on
    —— (1S,2R,3S,5R,6R,7R,8S,9S,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one 2571-22-4 C15H18O6
    (1S,2R,3S,5R,6R,7R,8S,9S,12R)-2,8-dihydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
    —— (4aR,5R,7R,8aS)-7-methyl-5-phenyl-4,4a,5,7,8,8a-hexahydro-3H-pyrano[3,2-c]pyran-2-one 1025740-30-0 C15H18O3
    (4aR,5R,7R,8aS)-7-methyl-5-phenyl-4,4a,5,7,8,8a-hexahydro-3H-pyrano[3,2-c]pyran-2-one
    —— (R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)dihydrofuran-2(3H)-one 1416253-45-6 C10H18O4
    (R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)dihydrofuran-2(3H)-one
    —— tert-butyl (4-hydroxy-4-methyl-1-(2-oxodihydrofuran-3-ylidene)pentan-2-yl)carbamate 1416253-40-1 C15H25NO5
    tert-butyl (4-hydroxy-4-methyl-1-(2-oxodihydrofuran-3-ylidene)pentan-2-yl)carbamate
    —— 6-(bromomethyl)-4,6-diphenyltetrahydro-2H-pyran-2-one 1433223-50-7 C18H16BrClO2
    6-(bromomethyl)-4,6-diphenyltetrahydro-2H-pyran-2-one
    —— 3-benzylidene-2-oxo-4-butanolide 106203-51-4 C11H8O3
    3-benzylidene-2-oxo-4-butanolide
    —— 2-(furan-2-yl)dihydro-2H-pyran-2,6(3H)dione 1268140-00-6 C9H8O4
    2-(furan-2-yl)dihydro-2H-pyran-2,6(3H)dione
    —— (3R,5R)-5-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-3-methyloxolan-2-one 1231765-64-2 C15H30O3Si
    (3R,5R)-5-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-3-methyloxolan-2-one
    —— (5R)-5-[4-[tert-butyl(dimethyl)silyl]oxybutyl]oxolan-2-one 1231765-63-1 C14H28O3Si
    (5R)-5-[4-[tert-butyl(dimethyl)silyl]oxybutyl]oxolan-2-one
    —— (+)-dubiusamine A 1231900-72-3 C18H31NO4
    (+)-dubiusamine A
    —— dihydro-3-trimethylsiloxy-4,4-dimethylfuran-2(3H)-one 56193-78-3 C9H18O3Si
    dihydro-3-trimethylsiloxy-4,4-dimethylfuran-2(3H)-one
    —— 3-chloro-4,4-dimethyl-dihydro-furan-2-one 42411-53-0 C6H9ClO2
    3-chloro-4,4-dimethyl-dihydro-furan-2-one
    —— pantolactone methoxymethyl ether 90113-81-8 C8H14O4
    pantolactone methoxymethyl ether
    —— acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 84822-49-1 C9H12O4
    acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester
    —— cephalosporolide D 365219-46-1 C8H14O3
    cephalosporolide D
    —— 3-Allyl-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 231632-35-2 C10H12O2
    3-Allyl-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
    —— trans-3-methylene-4-methyl-5-phenyltetrahydrofuran-2-one 103547-98-4 C12H12O2
    trans-3-methylene-4-methyl-5-phenyltetrahydrofuran-2-one
    —— α-methylene β-methyl γ-phenyl γ-butyrolactone 119105-35-0 C12H12O2
    α-methylene β-methyl γ-phenyl γ-butyrolactone
    —— (-)(2S,3R)-cyclosarkomycin 82093-34-3 C7H8O3
    (-)(2S,3R)-cyclosarkomycin
    —— methyl (3aS,5S,6aR)-5-[tert-butyl(dimethyl)silyl]oxy-3-oxo-4,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-3a-carboxylate 184376-32-7 C15H26O5Si
    methyl (3aS,5S,6aR)-5-[tert-butyl(dimethyl)silyl]oxy-3-oxo-4,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-3a-carboxylate