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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
    —— β-methylene butyrolactone 22195-18-2 C5H6O2
    β-methylene butyrolactone
    —— (8R)-8-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]octahydrooxocin-2-one 1029316-89-9 C11H18O3
    (8R)-8-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]octahydrooxocin-2-one
    —— 4-methyl-2-(1-thiosemicarbazidocarbonyl)-4-pentanolide 479546-53-7 C9H15N3O3S
    4-methyl-2-(1-thiosemicarbazidocarbonyl)-4-pentanolide
    —— (5S)-4,5-dihydro-5-(8-oxotetradecyl)furan-2(3H)-one 928213-29-0 C18H32O3
    (5S)-4,5-dihydro-5-(8-oxotetradecyl)furan-2(3H)-one
    —— (-)-(3R,3aS,8aR)-ethyl 2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate 1427029-72-8 C12H16O5
    (-)-(3R,3aS,8aR)-ethyl 2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate
    —— 5,6-anhydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone 129151-46-8 C6H8O3
    5,6-anhydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone
    —— (+)-(3S,3aR,9aS)-ethyl 2,5-dioxodecahydrocycloocta[b]furan-3-carboxylate 1427029-62-6 C13H18O5
    (+)-(3S,3aR,9aS)-ethyl 2,5-dioxodecahydrocycloocta[b]furan-3-carboxylate
    —— (+)-(3S, 3aR, 8aS)-ethyl 2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate 1427029-74-0 C12H16O5
    (+)-(3S, 3aR, 8aS)-ethyl 2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate
    —— (+)-(3S, 3aR, 7R, 8aS)-ethyl 7-(tert-butyldimethylsilyloxy)-2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate 1427029-78-4 C18H30O6Si
    (+)-(3S, 3aR, 7R, 8aS)-ethyl 7-(tert-butyldimethylsilyloxy)-2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate
    —— (-)-(3S,3aS,8aR)-3-methylhexahydro-2H-cyclohepta[b]furan-2,5(3H)-dione 1427029-88-6 C10H14O3
    (-)-(3S,3aS,8aR)-3-methylhexahydro-2H-cyclohepta[b]furan-2,5(3H)-dione
    —— (+)-(3R,3aR,9aS)-3-methylhexahydrocycloocta[b]furan-2,5-(3H,6H)-dione 1427029-84-2 C11H16O3
    (+)-(3R,3aR,9aS)-3-methylhexahydrocycloocta[b]furan-2,5-(3H,6H)-dione
    —— (+/-)-ethyl 2,5-dioxoperhydrocycloocta[b]furan-3-carboxylate —— C13H18O5
    (+/-)-ethyl 2,5-dioxoperhydrocycloocta[b]furan-3-carboxylate
    —— (+/-)-(3R,3aS,7S,8aR)-ethyl 7-(tert-butyldimethylsilyloxy)-2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate —— C18H30O6Si
    (+/-)-(3R,3aS,7S,8aR)-ethyl 7-(tert-butyldimethylsilyloxy)-2,5-dioxooctahydro-2H-cyclohepta[b]furan-3-carboxylate
    —— 4-oxabicyclo[3.2.1]oct-6-en-3-one 5650-65-7 C7H8O2
    4-oxabicyclo[3.2.1]oct-6-en-3-one
    —— (1S,2S)-2-((R)-8-oxooxocan-2-yl)cyclopropanecarbaldehyde 1293981-62-0 C11H16O3
    (1S,2S)-2-((R)-8-oxooxocan-2-yl)cyclopropanecarbaldehyde
    —— (8R)-8-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]octahydrooxocin-2-one 1029316-90-2 C11H16O3
    (8R)-8-[(1R,2R)-2-(hydroxymethyl)cyclopropyl]octahydrooxocin-2-one
    —— (4R,5R,8R)-5,8-oxido-12-oxotricosan-1,4-olide 303053-01-2 C12H18O4
    (4R,5R,8R)-5,8-oxido-12-oxotricosan-1,4-olide
    —— 3-(5-oxo-tetrahydro-furan-3-yl)-propionic acid 81203-31-8 C7H10O4
    3-(5-oxo-tetrahydro-furan-3-yl)-propionic acid
    —— (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5S)-5-[(2S,5S)-5-[(2R)-5-oxooxolan-2-yl]oxolan-2-yl]oxolan-2-yl]butanal 862557-91-3 C22H38O6Si
    (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2R,5S)-5-[(2S,5S)-5-[(2R)-5-oxooxolan-2-yl]oxolan-2-yl]oxolan-2-yl]butanal
    —— Hfdsmbuicgaqep-ilmpwqcysa- 99457-92-8 C20H30O4
    Hfdsmbuicgaqep-ilmpwqcysa-
    —— (R)-6-(t-butyldiphenylsiloxymethyl)-6-undecyltetrahydropyran-2-one 755016-02-5 C33H50O3Si
    (R)-6-(t-butyldiphenylsiloxymethyl)-6-undecyltetrahydropyran-2-one
    —— 4,6-Dimethoxyhexahydrocyclobuta[1,2-c:3,4-c']difuran-1,3-dione 53042-83-4 C10H12O6
    4,6-Dimethoxyhexahydrocyclobuta[1,2-c:3,4-c']difuran-1,3-dione
    —— (1R,3R,5R,8S,9S)-3,5-dimethyl-2,6-dioxatricyclo[6.5.0.01,9]tridecan-7-one 189636-77-9 C13H20O3
    (1R,3R,5R,8S,9S)-3,5-dimethyl-2,6-dioxatricyclo[6.5.0.01,9]tridecan-7-one
    —— cis-4-Methyl-6-(2-methylpropyl)-3,4,5,6-tetrahydro-2H-pyran-2-on 14983-21-2 C10H18O2
    cis-4-Methyl-6-(2-methylpropyl)-3,4,5,6-tetrahydro-2H-pyran-2-on
    —— 4,5-dihydro-5-(hydroxymethyl)-3-methylene-2(3H)-furanone 82112-63-8 C6H8O3
    4,5-dihydro-5-(hydroxymethyl)-3-methylene-2(3H)-furanone
    —— (S)-5-(hydroxymethyl)-3-methylenedihydrofuran-2(3H)-one 216868-51-8 C6H8O3
    (S)-5-(hydroxymethyl)-3-methylenedihydrofuran-2(3H)-one
    —— 4-methyl-hexahydro-cyclopenta[<i>b</i>]pyran-2-one 91005-30-0 C9H14O2
    4-methyl-hexahydro-cyclopenta[<i>b</i>]pyran-2-one
    —— (3S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyldihydrofuran-2(3H)-one 133329-79-0 C12H24O3Si
    (3S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyldihydrofuran-2(3H)-one
    —— (4S)-4-(dimethoxymethyl)butano-4-lactone 731862-45-6 C7H12O4
    (4S)-4-(dimethoxymethyl)butano-4-lactone
    —— (5S)-5-({[Tri(propan-2-yl)silyl]oxy}methyl)oxolan-2-one 189516-38-9 C14H28O3Si
    (5S)-5-({[Tri(propan-2-yl)silyl]oxy}methyl)oxolan-2-one
    —— (2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-γ-butyrolactone 133329-79-0 C12H24O3Si
    (2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-γ-butyrolactone
    —— (+)-(R)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one 138298-25-6 C13H16O2
    (+)-(R)-5-(3-phenylpropyl)dihydrofuran-2(3H)-one
    —— (S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran 24211-53-8 C5H7N3O2
    (S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran
    —— (3R,5S)-5-(bromomethyl)-3-propyloxolan-2-one 193266-45-4 C8H13BrO2
    (3R,5S)-5-(bromomethyl)-3-propyloxolan-2-one
    —— (3R,5S)-5-(hydroxymethyl)-3-propyloxolan-2-one 193266-44-3 C8H14O3
    (3R,5S)-5-(hydroxymethyl)-3-propyloxolan-2-one
    —— (S)-γ-Phenylselenomethyl-γ-butyrolactone 93752-75-1 C11H12O2Se
    (S)-γ-Phenylselenomethyl-γ-butyrolactone
    —— (5S)-5-(chloromethyl)oxolan-2-one 179797-19-4 C5H7ClO2
    (5S)-5-(chloromethyl)oxolan-2-one
    —— (5S)-(allyldimethylsilyloxymethyl)-tetrahydrofuran-2-one 322400-13-5 C10H18O3Si
    (5S)-(allyldimethylsilyloxymethyl)-tetrahydrofuran-2-one
    —— (3R,5S)-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-3-<2-methylene-3-(tetrahydropyran-2-yloxy)propyl>-2(3H)-furanone 159691-84-6 C30H40O5Si
    (3R,5S)-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-3-<2-methylene-3-(tetrahydropyran-2-yloxy)propyl>-2(3H)-furanone
    —— (3R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-fluoro-3-methyldihydrofuran-2(3H)-one 1417797-17-1 C22H27FO3Si
    (3R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-fluoro-3-methyldihydrofuran-2(3H)-one
    —— (1R,2S,5R,6R,7S)-5-butyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 528609-86-1 C19H22O2
    (1R,2S,5R,6R,7S)-5-butyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
    —— 3R,5S-5-mesyloxymethyl-3-methyl-4,5-dihydro-2(3H)-furanone 147093-39-8 C7H12O5S
    3R,5S-5-mesyloxymethyl-3-methyl-4,5-dihydro-2(3H)-furanone
    —— (3S,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone 159691-86-8 C25H31BrO3Si
    (3S,5S)-3-(3-bromo-2-methylenepropyl)-5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone
    —— (1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-isopropyl-6,8-naphthalenecarbolactone 1026534-21-3 C17H24O4
    (1S,2S,4aR,6S,8S,8aS)-1-(ethoxycarbonyl)-1,2,4a,5,6,7,8,8a-octahydro-2-isopropyl-6,8-naphthalenecarbolactone
    —— (3'R,3''S,5'S,5''S)-3',3''-(2-methylene-1,3-propanediyl)bis<5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone> 159691-87-9 C46H56O6Si2
    (3'R,3''S,5'S,5''S)-3',3''-(2-methylene-1,3-propanediyl)bis<5-<(tert-butyldiphenylsilyloxy)methyl>-4,5-dihydro-2(3H)-furanone>
    —— (1R,2S,5S,6R,7S)-5-butyl-5-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 528609-83-8 C14H20O2
    (1R,2S,5S,6R,7S)-5-butyl-5-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
    —— (1R,2S,5R,6R,7S)-5-methyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 528609-84-9 C16H16O2
    (1R,2S,5R,6R,7S)-5-methyl-5-phenyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
    —— tert-butyl N-[(2S)-1-[(1S,2S)-2-[[(2R,3S)-3-[(2S)-butan-2-yl]-4-oxooxetane-2-carbonyl]amino]cyclopropyl]but-3-en-2-yl]carbamate 1431768-70-5 C20H32N2O5
    tert-butyl N-[(2S)-1-[(1S,2S)-2-[[(2R,3S)-3-[(2S)-butan-2-yl]-4-oxooxetane-2-carbonyl]amino]cyclopropyl]but-3-en-2-yl]carbamate
    —— (1R,2S,5S,6R,7S)-5-allyl-5-methyl-4-oxatricyclo[5.2.1.0<sup>2,6</sup>]dec-8-en-3-one 654676-15-0 C13H16O2
    (1R,2S,5S,6R,7S)-5-allyl-5-methyl-4-oxatricyclo[5.2.1.0<sup>2,6</sup>]dec-8-en-3-one
    —— (3S,5S)-3-<2'(E),4'(E)-6-methylheptadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one 1026414-32-3 C29H38O3Si
    (3S,5S)-3-<2'(E),4'(E)-6-methylheptadienyl>-5-((tert-butyldiphenylsiloxy)methyl)tetrahydrofuran-2-one