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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
—— 5-{[tert-Butyl(dimethyl)silyl]oxy}-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde 64091-14-1 C14H24O4Si
5-{[tert-Butyl(dimethyl)silyl]oxy}-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde
—— (4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-bromodihydrofuran-2(3H)-one 142329-74-6 C17H35BrO4Si2
(4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3-bromodihydrofuran-2(3H)-one
—— cis-2-methyl-4-(iodomethyl)-γ-butyrolactone 1729-31-3 C6H9IO2
cis-2-methyl-4-(iodomethyl)-γ-butyrolactone
—— 3-methyl-hexahydro-cyclopenta[<i>b</i>]furan-2-one 40556-75-0 C8H12O2
3-methyl-hexahydro-cyclopenta[<i>b</i>]furan-2-one
—— dihydrodehydroacetic acid methyl ester 116752-23-9 C9H12O4
dihydrodehydroacetic acid methyl ester
—— (3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-2-one 808765-98-2 C14H22O3
(3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-2-one
—— 3-Ethyl-5-hydroxy-3-prop-2-enyloxolan-2-one 80758-92-5 C9H14O3
3-Ethyl-5-hydroxy-3-prop-2-enyloxolan-2-one
—— t-butyl 5-oxo-2-tetrahydrofurancarboxylate 55714-67-5 C9H14O4
t-butyl 5-oxo-2-tetrahydrofurancarboxylate
—— (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester 250225-82-2 C8H12O4
(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester
—— 3-(2-Dimethylaminoethyl)-4,5-dihydro-2(3H)-furanon 88735-21-1 C8H15NO2
3-(2-Dimethylaminoethyl)-4,5-dihydro-2(3H)-furanon
—— 3-(3-Dimethylaminopropyl)-4,5-dihydro-2(3H)-furanon 88735-28-8 C9H17NO2
3-(3-Dimethylaminopropyl)-4,5-dihydro-2(3H)-furanon
—— (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester 13513-80-9 C9H14O4
(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-butyl ester
—— (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-propyl ester 250225-78-6 C8H12O4
(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid n-propyl ester
—— α-ethyl-α-(1,3-dithian-2-ylmethyl)-δ-valerolactone 62937-64-8 C12H20O2S2
α-ethyl-α-(1,3-dithian-2-ylmethyl)-δ-valerolactone
—— 2-[(3Z)-3-ethylidene-2-oxooxan-4-yl]acetic acid 38164-98-6 C9H12O4
2-[(3Z)-3-ethylidene-2-oxooxan-4-yl]acetic acid
—— (3aR,7aS)-2-<(S)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one 134234-25-6 C15H19NO2
(3aR,7aS)-2-<(S)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one
—— (E)-2-(3-ethylidene-2-oxotetrahydro-2H-pyran-4-yl)acetic acid 1160497-80-2 C9H12O4
(E)-2-(3-ethylidene-2-oxotetrahydro-2H-pyran-4-yl)acetic acid
—— (3aS,7aR)-2-<(S)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one 134234-26-7 C15H19NO2
(3aS,7aR)-2-<(S)-1-phenylethyl>-perhydropyrano<3,4-c>pyrrol-4-one
—— 3-cyano-4,6,6-trimethyltetrahydropyranone 87252-19-5 C9H13NO2
3-cyano-4,6,6-trimethyltetrahydropyranone
—— ethyl (E)-4,4-dimethyl-6-oxotetrahydropyran-2-ylideneacetate 85271-77-8 C11H16O4
ethyl (E)-4,4-dimethyl-6-oxotetrahydropyran-2-ylideneacetate
—— Dihydrolitsenolid τ2 38681-12-8 C19H36O3
Dihydrolitsenolid τ2
—— (+)-(3R,4R,5R)-3-tetradecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone 159685-41-3 C19H36O3
(+)-(3R,4R,5R)-3-tetradecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone
—— (1R,4R,5R)-N-hept-6-enyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide 923604-75-5 C14H21NO3
(1R,4R,5R)-N-hept-6-enyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide
—— (4S,6R)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one 1403235-94-8 C10H18O2
(4S,6R)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one
—— β-Pentyl-γ-butyrolacton 55881-98-6 C9H16O2
β-Pentyl-γ-butyrolacton
—— 4,5-dihydro-3,5-dimethyl-3-hydroxy-2(3H)-furanone 86749-58-8 C6H10O3
4,5-dihydro-3,5-dimethyl-3-hydroxy-2(3H)-furanone
—— 3a,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-3,4-dione 79402-15-6 C7H8O3
3a,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-3,4-dione
—— 4-Benzylsulfanyl-3-chloro-5-methoxy-dihydro-furan-2-one 88051-00-7 C12H13ClO3S
4-Benzylsulfanyl-3-chloro-5-methoxy-dihydro-furan-2-one
—— 4-(Benzylsulfanyl)-3-bromo-5-methoxyoxolan-2-one 88050-98-0 C12H13BrO3S
4-(Benzylsulfanyl)-3-bromo-5-methoxyoxolan-2-one
—— 3-Carbomethoxy-5-t-butyldiphenylsilylmethyl tetrahydrofuran-2-one 362610-89-7 C23H28O4Si
3-Carbomethoxy-5-t-butyldiphenylsilylmethyl tetrahydrofuran-2-one
—— (3R)-3-ethyldihydro-5-hydroxy-3-(2-propenyl)-2(3H)-furanone 442632-25-9 C9H14O3
(3R)-3-ethyldihydro-5-hydroxy-3-(2-propenyl)-2(3H)-furanone
—— (3R)-3-ethyldihydro-3-(2-propenyl)-2(3H)-furanone 442632-27-1 C9H14O2
(3R)-3-ethyldihydro-3-(2-propenyl)-2(3H)-furanone
—— 3-Bromo-5-methoxy-4-(pyrrolidin-1-yl)oxolan-2-one 88050-90-2 C9H14BrNO3
3-Bromo-5-methoxy-4-(pyrrolidin-1-yl)oxolan-2-one
—— 3-Chloro-4-isopropylsulfanyl-5-methoxy-dihydro-furan-2-one 88051-01-8 C8H13ClO3S
3-Chloro-4-isopropylsulfanyl-5-methoxy-dihydro-furan-2-one
—— 3-Chloro-4-(diethylamino)-5-methoxyoxolan-2-one 88050-96-8 C9H16ClNO3
3-Chloro-4-(diethylamino)-5-methoxyoxolan-2-one
—— 3-Chloro-5-methoxy-4-(pyrrolidin-1-yl)oxolan-2-one 88050-94-6 C9H14ClNO3
3-Chloro-5-methoxy-4-(pyrrolidin-1-yl)oxolan-2-one
—— 2-Ethyl-5-hydroxyhexanoic acid lactone 26828-95-5 C8H14O2
2-Ethyl-5-hydroxyhexanoic acid lactone
—— (-)-5-methoxycarbonylmethyl-2,,3,4,5-tetrahydrofuran-2-one 63545-49-3 C7H10O4
(-)-5-methoxycarbonylmethyl-2,,3,4,5-tetrahydrofuran-2-one
—— (3aR,4S,6aS)-4-ethenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 84107-60-8 C9H12O2
(3aR,4S,6aS)-4-ethenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
—— α-Tetradecyl-γ-butyrolacton 79102-03-7 C18H34O2
α-Tetradecyl-γ-butyrolacton
—— 3''-Hydroxylovastatin 125638-72-4 C24H36O6
3''-Hydroxylovastatin
—— (S)-5-formyl δ-valerolactone 89408-87-7 C6H8O3
(S)-5-formyl δ-valerolactone
—— (4R,5R)-4-Hydroxy-5-undecyl-4,5-dihydro-2(3H)-furanone 157497-24-0 C15H28O3
(4R,5R)-4-Hydroxy-5-undecyl-4,5-dihydro-2(3H)-furanone
—— 4-n-decyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-80-5 C26H48O2Si
4-n-decyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 5-Ethyl-4-methyl-3-(phenylselanyl)oxolan-2-one 185749-81-9 C13H16O2Se
5-Ethyl-4-methyl-3-(phenylselanyl)oxolan-2-one
—— 4-n-decyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-72-5 C20H36O2Si
4-n-decyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 4-n-decyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-79-2 C26H48O2Si
4-n-decyl-5-methyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— (2S,4R)-(+)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid 88218-39-7 C6H8O4
(2S,4R)-(+)-trans-4-methyl-tetrahydro-5-oxo-2-furancarboxylic acid
—— 4-n-decyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-71-4 C20H36O2Si
4-n-decyl-5-methyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— (2R)-6-oxo-2-undecyloxane-2-carbaldehyde 1024006-23-2 C17H30O3
(2R)-6-oxo-2-undecyloxane-2-carbaldehyde