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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-hydroxymethyl-5-octadecyloxymethyl-4,5-dihydro-2(3H)furanone 108225-28-1 C24H46O4
5-hydroxymethyl-5-octadecyloxymethyl-4,5-dihydro-2(3H)furanone
—— (+/-)-4-Methyl-2,4-dihydroxypentansaeure 1-> 4 Lacton 72496-35-6 C6H10O3
(+/-)-4-Methyl-2,4-dihydroxypentansaeure 1-> 4 Lacton
—— (1S,2R,6S,9R)-(-)-7-oxatricyclo[4.3.0.0<sup>2,9</sup>]nonan-8-one 172722-65-5 C8H10O2
(1S,2R,6S,9R)-(-)-7-oxatricyclo[4.3.0.0<sup>2,9</sup>]nonan-8-one
—— cycloheptyl-5 pentanolide-4 96009-80-2 C12H20O2
cycloheptyl-5 pentanolide-4
—— 5'-Methyl-3,4-dihydro-2H-[2,2']bifuranyl-5-one 116118-71-9 C9H10O3
5'-Methyl-3,4-dihydro-2H-[2,2']bifuranyl-5-one
—— 3-Ethyl-5-(prop-2-ynoxymethyl)oxolan-2-one 116214-72-3 C10H14O3
3-Ethyl-5-(prop-2-ynoxymethyl)oxolan-2-one
—— (1R,5S)-1-[1-tri(isopropyl)silanyloxy-vinyl]-3-oxa-bicyclo[3.1.0]hexan-2-one 860480-92-8 C16H28O3Si
(1R,5S)-1-[1-tri(isopropyl)silanyloxy-vinyl]-3-oxa-bicyclo[3.1.0]hexan-2-one
—— 6-(2-Chloro-ethyl)-tetrahydro-pyran-2-one 111711-03-6 C7H11ClO2
6-(2-Chloro-ethyl)-tetrahydro-pyran-2-one
—— [(S)-2-Cyclohexyl-1-((2R,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester 124032-44-6 C20H35NO4
[(S)-2-Cyclohexyl-1-((2R,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester
—— 4-Cyclohexylidene-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 116239-70-4 C13H16O2
4-Cyclohexylidene-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
—— 5,5-Dimethyl-4-methylideneoxolan-2-one 132994-88-8 C7H10O2
5,5-Dimethyl-4-methylideneoxolan-2-one
—— 4,5-dihydro-4-methyl-5-phenyl-2(3H)-furanone 20568-06-3 C11H12O2
4,5-dihydro-4-methyl-5-phenyl-2(3H)-furanone
—— 3-Methyl-3,3a,4,5-tetrahydro-cyclopenta[c]furan-1-one 115399-35-4 C8H10O2
3-Methyl-3,3a,4,5-tetrahydro-cyclopenta[c]furan-1-one
—— (R)-5-formyl δ-valerolactone 160154-84-7 C6H8O3
(R)-5-formyl δ-valerolactone
—— 5(R)-5-<1(S)-1-(N-Boc-amino)-3-methylbutyl>dihydrofuran-2(3H)-one 105018-83-5 C14H25NO4
5(R)-5-<1(S)-1-(N-Boc-amino)-3-methylbutyl>dihydrofuran-2(3H)-one
—— exo-4-hydroxy-6-oxabicyclo<3.2.1>oct-2-en-7-one —— C7H8O3
exo-4-hydroxy-6-oxabicyclo<3.2.1>oct-2-en-7-one
—— 3Beta-Hydroxy Pravastatin Lactone (>90%) 87984-67-6 C23H34O6
3Beta-Hydroxy Pravastatin Lactone (>90%)
—— (6R)-6-<(1S)-1-(tert-butoxycarbonylamino)ethyl>-5,6-dihydro-2H-pyran-2,4(3H)-dione 119960-14-4 C12H19NO5
(6R)-6-<(1S)-1-(tert-butoxycarbonylamino)ethyl>-5,6-dihydro-2H-pyran-2,4(3H)-dione
—— 4-allyltetrahydro-2H-pyran-2-one 214335-81-6 C8H12O2
4-allyltetrahydro-2H-pyran-2-one
—— (S)-3-methylene-5-phenethyl-tetrahydro-furan-2-one 1159115-00-0 C13H14O2
(S)-3-methylene-5-phenethyl-tetrahydro-furan-2-one
—— (R)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methylene-tetrahydro-furan-2-one 1159115-01-1 C23H28O3Si
(R)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methylene-tetrahydro-furan-2-one
—— α-(4,4-dimethylcyclohex-1-enyl)-γ-butyrolactone 89908-80-5 C12H18O2
α-(4,4-dimethylcyclohex-1-enyl)-γ-butyrolactone
—— (3AR,6AS)-3,3,5,5-Tetramethylhexahydro-1H-cyclopenta[C]furan-1-one 79618-64-7 C11H18O2
(3AR,6AS)-3,3,5,5-Tetramethylhexahydro-1H-cyclopenta[C]furan-1-one
—— 1,3-dimethyl-8-oxabicyclo-<5.3.0>-dec-3-en-2,9-dione 121878-54-4 C11H14O3
1,3-dimethyl-8-oxabicyclo-<5.3.0>-dec-3-en-2,9-dione
—— α-(diethoxyphosphinyl)-δ-valerolactone 122593-65-1 C9H17O5P
α-(diethoxyphosphinyl)-δ-valerolactone
—— (3S,4S,5R,6R)-3,4-dihydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one 765941-82-0 C12H9F5O4
(3S,4S,5R,6R)-3,4-dihydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one
—— (3S,4S,6R)-3,4-dihydroxy-6-pentafluorophenyltetrahydropyran-2-one 765941-80-8 C11H7F5O4
(3S,4S,6R)-3,4-dihydroxy-6-pentafluorophenyltetrahydropyran-2-one
—— (3S,4S,5S,6R)-3,4-dihydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one 765941-81-9 C12H9F5O4
(3S,4S,5S,6R)-3,4-dihydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one
—— (1S,5S)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane 143169-41-9 C10H14O4
(1S,5S)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane
—— 4,5-dihydro-3-methylene-5-octyl-2(3H)-furanone 65652-00-8 C13H22O2
4,5-dihydro-3-methylene-5-octyl-2(3H)-furanone
—— tricyclo<2<sup>3,6</sup>.1.1.0>pyran-2-one 19192-82-6 C5H4O2
tricyclo<2<sup>3,6</sup>.1.1.0>pyran-2-one
—— α-methylene-γ-nonalactone 83650-09-3 C10H16O2
α-methylene-γ-nonalactone
—— (4-methylen-5-oxotetrahydrofuran-2-yl)methyl acetate 1254693-06-5 C8H10O4
(4-methylen-5-oxotetrahydrofuran-2-yl)methyl acetate
—— 4-(hydroxymethyl)-4-methyl-2-methylenebutanolide 118171-01-0 C7H10O3
4-(hydroxymethyl)-4-methyl-2-methylenebutanolide
—— (5S,4'S,5'R)-5-<3'-<(tert-butyloxy)carbonyl>-4'-(cyclohexylmethyl)-2',2'-dimethyloxazolidin-5'-yl>-3-methylenedihydrofuran-2(4H)-one 122226-02-2 C22H35NO5
(5S,4'S,5'R)-5-<3'-<(tert-butyloxy)carbonyl>-4'-(cyclohexylmethyl)-2',2'-dimethyloxazolidin-5'-yl>-3-methylenedihydrofuran-2(4H)-one
—— (+)-(3S,5R)-3-hydroxy-5-decanolide 111688-88-1 C10H18O3
(+)-(3S,5R)-3-hydroxy-5-decanolide
—— (5R)-5-[(1R)-1-hydroxy-2-propenyl]dihydro-2(3H)furanone 608531-99-3 C7H10O3
(5R)-5-[(1R)-1-hydroxy-2-propenyl]dihydro-2(3H)furanone
—— (methyl-3 butyl)-2 γ-valerolactone 40923-62-4 C10H18O2
(methyl-3 butyl)-2 γ-valerolactone
—— (1S,4R)-(-)-ethylcamphamide 85805-97-6 C12H19NO3
(1S,4R)-(-)-ethylcamphamide
—— 6-hydroxy-1-oxaspiro[4.5]decan-2-one —— C9H14O3
6-hydroxy-1-oxaspiro[4.5]decan-2-one
—— Lacton der cis-2-(2-Hydroxy-3-methyl-cyclopentyl)-propionsaeure 1196-16-3 C9H14O2
Lacton der cis-2-(2-Hydroxy-3-methyl-cyclopentyl)-propionsaeure
—— (3R,4R)-3-methyl-4-ethyloxetan-2-one 1057557-67-1 C6H10O2
(3R,4R)-3-methyl-4-ethyloxetan-2-one
—— 4a-Ethyl-7-hydroxyhexahydrocyclopenta[b]pyran-2(3H)-one 103252-48-8 C10H16O3
4a-Ethyl-7-hydroxyhexahydrocyclopenta[b]pyran-2(3H)-one
—— α-Methoxy-γ-valerolacton 89489-71-4 C6H10O3
α-Methoxy-γ-valerolacton
—— 5-O-(tert-butyldimethylsilyl)-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone 128685-02-9 C15H26O5Si
5-O-(tert-butyldimethylsilyl)-2,3,7,8-tetradeoxy-L-glycero-L-manno-nonaric acid di-γ-lactone
—— 3-(2-Methylbutyl)oxolan-2-one 112936-65-9 C9H16O2
3-(2-Methylbutyl)oxolan-2-one
—— (3aR,4S,7R,7aS)-7a-[(S)-1-hydroxy-2-methylpropyl]-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one 1432904-77-2 C14H20O3
(3aR,4S,7R,7aS)-7a-[(S)-1-hydroxy-2-methylpropyl]-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one
—— (3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one —— C10H12O2
(3aRS,4SR,7RS,7aSR)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one
—— 3-oxabicyclo<3.1.1>heptan-2-one-1-carboxylic acid 17160-65-5 C7H8O4
3-oxabicyclo<3.1.1>heptan-2-one-1-carboxylic acid
—— 3-pentadecylglutaric anhydride 1314643-24-7 C20H36O3
3-pentadecylglutaric anhydride