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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
—— (R,Z)-3-butyl-4-pentylideneoxetan-2-one 898799-30-9 C12H20O2
(R,Z)-3-butyl-4-pentylideneoxetan-2-one
—— (E)-3-butyl-4-pentylideneoxetan-2-one 872631-12-4 C12H20O2
(E)-3-butyl-4-pentylideneoxetan-2-one
—— 3β,3aβ,6α,6aβ-Nepetolactone 58845-57-1 C9H14O2
3β,3aβ,6α,6aβ-Nepetolactone
—— 3α,3aβ,6α,6aβ-Nepetolactone 58845-58-2 C9H14O2
3α,3aβ,6α,6aβ-Nepetolactone
—— 4,7-Methano-1,3-dioxolo(4,5-c)oxepin-6(4H)-one, tetrahydro-2,2-dimethyl- 4420-12-6 C10H14O4
4,7-Methano-1,3-dioxolo(4,5-c)oxepin-6(4H)-one, tetrahydro-2,2-dimethyl-
—— 4-chloro-5-ethyldihydrofuran-2(3H)-one 139086-12-7 C6H9ClO2
4-chloro-5-ethyldihydrofuran-2(3H)-one
—— 5'-Chloromethyl-5'-hydroxy-2-methyl-tetrahydro-[2,2']bifuranyl-5-one 85263-94-1 C10H15ClO4
5'-Chloromethyl-5'-hydroxy-2-methyl-tetrahydro-[2,2']bifuranyl-5-one
—— 2-<1-Hydroxy-ethyl>-cyclobutan-1-carbonsaeure-lacton 2983-99-5 C7H10O2
2-<1-Hydroxy-ethyl>-cyclobutan-1-carbonsaeure-lacton
—— 3-Methyl-3-((E)-2-nitro-vinyl)-tetrahydro-pyran-2-one 114577-86-5 C8H11NO4
3-Methyl-3-((E)-2-nitro-vinyl)-tetrahydro-pyran-2-one
—— (S)-3-Methyl-3-((E)-2-nitro-propenyl)-tetrahydro-pyran-2-one 102631-78-7 C9H13NO4
(S)-3-Methyl-3-((E)-2-nitro-propenyl)-tetrahydro-pyran-2-one
—— (+)-megislactone 1033128-17-4 C31H58O3
(+)-megislactone
—— (4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-hexahydro-6-tert-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-tert-butyldimethylsilyloxy-2H-pyran-2-one 159225-69-1 C30H54O5Si2
(4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-hexahydro-6-tert-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-tert-butyldimethylsilyloxy-2H-pyran-2-one
—— tert-butyl [(1R,3R,4R,5R)-4-bromo-7-oxo-6-oxabicyclo-[3.2.0]hept-3-yl]carbamate 1113025-57-2 C11H16BrNO4
tert-butyl [(1R,3R,4R,5R)-4-bromo-7-oxo-6-oxabicyclo-[3.2.0]hept-3-yl]carbamate
—— (+)-(3R,5R)-3-(tert-butyldiphenylsilyloxy)-5-hexanolide 263369-05-7 C22H28O3Si
(+)-(3R,5R)-3-(tert-butyldiphenylsilyloxy)-5-hexanolide
—— 5-methyl-3-oxa-bicyclo[3.1.0]hexan-2-one 35589-61-8 C6H8O2
5-methyl-3-oxa-bicyclo[3.1.0]hexan-2-one
—— (+)-(2S,3R,5R)-2,3-dihydroxy-5-hexanolide 263369-04-6 C6H10O4
(+)-(2S,3R,5R)-2,3-dihydroxy-5-hexanolide
—— 1β,10β-Epoxy-3-oxo-8β-isobutyroxy-4,11(13)-guaiadien-6α,12-olide 84620-28-0 C19H22O6
1β,10β-Epoxy-3-oxo-8β-isobutyroxy-4,11(13)-guaiadien-6α,12-olide
—— 1α,10α-Epoxy-3-oxo-8β-isobutyroxy-4,11(13)-guaiadien-6α,12-olide 84537-39-3 C19H22O6
1α,10α-Epoxy-3-oxo-8β-isobutyroxy-4,11(13)-guaiadien-6α,12-olide
—— Isobutyric acid (3aR,4R,6aS,9bS)-6a,9-dimethyl-3-methylene-2,6,8-trioxo-2,3,3a,4,5,6,6a,7,8,9b-decahydro-azuleno[4,5-b]furan-4-yl ester 84537-40-6 C19H22O6
Isobutyric acid (3aR,4R,6aS,9bS)-6a,9-dimethyl-3-methylene-2,6,8-trioxo-2,3,3a,4,5,6,6a,7,8,9b-decahydro-azuleno[4,5-b]furan-4-yl ester
—— 3-fluoro-3-oct-1-ynyl-dihydro-furan-2-one 1092696-47-3 C12H17FO2
3-fluoro-3-oct-1-ynyl-dihydro-furan-2-one
—— (6S)-O-(tert-butyldimethylsilyl)-6-hydroxy-7,7-dimethyloxepan-2-one 332950-50-2 C14H28O3Si
(6S)-O-(tert-butyldimethylsilyl)-6-hydroxy-7,7-dimethyloxepan-2-one
—— methyl 3-oxo-2-oxabicyclo<3.3.1>non-7-ene-5-carboxylate 114584-52-0 C10H12O4
methyl 3-oxo-2-oxabicyclo<3.3.1>non-7-ene-5-carboxylate
—— 3,3,5,5-Tetramethyloxane-2,4-dione 86096-13-1 C9H14O3
3,3,5,5-Tetramethyloxane-2,4-dione
—— 1,2-dimethyl-cyclopentane-1,3-dicarboxylic acid-anhydride 26607-00-1 C9H12O3
1,2-dimethyl-cyclopentane-1,3-dicarboxylic acid-anhydride
—— ((3aR,4R,6aS)-2-Oxo-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid 53320-29-9 C9H12O4
((3aR,4R,6aS)-2-Oxo-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid
—— 5-Methyl-5-(1-methyl-cyclopropyl)-dihydro-furan-2-one 68157-84-6 C9H14O2
5-Methyl-5-(1-methyl-cyclopropyl)-dihydro-furan-2-one
—— (3S,4R,5R)-3-Dodecyl-4-hydroxy-5-methyl-dihydro-furan-2-one 385842-94-4 C17H32O3
(3S,4R,5R)-3-Dodecyl-4-hydroxy-5-methyl-dihydro-furan-2-one
—— (4S,5S)-3-Hexadec-(E)-ylidene-4-methoxymethoxy-5-methyl-dihydro-furan-2-one 303008-43-7 C23H42O4
(4S,5S)-3-Hexadec-(E)-ylidene-4-methoxymethoxy-5-methyl-dihydro-furan-2-one
—— (4S,5S)-3-Hexadec-2-yn-(E)-ylidene-4-methoxymethoxy-5-methyl-dihydro-furan-2-one 303008-45-9 C23H38O4
(4S,5S)-3-Hexadec-2-yn-(E)-ylidene-4-methoxymethoxy-5-methyl-dihydro-furan-2-one
—— (3S,4aS,7R,7aS,10R,11aR)-3,7,10-trimethyl-7,7a,8,9,10,11-hexahydro-4aH-[1,2,4]trioxino[6,5-j]isochromen-6-one 120354-72-5 C13H20O5
(3S,4aS,7R,7aS,10R,11aR)-3,7,10-trimethyl-7,7a,8,9,10,11-hexahydro-4aH-[1,2,4]trioxino[6,5-j]isochromen-6-one
—— 4-Bromo-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid 2525-52-2 C8H9BrO4
4-Bromo-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
—— α,β,β,γ-Tetramethyl-γ-valerolacton 39922-59-3 C9H16O2
α,β,β,γ-Tetramethyl-γ-valerolacton
—— 36269-13-3 C14H18O4
—— 2-Ethyliden-3-methyl-γ-butyrolacton 51552-40-0 C7H10O2
2-Ethyliden-3-methyl-γ-butyrolacton
—— (S)-3-Eth-(E)-ylidene-4-methyl-dihydro-furan-2-one 141979-32-0 C7H10O2
(S)-3-Eth-(E)-ylidene-4-methyl-dihydro-furan-2-one
—— oxacycloundec-9-en-2-one 344308-75-4 C10H16O2
oxacycloundec-9-en-2-one
—— (E)-(2-(hydroxymethyl)-4-(8-(methoxymethoxy)octylidene)-5-oxotetrahydrofuran-2-yl)methyl pivalate 1219016-30-4 C21H36O7
(E)-(2-(hydroxymethyl)-4-(8-(methoxymethoxy)octylidene)-5-oxotetrahydrofuran-2-yl)methyl pivalate
—— (4aS,7aR)-5-<(E)-trimethylsilylmethylene>octahydrocyclopenta<b>pyran-2-one 144786-58-3 C12H20O2Si
(4aS,7aR)-5-<(E)-trimethylsilylmethylene>octahydrocyclopenta<b>pyran-2-one
—— (4aS,7aR)-5-<(Z)-trimethylsilylmethylene>octahydrocyclopenta<b>pyran-2-one 144708-93-0 C12H20O2Si
(4aS,7aR)-5-<(Z)-trimethylsilylmethylene>octahydrocyclopenta<b>pyran-2-one
—— Methanesulfonic acid 2,2,5,5-tetramethyl-7-oxo-oxepan-4-yl ester 86838-59-7 C11H20O5S
Methanesulfonic acid 2,2,5,5-tetramethyl-7-oxo-oxepan-4-yl ester
—— Dihydrochrysanthemolacton 22841-82-3 C10H16O2
Dihydrochrysanthemolacton
—— 5,5-diethyldihydro-2-oxofuran-3-carboxaldehyde 1322113-53-0 C9H14O3
5,5-diethyldihydro-2-oxofuran-3-carboxaldehyde
—— (3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 155975-07-8 C14H26O5Si
(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester
—— (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 155882-38-5 C14H26O5Si
(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester
—— 5-methyl-4-n-pentyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-77-0 C21H38O2Si
5-methyl-4-n-pentyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 3-(2-bromoethyl)-3-(2-hydroxyethyl)octanoic acid lactone 203931-68-4 C12H21BrO2
3-(2-bromoethyl)-3-(2-hydroxyethyl)octanoic acid lactone
—— 5-methyl-4-n-pentyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-78-1 C21H38O2Si
5-methyl-4-n-pentyl-7-triisopropylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 5-methyl-4-n-pentyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-70-3 C15H26O2Si
5-methyl-4-n-pentyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— 5-methyl-4-n-pentyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one 1372629-69-0 C15H26O2Si
5-methyl-4-n-pentyl-7-trimethylsislyl-cis-3-oxabicyclo[3.2.0]hept-6-en-2-one
—— (3R,3aR,9aS,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one 90807-58-2 C21H24O2Se
(3R,3aR,9aS,9bR)-3,6-Dimethyl-9-methylene-3-phenylselanyl-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one