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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
—— cis-4-Phenyl-5-isopropyldihydro-2(3H)-furanone —— C13H16O2
cis-4-Phenyl-5-isopropyldihydro-2(3H)-furanone
—— (4R,5S)-5-Butyl-4-phenyl-dihydro-furan-2-one —— C14H18O2
(4R,5S)-5-Butyl-4-phenyl-dihydro-furan-2-one
—— 3-methyloctahydro-2H-cyclohepta[b]furan-2-one 33366-33-5 C10H16O2
3-methyloctahydro-2H-cyclohepta[b]furan-2-one
—— Carbonic acid allyl ester (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester 848893-30-1 C31H44O7Si2
Carbonic acid allyl ester (2R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester
—— 3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone 848893-31-2 C30H44O5Si2
3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone
—— 4,5-dihydro-3-trimethylsilylmethylene-2(3H)-furanone 121767-12-2 C8H14O2Si
4,5-dihydro-3-trimethylsilylmethylene-2(3H)-furanone
—— (E)-3-propylidenetetrahydro-2H-pyran-2-one 98011-26-8 C8H12O2
(E)-3-propylidenetetrahydro-2H-pyran-2-one
—— ethyl 2-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)acetate 16838-73-6 C10H16O4
ethyl 2-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)acetate
—— 1-Oxacycloundecane-2,8-dione 16121-19-0 C10H16O3
1-Oxacycloundecane-2,8-dione
—— 3-[1-Hydroxyamino-eth-(Z)-ylidene]-5-methyl-furan-2,4-dione 78752-10-0 C7H9NO4
3-[1-Hydroxyamino-eth-(Z)-ylidene]-5-methyl-furan-2,4-dione
—— (-)-2-chloro-2,3-dideoxy-D-arabino-hexono-1,4-lactone 128503-31-1 C6H9ClO4
(-)-2-chloro-2,3-dideoxy-D-arabino-hexono-1,4-lactone
—— (S,S,S,S)-2,5-dihydroxy-3-(N-tert-butoxycarbonylamino)-7-(triisopropylsilyloxy)-4-heptylolactone 1422373-49-6 C21H41NO7Si
(S,S,S,S)-2,5-dihydroxy-3-(N-tert-butoxycarbonylamino)-7-(triisopropylsilyloxy)-4-heptylolactone
—— 3-[(2S,3S,4S,5R)-4-tert-butyldimethylsilyloxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-(E)-propenal 515868-90-3 C16H28O4Si
3-[(2S,3S,4S,5R)-4-tert-butyldimethylsilyloxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-(E)-propenal
—— 4-tert-butyldimethylsilyloxy-3,5-dimethyl-6-oxotetrahydropyran-2-carbaldehyde 515869-00-8 C14H26O4Si
4-tert-butyldimethylsilyloxy-3,5-dimethyl-6-oxotetrahydropyran-2-carbaldehyde
—— 2-[(3R,5R)-5-[(1S)-1-hydroxypropyl]-2-oxooxolan-3-yl]acetaldehyde 877762-73-7 C9H14O4
2-[(3R,5R)-5-[(1S)-1-hydroxypropyl]-2-oxooxolan-3-yl]acetaldehyde
—— (3R,4R)-(+)-cis-dimethyl-(γ)-butyrolactone 90026-55-4 C6H10O2
(3R,4R)-(+)-cis-dimethyl-(γ)-butyrolactone
—— (4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one 139403-50-2 C14H18O2Se
(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one
—— 4-methyl-octahydro-cyclohepta[<i>b</i>]pyran-2-one 774-31-2 C11H18O2
4-methyl-octahydro-cyclohepta[<i>b</i>]pyran-2-one
—— γ,γ,δ-trimethyl-δ-valerolactone 78238-80-9 C8H14O2
γ,γ,δ-trimethyl-δ-valerolactone
—— Spiro<1,3,5-cycloheptatrien-7,3'-tetrahydrofuran>-2'-on 63227-71-4 C10H10O2
Spiro<1,3,5-cycloheptatrien-7,3'-tetrahydrofuran>-2'-on
—— 4-acetyl-2-methyl-5-oxo-tetrahydro-furan-2-carbonitrile 52135-54-3 C8H9NO3
4-acetyl-2-methyl-5-oxo-tetrahydro-furan-2-carbonitrile
—— 4-cyano-trans-5,8-diphenyl-2-oxabicyclo<2.2.2>octan-3-one 111904-77-9 C20H17NO2
4-cyano-trans-5,8-diphenyl-2-oxabicyclo<2.2.2>octan-3-one
—— 2-C-methyl-D-lyxono-1,4-lactone 53008-96-1 C6H10O5
2-C-methyl-D-lyxono-1,4-lactone
—— 2-C-methyl-D-xylono-1,4-lactone 53008-97-2 C6H10O5
2-C-methyl-D-xylono-1,4-lactone
—— 2-Benzyl-glutarsaeure-anhydrid 112635-23-1 C12H12O3
2-Benzyl-glutarsaeure-anhydrid
—— 5-Butyl-5-ethyl-3-methylene-dihydro-furan-2-one 82415-94-9 C11H18O2
5-Butyl-5-ethyl-3-methylene-dihydro-furan-2-one
—— 4-(4-methylphenyl)dihydropyran-2,6-dione 91963-20-1 C12H12O3
4-(4-methylphenyl)dihydropyran-2,6-dione
—— 4-(5-oxo-tetrahydro-[2]furyl)-butyronitrile 98593-35-2 C8H11NO2
4-(5-oxo-tetrahydro-[2]furyl)-butyronitrile
—— 2-Oxo-3-propyloxolane-3-carbonyl chloride 82672-11-5 C8H11ClO3
2-Oxo-3-propyloxolane-3-carbonyl chloride
—— 4,4-Diethyl-3-methylene-1-oxetan-2-one 136066-41-6 C8H12O2
4,4-Diethyl-3-methylene-1-oxetan-2-one
—— α,α-Diethyl-glutarsaeureanhydrid 143096-21-3 C9H14O3
α,α-Diethyl-glutarsaeureanhydrid
—— (R)-4-ethyltetrahydropyran-2-one 71301-88-7 C7H12O2
(R)-4-ethyltetrahydropyran-2-one
—— 3-epi-compactin 84173-30-8 C23H34O5
3-epi-compactin
—— (S)-dihydro-5-(3-methylbut-2-enyl)furan-2(3H)-one 85428-32-6 C9H14O2
(S)-dihydro-5-(3-methylbut-2-enyl)furan-2(3H)-one
—— 6,8-Dimethyl-1-oxaspiro<4.5>decan-2-one 135974-86-6 C11H18O2
6,8-Dimethyl-1-oxaspiro<4.5>decan-2-one
—— 1-Oxaspiro<4.5>dec-7-en-2-one 135974-78-6 C9H12O2
1-Oxaspiro<4.5>dec-7-en-2-one
—— (+/-)-anti-2,4-dimethylglutaric anhydride 4295-92-5 C7H10O3
(+/-)-anti-2,4-dimethylglutaric anhydride
—— sundiversifolide 935875-77-7 C13H20O3
sundiversifolide
—— (3R,3aR,7S,8aR,Z)-6-(2-hydroxyethyl)-3,7-dimethyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 225518-67-2 C13H20O3
(3R,3aR,7S,8aR,Z)-6-(2-hydroxyethyl)-3,7-dimethyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
—— (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 935733-55-4 C28H36O3Si
(3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
—— (3S,5S)-3,5-dimethyltetrahydropyran-2-one 849464-79-5 C7H12O2
(3S,5S)-3,5-dimethyltetrahydropyran-2-one
—— (2S,4S)-2,4-dimethylglutaric anhydride 118139-25-6 C7H10O3
(2S,4S)-2,4-dimethylglutaric anhydride
—— (2S,4S)-5-(2,4-dimethylheptyl)-3,4,5,6-tetrahydro-4-hydroxy-3-methyl-2H-pyran-2-one 332035-29-7 C15H28O3
(2S,4S)-5-(2,4-dimethylheptyl)-3,4,5,6-tetrahydro-4-hydroxy-3-methyl-2H-pyran-2-one
—— (2R,4R)-5-(2,4-dimethylheptyl)-3,4,5,6-tetrahydro-4-hydroxy-3-methyl-2H-pyran-2-one 332035-28-6 C15H28O3
(2R,4R)-5-(2,4-dimethylheptyl)-3,4,5,6-tetrahydro-4-hydroxy-3-methyl-2H-pyran-2-one
—— (+)-(2S,4R)-cis-2,4-dimethyl-δ-valerolactone 75658-88-7 C7H12O2
(+)-(2S,4R)-cis-2,4-dimethyl-δ-valerolactone
—— 5,5-Dicyclopropyl-2-oxo-3-methoxycarbonyltetrahydrofuran 82968-81-8 C12H16O4
5,5-Dicyclopropyl-2-oxo-3-methoxycarbonyltetrahydrofuran
—— 3S,5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-4,5-dihydro-2(3H)-furanone 147200-09-7 C22H28O3Si
3S,5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-4,5-dihydro-2(3H)-furanone
—— methyl (1S,4aS,8R,8aS)-8-hydroxy-1-methyl-3-oxo-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylate 74848-77-4 C11H14O6
methyl (1S,4aS,8R,8aS)-8-hydroxy-1-methyl-3-oxo-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylate
—— (1R,5S)-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one 1040833-47-3 C10H14O2
(1R,5S)-7,7-dimethyl-1-vinyl-2-oxabicyclo[3.2.0]heptan-3-one
—— (-)-xylomollin 61229-34-3 C12H18O7
(-)-xylomollin