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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
—— 2-[(4Z)-4-(1-bromoethylidene)-5-oxooxolan-3-yl]acetaldehyde 193620-89-2 C8H9BrO3
2-[(4Z)-4-(1-bromoethylidene)-5-oxooxolan-3-yl]acetaldehyde
—— (+/-)-syn,anti-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone 1003-88-9 C6H10O3
(+/-)-syn,anti-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone
—— tert-butyl (R)-((R)-3-acetyl-2-oxotetrahydrofuran-3-yl)(thiophen-2-yl)methylcarbamate 1232237-95-4 C16H21NO5S
tert-butyl (R)-((R)-3-acetyl-2-oxotetrahydrofuran-3-yl)(thiophen-2-yl)methylcarbamate
—— 4-ethyl-5-oxo-tetrahydro-furan-3-carboxylic acid 4436-05-9 C7H10O4
4-ethyl-5-oxo-tetrahydro-furan-3-carboxylic acid
—— 3-acetyl-3-(3-(dimethylamino)propyl)dihydrofuran-2(3H)-one 1622868-70-5 C11H19NO3
3-acetyl-3-(3-(dimethylamino)propyl)dihydrofuran-2(3H)-one
—— 3-acetyl-3-(2-(pyrrolidin-1-yl)ethyl)dihydrofuran-2(3H)-one 1622868-67-0 C12H19NO3
3-acetyl-3-(2-(pyrrolidin-1-yl)ethyl)dihydrofuran-2(3H)-one
—— α-acetyl-α-(β-methylallyl)-γ-butyrolactone 128815-26-9 C10H14O3
α-acetyl-α-(β-methylallyl)-γ-butyrolactone
—— 3-acetyl-3-(2-(diethylamino)ethyl)dihydrofuran-2(3H)-one 1622868-68-1 C12H21NO3
3-acetyl-3-(2-(diethylamino)ethyl)dihydrofuran-2(3H)-one
—— (3R)-3-[(1S)-1-hydroxyethyl]oxolan-2-one —— C6H10O3
(3R)-3-[(1S)-1-hydroxyethyl]oxolan-2-one
—— α-acetyl-α-allyl-γ-butyrolactone 114709-93-2 C9H12O3
α-acetyl-α-allyl-γ-butyrolactone
—— (4S)-(E)-dehydrohomopilopic aldehyde 144128-28-9 C8H10O3
(4S)-(E)-dehydrohomopilopic aldehyde
—— 3-<1-(trimethylsiloxy)ethylidene>dihydro-2(3H)-furanone 221317-22-2 C9H16O3Si
3-<1-(trimethylsiloxy)ethylidene>dihydro-2(3H)-furanone
—— α-(2-Tetrahydrofuranylidene)-γ-butyrolactone 65652-24-6 C8H10O3
α-(2-Tetrahydrofuranylidene)-γ-butyrolactone
—— (+)-isopilocarpidine 13640-27-2 C10H14N2O2
(+)-isopilocarpidine
—— (-)-(3S,1'R)-α-1'-hydroxyethyl-γ-butyrolactone 1003-88-9 C6H10O3
(-)-(3S,1'R)-α-1'-hydroxyethyl-γ-butyrolactone
—— α-bromo-α-acetyl-butyrolactone 98198-52-8 C6H7BrO3
α-bromo-α-acetyl-butyrolactone
—— isohomopilopic aldehyde 144128-27-8 C8H12O3
isohomopilopic aldehyde
—— 2-hydroxy-6-hexanolide 78002-77-4 C6H10O3
2-hydroxy-6-hexanolide
—— (2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one 130514-52-2 C21H27NO5
(2'R,2''S,3''S,4R,5S,5''R)-(+)-<2'-(3'',5''-dimethyl-6''-oxotetrahydropyran-2''-yl)-1'-oxobutyl>-4-methyl-5-phenyloxazolidin-2-one
—— β-benzyl-γ-butyrolactone 126434-64-8 C11H12O2
β-benzyl-γ-butyrolactone
—— 6-((3Z,6Z,9Z)-1-iodopentadeca-3,6,9-trien-1-yl)tetrahydro-2Hpyran-2-one 742103-77-1 C20H31IO2
6-((3Z,6Z,9Z)-1-iodopentadeca-3,6,9-trien-1-yl)tetrahydro-2Hpyran-2-one
—— 4-hydroxy-4-methyl-3-pentyl-tetrahydrofuran-2-one 142227-92-7 C10H18O3
4-hydroxy-4-methyl-3-pentyl-tetrahydrofuran-2-one
—— dimethyldiketene 26638-94-8 C6H8O2
dimethyldiketene
—— 6-oxo-tetrahydro-pyran-3-carboxylic acid 5807-38-5 C6H8O4
6-oxo-tetrahydro-pyran-3-carboxylic acid
—— 8,8-dimethyl-1-oxa-spiro[4.5]decan-2-one 96517-19-0 C11H18O2
8,8-dimethyl-1-oxa-spiro[4.5]decan-2-one
—— (5S,1'S)-5-<1'-<N-(tert-Butoxycarbonyl)amino>-3'-methylbutyl>dihydrofuran-2(3H)-one 105018-81-3 C14H25NO4
(5S,1'S)-5-<1'-<N-(tert-Butoxycarbonyl)amino>-3'-methylbutyl>dihydrofuran-2(3H)-one
—— (3R,5S)-5-[(1'S)-1-(N-Boc-amino)-3-methylbutyl]-3-methyl-dihydrofuran-2(3H)-one 169057-47-0 C15H27NO4
(3R,5S)-5-[(1'S)-1-(N-Boc-amino)-3-methylbutyl]-3-methyl-dihydrofuran-2(3H)-one
—— (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one 137567-91-0 C8H10O2
(+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one
—— 4-phenyl-2-methylenebutyrolactone 26613-71-8 C11H10O2
4-phenyl-2-methylenebutyrolactone
—— 4-chloromethyl-β-lactone 6737-16-2 C4H5ClO2
4-chloromethyl-β-lactone
—— 3-(2-hydroxy-ethylsulfanyl)-dihydro-furan-2-one 1156934-21-2 C6H10O3S
3-(2-hydroxy-ethylsulfanyl)-dihydro-furan-2-one
—— 3-acetyl-5-ethyldihydro-2(3H)-furanone 3620-19-7 C8H12O3
3-acetyl-5-ethyldihydro-2(3H)-furanone
—— (1R,6S)-7-Oxa-bicyclo[4.2.0]oct-2-en-8-one 65656-92-0 C7H8O2
(1R,6S)-7-Oxa-bicyclo[4.2.0]oct-2-en-8-one
—— α-ethylidene-γ-butyrolactone 21053-56-5 C6H8O2
α-ethylidene-γ-butyrolactone
—— oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester 42564-36-3 C8H10O5
oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester
—— 3-Methylene-4-(1-methylethyl)-1-oxetan-2-one 117203-18-6 C7H10O2
3-Methylene-4-(1-methylethyl)-1-oxetan-2-one
—— methyl 5-methylene-2-oxo-3-phenyltetrahydro-2H-pyran-3-carboxylate 958000-84-5 C14H14O4
methyl 5-methylene-2-oxo-3-phenyltetrahydro-2H-pyran-3-carboxylate
—— α-(n-Butylcarbamoyl)-γ-butyrolacton 52217-14-8 C9H15NO3
α-(n-Butylcarbamoyl)-γ-butyrolacton
—— α-benzyl-γ-methylidene-δ-valerolactone 98754-13-3 C13H14O2
α-benzyl-γ-methylidene-δ-valerolactone
—— α,α-(1,5-dithiapentylene)-γ-methylidene-δ-valerolactone 1306830-29-4 C9H12O2S2
α,α-(1,5-dithiapentylene)-γ-methylidene-δ-valerolactone
—— α-methyl-α-phenyl-γ-methylidene-δ-valerolactone 1306830-30-7 C13H14O2
α-methyl-α-phenyl-γ-methylidene-δ-valerolactone
—— α-methoxycarbonyl-α-benzyl-γ-methylidene-δ-valerolactone 1095991-76-6 C15H16O4
α-methoxycarbonyl-α-benzyl-γ-methylidene-δ-valerolactone
—— α,α-dimethyl-γ-methylidene-δ-valerolactone 1306830-28-3 C8H12O2
α,α-dimethyl-γ-methylidene-δ-valerolactone
—— [(1S,3R,7R,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxybutanoate —— C23H34O6
[(1S,3R,7R,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (3R)-3-hydroxybutanoate
—— (3aS,4R,9aR,9bS)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione —— C15H16O5
(3aS,4R,9aR,9bS)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
—— (5S)-3-Fluoro-tetrahydro-5-[(hydroxy)methyl]-2(3H)-furanone 134455-76-8 C5H7FO3
(5S)-3-Fluoro-tetrahydro-5-[(hydroxy)methyl]-2(3H)-furanone
—— 2-(5-oxo-4-oxa-5-homoadamantane-1-yl)oxymethoxy-2-oxoethylchloride 1338917-19-3 C13H17ClO5
2-(5-oxo-4-oxa-5-homoadamantane-1-yl)oxymethoxy-2-oxoethylchloride
—— 3-allyl-tetrahydropyran-2-one 50994-84-8 C8H12O2
3-allyl-tetrahydropyran-2-one
—— cis-cis-Puleganolid 391669-84-4 C10H16O2
cis-cis-Puleganolid
—— (3aS,6R,6aR)-hexahydro-3,3,6-trimethyl-6a-(2'-propenyl)-1H-cyclopenta[c]furan-1-one 402561-77-7 C13H20O2
(3aS,6R,6aR)-hexahydro-3,3,6-trimethyl-6a-(2'-propenyl)-1H-cyclopenta[c]furan-1-one