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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
—— methyl (2Z)-2-(4-methyl-2-oxo-1-oxaspiro[4.5]decan-3-ylidene)acetate 72163-22-5 C13H18O4
methyl (2Z)-2-(4-methyl-2-oxo-1-oxaspiro[4.5]decan-3-ylidene)acetate
—— 3-ethyl-5-methyl-2,4(3H,5H)-furandione 10385-34-9 C7H10O3
3-ethyl-5-methyl-2,4(3H,5H)-furandione
—— 4-tert-Butyldimethylsilyl-5'-chloro-4a'-hydroxy-6'-(hydroxyimino)methyl Simvastatin —— C31H52ClNO7Si
4-tert-Butyldimethylsilyl-5'-chloro-4a'-hydroxy-6'-(hydroxyimino)methyl Simvastatin
—— (-)-(2S,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid 681179-41-9 C6H8O4
(-)-(2S,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid
—— Bznzmrjnzlbsjb-gqanposxsa- 108893-57-8 C15H20O3
Bznzmrjnzlbsjb-gqanposxsa-
—— 4-Methyl-3-pent-4-enyloxetan-2-one 247216-22-4 C9H14O2
4-Methyl-3-pent-4-enyloxetan-2-one
—— (3aS,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-4,5-bis(methoxymetthoxy)-5-methyl-2H-cyclopenta[b]furan-2-one 832078-82-7 C12H20O6
(3aS,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-4,5-bis(methoxymetthoxy)-5-methyl-2H-cyclopenta[b]furan-2-one
—— Methanesulfonic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester 251958-12-0 C7H12O5S
Methanesulfonic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester
—— ethyl (2R,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylate 681179-50-0 C8H12O4
ethyl (2R,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylate
—— ethyl (-)-(2S,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylate 681179-39-5 C8H12O4
ethyl (-)-(2S,3S)-2-methyl-5-oxotetrahydro-3-furancarboxylate
—— (3aS,4R,6R,6aR)-4-(tert-butyldimethylsilyloxy)-6-hydroxy-6-methyl-hexahydrocyclopenta[b]furan-2-one 832078-85-0 C14H26O4Si
(3aS,4R,6R,6aR)-4-(tert-butyldimethylsilyloxy)-6-hydroxy-6-methyl-hexahydrocyclopenta[b]furan-2-one
—— (3aS,4R,6R,6aR)-4-(tert-butyldimethylsilyloxy)-6-(methoxymethyl)-6-methyl-hexahydrocyclopenta[b]furan-2-one 832078-86-1 C16H30O5Si
(3aS,4R,6R,6aR)-4-(tert-butyldimethylsilyloxy)-6-(methoxymethyl)-6-methyl-hexahydrocyclopenta[b]furan-2-one
—— (3R,3aS,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-hydroxy-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one 832078-89-4 C12H20O7
(3R,3aS,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-hydroxy-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one
—— (-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid 681179-42-0 C6H8O4
(-)-(2S,3R)-2-methyl-5-oxotetrahydro-3-furancarboxylic acid
—— (3R,4S,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one 62232-31-9 C6H10O4
(3R,4S,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one
—— (3S,4R,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one 13964-32-4 C6H10O4
(3S,4R,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one
—— 4-(1-tert-Butyl-2,2-dimethyl-propylidene)-3,3,5,5-tetramethyl-dihydro-furan-2-one 124992-74-1 C17H30O2
4-(1-tert-Butyl-2,2-dimethyl-propylidene)-3,3,5,5-tetramethyl-dihydro-furan-2-one
—— (3R,4R)-3,4-Dimethylpentan-5-olide 78148-72-8 C7H12O2
(3R,4R)-3,4-Dimethylpentan-5-olide
—— (1S,5R)-α-methylene-2-oxabicyclo[3.3.0]oct-6-en-3-one 1294506-20-9 C8H8O2
(1S,5R)-α-methylene-2-oxabicyclo[3.3.0]oct-6-en-3-one
—— (E)-4-isopropyl-7-oxooct-5-en-4-olide 129742-48-9 C11H16O3
(E)-4-isopropyl-7-oxooct-5-en-4-olide
—— (1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde 51260-12-9 C8H8O3
(1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde
—— 3-(1-hydroxycyclooctyl)-1-oxaspiro<4.7>dodecan-2-one 137170-81-1 C19H32O3
3-(1-hydroxycyclooctyl)-1-oxaspiro<4.7>dodecan-2-one
—— (+)-(1S,5R)-3-oxabicyclo[3.3.0]oct-6-en-2-one 103618-27-5 C7H8O2
(+)-(1S,5R)-3-oxabicyclo[3.3.0]oct-6-en-2-one
—— (1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one 26054-65-9 C10H14O5
(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one
—— 3-oxabicyclo[3.3.0]oct-6-en-2-one —— C7H8O2
3-oxabicyclo[3.3.0]oct-6-en-2-one
—— (4S,5S)-4-[(1S)-1,2-dihydroxyethyl]-3-methylidene-5-pentyloxolan-2-one 218908-83-9 C12H20O4
(4S,5S)-4-[(1S)-1,2-dihydroxyethyl]-3-methylidene-5-pentyloxolan-2-one
—— 3-(1-hydroxycycloheptyl)-1-oxaspiro<4.6>undecan-2-one 137170-80-0 C17H28O3
3-(1-hydroxycycloheptyl)-1-oxaspiro<4.6>undecan-2-one
—— (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether 64072-30-6 C21H38O4Si
(3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3-tert-butyldimethylsilyl ether
—— 1-oxaspiro[4.11]hexadecan-2-one 18214-80-7 C15H26O2
1-oxaspiro[4.11]hexadecan-2-one
—— 3-(1-hydroxycyclopentyl)-1-oxaspiro<4.4>nonan-2-one 137170-78-6 C13H20O3
3-(1-hydroxycyclopentyl)-1-oxaspiro<4.4>nonan-2-one
—— (3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 87727-92-2 C21H36O3Si
(3aR,4R,6aS)-4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
—— 1-Benzoxepin-2,7(3H,8H)-dione, 4,5,9,9a-tetrahydro-9a-methyl- 281224-82-6 C11H14O3
1-Benzoxepin-2,7(3H,8H)-dione, 4,5,9,9a-tetrahydro-9a-methyl-
—— (4aS,7aR)-1,3,4,4a-hexahydro-cyclopenta[c]pyran-3-one 371783-62-9 C8H10O2
(4aS,7aR)-1,3,4,4a-hexahydro-cyclopenta[c]pyran-3-one
—— (1R,5S)-4,4-dichloro-2-oxabicyclo<3.3.0>oct-6-en-3-one 162425-53-8 C7H6Cl2O2
(1R,5S)-4,4-dichloro-2-oxabicyclo<3.3.0>oct-6-en-3-one
—— 4-hydroxy-5,5-dimethyl-tetrahydro-pyran-2-one 149909-56-8 C7H12O3
4-hydroxy-5,5-dimethyl-tetrahydro-pyran-2-one
—— (1S*,5R*)-3-oxabicyclo<3.3.0>octan-2-one 5733-03-9 C7H10O2
(1S*,5R*)-3-oxabicyclo<3.3.0>octan-2-one
—— (3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 187851-99-6 C12H14O3Se
(3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one
—— D-digitoxonic acid lactone 132741-54-9 C6H10O4
D-digitoxonic acid lactone
—— 5-(3-hydroxypropyl)dihydrofuran-2(3H)-one 69186-21-6 C7H12O3
5-(3-hydroxypropyl)dihydrofuran-2(3H)-one
—— 5-(2,2-difluoroethyl)dihydrofuran-2(3H)-one 1337445-75-6 C6H8F2O2
5-(2,2-difluoroethyl)dihydrofuran-2(3H)-one
—— 5-(2-fluoroethyl)dihydrofuran-2(3H)-one 1337445-73-4 C6H9FO2
5-(2-fluoroethyl)dihydrofuran-2(3H)-one
—— 6-(fluoromethyl)tetrahydro-2H-pyran-2-one 1337445-77-8 C6H9FO2
6-(fluoromethyl)tetrahydro-2H-pyran-2-one
—— 3,5-Diethyl-3,5-dimethyl-dihydro-furan-2-one 85688-23-9 C10H18O2
3,5-Diethyl-3,5-dimethyl-dihydro-furan-2-one
—— 6-(chloromethyl)tetrahydropyran-2-one 77944-06-0 C6H9ClO2
6-(chloromethyl)tetrahydropyran-2-one
—— 5,5-dimethyl-3-methylene-4-phenyldihydrofuran-2(3H)-one 63506-92-3 C13H14O2
5,5-dimethyl-3-methylene-4-phenyldihydrofuran-2(3H)-one
—— 3-(5-oxotetrahydro-2-furanyl)propanoic acid 6283-72-3 C7H10O4
3-(5-oxotetrahydro-2-furanyl)propanoic acid
—— 3-methylene-4-phenyldihydrofuran-2(3H)-one 35630-42-3 C11H10O2
3-methylene-4-phenyldihydrofuran-2(3H)-one
—— cis-3-methylene-4-phenyl-5-methyltetrahydrofuran-2-one —— C12H12O2
cis-3-methylene-4-phenyl-5-methyltetrahydrofuran-2-one
—— 1,3,3,4',4'-Pentamethyl-5,5'-dioxobicyclo<4.2.1>nonane-7-spiro-2'-(tetrahydrofuran)-6-carboxylic acid 128064-26-6 C18H26O5
1,3,3,4',4'-Pentamethyl-5,5'-dioxobicyclo<4.2.1>nonane-7-spiro-2'-(tetrahydrofuran)-6-carboxylic acid
—— (4S)-4-(1-chloro-1-methylethyl)tetrahydrofuran-2-one 93782-31-1 C7H11ClO2
(4S)-4-(1-chloro-1-methylethyl)tetrahydrofuran-2-one