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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-oxo-3-methylene-4-(1-cis-propenyl)tetrahydrofuran 86747-77-5 C8H10O2
2-oxo-3-methylene-4-(1-cis-propenyl)tetrahydrofuran
—— methyl trans-2-methyl-5-oxotetrahydro-3-furancarboxylate —— C7H10O4
methyl trans-2-methyl-5-oxotetrahydro-3-furancarboxylate
—— 3,3-Dichloro-5-(2,2-dichloroethenyl)-4,4-dimethyloxolan-2-one 202519-12-8 C8H8Cl4O2
3,3-Dichloro-5-(2,2-dichloroethenyl)-4,4-dimethyloxolan-2-one
—— 5-(2,2-dichlorovinyl)-4,4-dimethyl-2-oxotetrahydrofuran 61820-12-0 C8H10Cl2O2
5-(2,2-dichlorovinyl)-4,4-dimethyl-2-oxotetrahydrofuran
—— (2S)-2-[(2R,4R)-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-6-oxooxan-2-yl]propanal 353521-08-1 C16H30O4Si
(2S)-2-[(2R,4R)-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-6-oxooxan-2-yl]propanal
—— (2S,4S)-4-azido-2-isopropyl-4-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]butanal 173154-02-4 C14H23N3O3
(2S,4S)-4-azido-2-isopropyl-4-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]butanal
—— (3S,3aR,6aR)-3a,4-dihydro-3-hydroxy-3H-cyclopenta[b]furan-2(6aH)-one 151765-22-9 C7H8O3
(3S,3aR,6aR)-3a,4-dihydro-3-hydroxy-3H-cyclopenta[b]furan-2(6aH)-one
—— Corey-aldehyde 122517-79-7 C11H18O4Si
Corey-aldehyde
—— 1082301-61-8 C7H12O2S
—— Acetic acid (2aR,6R,8S,8aR,8bS)-8b-hydroxy-1,1,2a,6-tetramethyl-5-oxo-decahydro-4-oxa-acenaphthylen-8-yl ester 52988-64-4 C17H26O5
Acetic acid (2aR,6R,8S,8aR,8bS)-8b-hydroxy-1,1,2a,6-tetramethyl-5-oxo-decahydro-4-oxa-acenaphthylen-8-yl ester
—— O-ethyl S-(2-oxotetrahydrofuran-3-yl) carbonodithioate 66909-39-5 C7H10O3S2
O-ethyl S-(2-oxotetrahydrofuran-3-yl) carbonodithioate
—— 3α-hydroxycurcumalactone 1552288-08-0 C15H24O3
3α-hydroxycurcumalactone
—— 6-((1E,3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl)tetrahydro-2H-pyran-2-one 375387-75-0 C20H28O2
6-((1E,3Z,6Z,9Z,12Z)-pentadeca-1,3,6,9,12-pentaen-1-yl)tetrahydro-2H-pyran-2-one
—— (+/-)-Cantharsaeure —— C10H12O4
(+/-)-Cantharsaeure
—— 2β-hydroxycurcumalactone 1552288-10-4 C15H24O3
2β-hydroxycurcumalactone
—— (1R,4R,5S)-4,5-dimethyl-3-oxa-bicyclo-<3.2.0>-heptan-2-one 165544-76-3 C8H12O2
(1R,4R,5S)-4,5-dimethyl-3-oxa-bicyclo-<3.2.0>-heptan-2-one
—— 3,3:17,17-bis[1,2-ethenediylbis(oxy)]-11β-hydroxyestr-5-en-18-oic acid γ-lactone 59860-72-9 C22H28O6
3,3:17,17-bis[1,2-ethenediylbis(oxy)]-11β-hydroxyestr-5-en-18-oic acid γ-lactone
—— 6-methyltetrahydropyran-2,4-dione 85825-79-2 C6H8O3
6-methyltetrahydropyran-2,4-dione
—— dimeres Butylketen 5659-17-6 C12H20O2
dimeres Butylketen
—— ethyl 2-oxo-1-oxaspiro<4,5>decane-4-carboxylate 61858-03-5 C12H18O4
ethyl 2-oxo-1-oxaspiro<4,5>decane-4-carboxylate
—— ethyl 2-oxo-1-oxaspiro[4.6]undecane-4-carboxylate 33021-07-7 C13H20O4
ethyl 2-oxo-1-oxaspiro[4.6]undecane-4-carboxylate
—— ethyl 2-oxo-1-oxaspiro[4.4]nonane-4-carboxylate 61858-02-4 C11H16O4
ethyl 2-oxo-1-oxaspiro[4.4]nonane-4-carboxylate
—— 5-iodomethyl-dihydro-furan-2-one 1729-32-4 C5H7IO2
5-iodomethyl-dihydro-furan-2-one
—— (S)-2-((2S,3R,4R)-3,4-Dihydroxy-5-oxotetrahydrofuran-2-yl)-2-hydroxyacetic acid hydrate —— C6H10O8
(S)-2-((2S,3R,4R)-3,4-Dihydroxy-5-oxotetrahydrofuran-2-yl)-2-hydroxyacetic acid hydrate
—— L-ascorbic acid 1128-23-0 C6H10O6
L-ascorbic acid
—— Dehydro-L-ascorbic acid 490-83-5 C6H6O6
Dehydro-L-ascorbic acid
—— (1S,2R,6S,7R)-2-acetyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 82111-81-7 C11H12O3
(1S,2R,6S,7R)-2-acetyl-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
—— 4<i>c</i>-(3-amino-2-oxo-propyl)-3<i>r</i>-ethyl-dihydro-furan-2-one 46186-40-7 C9H15NO3
4<i>c</i>-(3-amino-2-oxo-propyl)-3<i>r</i>-ethyl-dihydro-furan-2-one
—— (4R)-(Z)-dehydrohomopilopic aldehyde 144128-26-7 C8H10O3
(4R)-(Z)-dehydrohomopilopic aldehyde
—— 2-[(3R,4S)-4-ethyl-5-oxo-tetrahydro-3-furanyl]acetaldehyde 144128-27-8 C8H12O3
2-[(3R,4S)-4-ethyl-5-oxo-tetrahydro-3-furanyl]acetaldehyde
—— 3-acetyl-3-phenylselenyl-3H-dihydrofuran-2-one 85217-83-0 C12H12O3Se
3-acetyl-3-phenylselenyl-3H-dihydrofuran-2-one
—— 5-oxo-4-oxa-5-homoadamantane-1-ol 96314-52-2 C10H14O3
5-oxo-4-oxa-5-homoadamantane-1-ol
—— 2-anti-hydroxy-4-oxa-5-homoadamantan-5-one 79499-77-7 C10H14O3
2-anti-hydroxy-4-oxa-5-homoadamantan-5-one
—— D-<i>glycero</i>-D-<i>allo</i>-heptonic acid-4-lactone —— C7H12O7
D-<i>glycero</i>-D-<i>allo</i>-heptonic acid-4-lactone
—— D-allono-1,4-lactone 29474-78-0 C6H10O6
D-allono-1,4-lactone
—— 4-Hydroxymethyl-5-phenyl-dihydro-furan-2-one 132949-20-3 C11H12O3
4-Hydroxymethyl-5-phenyl-dihydro-furan-2-one
—— L-erythrono-1,4-lactone 17675-99-9 C4H6O4
L-erythrono-1,4-lactone
—— 3-[Hydroxy(phenyl)methyl]oxan-2-one 113426-29-2 C12H14O3
3-[Hydroxy(phenyl)methyl]oxan-2-one
—— 4-ethyl-4-methyl-tetrahydro-pyran-2-one 15025-17-9 C8H14O2
4-ethyl-4-methyl-tetrahydro-pyran-2-one
—— camphanoylchlorid 49620-91-9 C10H13ClO3
camphanoylchlorid
—— (3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 187851-98-5 C28H32O3SeSi
(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one
—— andrographolide 1360179-87-8 C20H30O5
andrographolide
—— 7-(β-cyanoethyl)oxepan-2-one 32805-32-6 C9H13NO2
7-(β-cyanoethyl)oxepan-2-one
—— artemisinin G 98379-74-9 C15H22O5
artemisinin G
—— 4-ethyl-2-methyl-4-butyrolactone 2610-98-2 C7H12O2
4-ethyl-2-methyl-4-butyrolactone
—— 2-methyl-4-propyl-4-butyrolactone 2610-97-1 C8H14O2
2-methyl-4-propyl-4-butyrolactone
—— galiellalactone 133613-71-5 C11H14O3
galiellalactone
—— (4R,6S)-6-(chloromethyl)-4-hydroxytetrahydropyran-2-one 391218-14-7 C6H9ClO3
(4R,6S)-6-(chloromethyl)-4-hydroxytetrahydropyran-2-one
—— 2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone 69617-72-7 C6H8Br2O4
2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone
—— 5-(3-chloropropanyloxy)-2-hexyl-hexadecanoic 1,3-lactone 338964-15-1 C25H47ClO3
5-(3-chloropropanyloxy)-2-hexyl-hexadecanoic 1,3-lactone