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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-methyl-4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone 134163-42-1 C17H34O3Si
2-methyl-4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone
—— 6-[6-(tert-butyldiphenylsilanyloxy)-4-methoxy-2-methylnonyl]-4-hydroxytetrahydropyran-2-one 1229648-39-8 C32H48O5Si
6-[6-(tert-butyldiphenylsilanyloxy)-4-methoxy-2-methylnonyl]-4-hydroxytetrahydropyran-2-one
—— 4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone 134163-41-0 C16H32O3Si
4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone
—— 2,2-dimethyl-4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone 134163-44-3 C18H36O3Si
2,2-dimethyl-4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone
—— (1S,2S,4aR,6S,8S,8aS,4'R,6'R,2''S)-6'<2-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2''-methylbutyryl)oxy>-6-<(Z)-prop-1-enyl>-1-naphthalenyl>ethyl>tetrahydro-4'-hydroxy-2'H-pyran-2'-one 134931-65-0 C26H40O5
(1S,2S,4aR,6S,8S,8aS,4'R,6'R,2''S)-6'<2-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2''-methylbutyryl)oxy>-6-<(Z)-prop-1-enyl>-1-naphthalenyl>ethyl>tetrahydro-4'-hydroxy-2'H-pyran-2'-one
—— (4R,6S,1'S)-6-(1'-Iodopentyl)-4-(triisopropylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one 135677-44-0 C19H37IO3Si
(4R,6S,1'S)-6-(1'-Iodopentyl)-4-(triisopropylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
—— (1S,2S,4aR,6S,8S,8aS,4'R,6'R)-6'<2-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>ethyl>tetrahydro-4'-hydroxy-2'H-pyran-2'-one 134852-63-4 C27H42O5
(1S,2S,4aR,6S,8S,8aS,4'R,6'R)-6'<2-<1,2,4a,5,6,7,8,8a-octahydro-2-methyl-8-<(2'',2''-dimethylbutyryl)oxy>-6-<(E)-prop-1-enyl>-1-naphthalenyl>ethyl>tetrahydro-4'-hydroxy-2'H-pyran-2'-one
—— Methyl 5-methyl-3-oxo-1-phenyl-6-propan-2-ylidene-1,6a-dihydrocyclopenta[c]furan-3a-carboxylate 1192068-07-7 C19H20O4
Methyl 5-methyl-3-oxo-1-phenyl-6-propan-2-ylidene-1,6a-dihydrocyclopenta[c]furan-3a-carboxylate
—— (Z)-3,7-dimethyl-8-hydroxy-6-octenoic acid lactone 81987-48-6 C10H16O2
(Z)-3,7-dimethyl-8-hydroxy-6-octenoic acid lactone
—— 5-[4-(3-ethoxycarbonyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone 1082070-87-8 C14H21NO5
5-[4-(3-ethoxycarbonyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone
—— 5-[4-(3-hexylcarbamoyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone 1082071-04-2 C18H30N2O4
5-[4-(3-hexylcarbamoyl-4,5-dihydro-5-isoxazolyl)butyl]dihydro-2(3H)-furanone
—— Tert-butyl 5-[4-(5-oxooxolan-2-yl)butyl]-4,5-dihydro-1,2-oxazole-3-carboxylate 1082071-09-7 C16H25NO5
Tert-butyl 5-[4-(5-oxooxolan-2-yl)butyl]-4,5-dihydro-1,2-oxazole-3-carboxylate
—— N,N-diethyl-5-[4-(5-oxooxolan-2-yl)butyl]-4,5-dihydro-1,2-oxazole-3-carboxamide 1082071-06-4 C16H26N2O4
N,N-diethyl-5-[4-(5-oxooxolan-2-yl)butyl]-4,5-dihydro-1,2-oxazole-3-carboxamide
—— 2R,4S,5S-6-cyclohexyl-5-amino-2-(2'-methylpropyl)-gamma-hexanolactone hydrochloride 117497-27-5 C16H29NO2*ClH
2R,4S,5S-6-cyclohexyl-5-amino-2-(2'-methylpropyl)-gamma-hexanolactone hydrochloride
—— 5-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid phenethyl ester 223600-86-0 C20H28O4
5-Heptyl-2-oxo-tetrahydro-furan-3-carboxylic acid phenethyl ester
—— eupalmerin acetate 1000396-74-6 C22H32O5
eupalmerin acetate
—— 7-deoxy-2,3:5,6-di-O-isopropylidene-α-D-glycero-D-mannoheptonic acid ε-lactone 329358-72-7 C13H20O6
7-deoxy-2,3:5,6-di-O-isopropylidene-α-D-glycero-D-mannoheptonic acid ε-lactone
—— (S)-7-(hydroxymethyl)oxepan-2-one 1216785-69-1 C7H12O3
(S)-7-(hydroxymethyl)oxepan-2-one
—— 7-deoxy-2,3:4,5-di-O-isopropylidene-L-glycero-D-mannoheptonic acid ε-lactone 329358-70-5 C13H20O6
7-deoxy-2,3:4,5-di-O-isopropylidene-L-glycero-D-mannoheptonic acid ε-lactone
—— 2-(E)-bromomethylene-3(S)-hydroxymethyl-4(S)-pentyl-γ-butyrolactone 163959-28-2 C11H17BrO3
2-(E)-bromomethylene-3(S)-hydroxymethyl-4(S)-pentyl-γ-butyrolactone
—— (4R)-4({[(2S)-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-pyran-2-one 227804-94-6 C12H20N2O3
(4R)-4({[(2S)-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-pyran-2-one
—— (2S,3R,4R)-4-methyl-5-oxo-2-pentyloxolane-3-carboxylic acid 203864-73-7 C11H18O4
(2S,3R,4R)-4-methyl-5-oxo-2-pentyloxolane-3-carboxylic acid
—— (4S,5S)-5-pentyl-4-phenyldihydrofuran-2(3H)-one 142188-53-2 C15H20O2
(4S,5S)-5-pentyl-4-phenyldihydrofuran-2(3H)-one
—— (3S,4R)-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-methyltetrahydro-2H-pyran-2-one 227804-96-8 C13H22N2O3
(3S,4R)-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-methyltetrahydro-2H-pyran-2-one
—— (3S,4R)-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-propyltetrahydro-2H-pyran-2-one 227804-98-0 C15H26N2O3
(3S,4R)-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-propyltetrahydro-2H-pyran-2-one
—— (4R,5S)-4-(1,3-dioxolan-2-yl)-5-pentyloxolan-2-one 244612-57-5 C12H20O4
(4R,5S)-4-(1,3-dioxolan-2-yl)-5-pentyloxolan-2-one
—— (4S,5S)-4-[(E)-(hept-1-enyl)]-5-pentyl-4,5-dihydro-(3H)-furan-2-one 330847-97-7 C16H28O2
(4S,5S)-4-[(E)-(hept-1-enyl)]-5-pentyl-4,5-dihydro-(3H)-furan-2-one
—— (3S,4R)-3-allyl-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-pyran-2-one 227804-95-7 C15H24N2O3
(3S,4R)-3-allyl-4({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-pyran-2-one
—— (3S,4R)-4-({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-(2-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}ethyl)tetrahydro-2H-pyran-2-one 227804-99-1 C20H38N2O4Si
(3S,4R)-4-({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-(2-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}ethyl)tetrahydro-2H-pyran-2-one
—— (3S,4R)-3-benzyl-4-({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-pyran-2-one 227804-97-9 C19H26N2O3
(3S,4R)-3-benzyl-4-({[2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)tetrahydro-2H-pyran-2-one
—— isohomopilopic acid 170207-45-1 C8H12O4
isohomopilopic acid
—— 1-methyl-8-oxaspiro[5.6]dodec-1-ene-3,7-dione 592479-22-6 C12H16O3
1-methyl-8-oxaspiro[5.6]dodec-1-ene-3,7-dione
—— 2-acetyl-2-(3-oxobutyl)-6-hexanolide 592479-14-6 C12H18O4
2-acetyl-2-(3-oxobutyl)-6-hexanolide
—— (S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one 132604-11-6 C6H8O3
(S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one
—— (+)-galiellalactone —— C11H14O3
(+)-galiellalactone
—— Agn-PC-0jtlmu 56817-97-1 C15H24O2
Agn-PC-0jtlmu
—— α-(diethoxyphosphinyl)-ε-caprolactone 122593-66-2 C10H19O5P
α-(diethoxyphosphinyl)-ε-caprolactone
—— 3-<(Z)-(Methoxycarbonyl)methylene>-1-oxacyclopentan-2-one 72001-46-8 C7H8O4
3-<(Z)-(Methoxycarbonyl)methylene>-1-oxacyclopentan-2-one
—— 3-<(Z)-(Methoxycarbonyl)methylene>-5-methyl-1-oxacyclopentan-2-one 72001-51-5 C8H10O4
3-<(Z)-(Methoxycarbonyl)methylene>-5-methyl-1-oxacyclopentan-2-one
—— (Z)-α-(1-chloroheptylidene)-β-ethyl-β-lactone 627526-57-2 C12H19ClO2
(Z)-α-(1-chloroheptylidene)-β-ethyl-β-lactone
—— (+/-)-threo-γ-hydroxy-β-lysine lactone 53990-02-6 C6H12N2O2
(+/-)-threo-γ-hydroxy-β-lysine lactone
—— 3-bromo-4-diethylamino-5-methoxytetrahudrofuran-2-one 88050-92-4 C9H16BrNO3
3-bromo-4-diethylamino-5-methoxytetrahudrofuran-2-one
—— (4R,5R,10R)-4,5-dihydroxy-10-methyloxecane-2,7-dione 1195113-89-3 C10H16O5
(4R,5R,10R)-4,5-dihydroxy-10-methyloxecane-2,7-dione
—— (2R,3S)-5-Eth-(E)-ylidene-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid —— C10H14O4
(2R,3S)-5-Eth-(E)-ylidene-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid
—— (5R)-benzyldihydrofuran-2-one 437606-63-8 C11H12O2
(5R)-benzyldihydrofuran-2-one
—— 3-Methyl-5-propanoyloxan-2-one 89665-32-7 C9H14O3
3-Methyl-5-propanoyloxan-2-one
—— 5-Acetyl-3-methyloxan-2-one 89665-31-6 C8H12O3
5-Acetyl-3-methyloxan-2-one
—— 2-(1-methylthioethylidene)-γ-butyrolactone 96899-36-4 C6H8O2S
2-(1-methylthioethylidene)-γ-butyrolactone
—— 4-Methyl-4-(trichloromethyl)oxetan-2-one 88351-52-4 C5H5Cl3O2
4-Methyl-4-(trichloromethyl)oxetan-2-one
—— Teuscorolide 41515-46-2 C19H18O5
Teuscorolide