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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
—— 3-(3-cyclohexyl-2-methyl-2-(triethylsilylperoxy)propyl)-3-methyldihydrofuran-2(3H)-one 1321200-03-6 C21H40O4Si
3-(3-cyclohexyl-2-methyl-2-(triethylsilylperoxy)propyl)-3-methyldihydrofuran-2(3H)-one
—— 6-butyl-4-methyltetrahydro-2H-pyran-2-one 57058-21-6 C10H18O2
6-butyl-4-methyltetrahydro-2H-pyran-2-one
—— 3-methyl-3-(2-methyl-2-(triethylsilylperoxy)propyl)dihydrofuran-2(3H)-one 1321199-98-7 C15H30O4Si
3-methyl-3-(2-methyl-2-(triethylsilylperoxy)propyl)dihydrofuran-2(3H)-one
—— S-(+)-α-benzyl-α-methyl-γ-butyrolactone 719282-77-6 C12H14O2
S-(+)-α-benzyl-α-methyl-γ-butyrolactone
—— 3-methyl-3-(2-methylallyl)dihydrofuran-2(3H)-one 208394-29-0 C9H14O2
3-methyl-3-(2-methylallyl)dihydrofuran-2(3H)-one
—— γ-methyl decalactone —— C11H20O2
γ-methyl decalactone
—— 4-Methyl-6-propyloxan-2-one 1298089-12-9 C9H16O2
4-Methyl-6-propyloxan-2-one
—— α-benzyl-α-methyl-γ-butyrolactone 22421-36-9 C12H14O2
α-benzyl-α-methyl-γ-butyrolactone
—— 3-(2-(2-ethylphenyl)-1-hydroxyethyl)-3-methyldihydrofuran-2(3H)-one 1321200-13-8 C15H20O3
3-(2-(2-ethylphenyl)-1-hydroxyethyl)-3-methyldihydrofuran-2(3H)-one
—— 3-methyl-3-phenethyldihydrofuran-2(3H)-one 1321199-87-4 C13H16O2
3-methyl-3-phenethyldihydrofuran-2(3H)-one
—— 3-(3-cyclohexyl-2-methylallyl)-3-methyldihydrofuran-2(3H)-one 1321199-92-1 C15H24O2
3-(3-cyclohexyl-2-methylallyl)-3-methyldihydrofuran-2(3H)-one
—— α-Hydroxycarbonyl-α-methyl-γ-butyrolacton 7473-09-8 C6H8O4
α-Hydroxycarbonyl-α-methyl-γ-butyrolacton
—— 2-(3-butenyl)-4-butanolide 142636-40-6 C8H12O2
2-(3-butenyl)-4-butanolide
—— 5-hydroxy-3-phenyl-hexanoic acid-lactone 18397-38-1 C12H14O2
5-hydroxy-3-phenyl-hexanoic acid-lactone
—— (E)-2-<(trimethylsilyl)methylene>-4-butanolide 150615-32-0 C8H14O2Si
(E)-2-<(trimethylsilyl)methylene>-4-butanolide
—— 2-oxo-N-pentyltetrahydrofuran-3-sulfonamide 1345963-97-4 C9H17NO4S
2-oxo-N-pentyltetrahydrofuran-3-sulfonamide
—— 2-oxo-tetrahydro-furan-3-sulfonyl chloride 40336-84-3 C4H5ClO4S
2-oxo-tetrahydro-furan-3-sulfonyl chloride
—— N-pentyl-2-oxotetrahydrofuran-3-carboxamide 1345963-98-5 C10H17NO3
N-pentyl-2-oxotetrahydrofuran-3-carboxamide
—— 6-acetyltetrahydro-2H-pyran-2-one 486405-21-4 C7H10O3
6-acetyltetrahydro-2H-pyran-2-one
—— (5R)-3-[(E)-but-2-enoyl]-5-(triphenylsilylmethyl)oxolan-2-one 936005-49-1 C27H26O3Si
(5R)-3-[(E)-but-2-enoyl]-5-(triphenylsilylmethyl)oxolan-2-one
—— 2-ethylidenehept-5-en-4-olide 61097-39-0 C9H12O2
2-ethylidenehept-5-en-4-olide
—— α-(4-hydroxybutyl)-γ-butyrolactone 203259-86-3 C8H14O3
α-(4-hydroxybutyl)-γ-butyrolactone
—— 4-propylthio-4,5-dihydrofuran-2(3H)-one 25516-01-2 C7H12O2S
4-propylthio-4,5-dihydrofuran-2(3H)-one
—— [(1S,3R,7S,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] 2,2-dimethylbutanoate;2-aminoethanesulfonic acid —— C27H45NO8S
[(1S,3R,7S,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] 2,2-dimethylbutanoate;2-aminoethanesulfonic acid
—— 3-(4,5-Dioxo-3-phenyloxolan-2-yl)propanoic acid —— C13H12O5
3-(4,5-Dioxo-3-phenyloxolan-2-yl)propanoic acid
—— 3-(4-Hydroxy-5-oxo-3-phenyloxolan-2-yl)propanoic acid —— C13H14O5
3-(4-Hydroxy-5-oxo-3-phenyloxolan-2-yl)propanoic acid
—— (7Z)-7-butylideneoxepan-2-one —— C10H16O2
(7Z)-7-butylideneoxepan-2-one
—— (2R,8R,10S,17R,18R)-17-(furan-3-yl)-2,7,7,18-tetramethyl-6,9,16-trioxapentacyclo[11.7.0.02,8.08,10.014,18]icosa-3,12-diene-5,11,15-trione —— C25H26O7
(2R,8R,10S,17R,18R)-17-(furan-3-yl)-2,7,7,18-tetramethyl-6,9,16-trioxapentacyclo[11.7.0.02,8.08,10.014,18]icosa-3,12-diene-5,11,15-trione
—— (1S,10S,13R,17R)-8-chloro-5-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-12-hydroxy-10,13-dimethyl-4,11,15-trioxatetracyclo[8.7.0.02,7.012,17]heptadeca-2,5,7-triene-9,16-dione —— C25H29ClO6
(1S,10S,13R,17R)-8-chloro-5-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-12-hydroxy-10,13-dimethyl-4,11,15-trioxatetracyclo[8.7.0.02,7.012,17]heptadeca-2,5,7-triene-9,16-dione
—— [(E)-1-[(3S,5S)-3,8,8-trimethyl-1,6-dioxo-2,7-dioxaspiro[4.4]nonan-3-yl]ethylideneamino]thiourea —— C13H19N3O4S
[(E)-1-[(3S,5S)-3,8,8-trimethyl-1,6-dioxo-2,7-dioxaspiro[4.4]nonan-3-yl]ethylideneamino]thiourea
—— (2E)-2-[1-(5-methyl-2-oxo-3-propanoyltetrahydrofuran-3-yl)propan-2-ylidene]hydrazinecarbothioamide —— C12H19N3O3S
(2E)-2-[1-(5-methyl-2-oxo-3-propanoyltetrahydrofuran-3-yl)propan-2-ylidene]hydrazinecarbothioamide
—— N'-[(1E)-1-(4-bromophenyl)ethylidene]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide —— C18H21BrN2O3
N'-[(1E)-1-(4-bromophenyl)ethylidene]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide
—— N'-[(E)-(2-chlorophenyl)methylidene]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide —— C17H19ClN2O3
N'-[(E)-(2-chlorophenyl)methylidene]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbohydrazide
—— N-[(E)-benzylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide —— C17H20N2O3
N-[(E)-benzylideneamino]-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxamide
—— (2E)-2-[1-(4-hexyl-2-methyl-5-oxotetrahydrofuran-2-yl)ethylidene]hydrazinecarboxamide —— C14H25N3O3
(2E)-2-[1-(4-hexyl-2-methyl-5-oxotetrahydrofuran-2-yl)ethylidene]hydrazinecarboxamide
—— (2E)-2-[1-(4-butyl-5-oxotetrahydrofuran-2-yl)ethylidene]hydrazinecarboxamide —— C11H19N3O3
(2E)-2-[1-(4-butyl-5-oxotetrahydrofuran-2-yl)ethylidene]hydrazinecarboxamide
—— (2E)-2-[4-(2-oxo-5-pentyltetrahydrofuran-3-yl)butan-2-ylidene]hydrazinecarboxamide —— C14H25N3O3
(2E)-2-[4-(2-oxo-5-pentyltetrahydrofuran-3-yl)butan-2-ylidene]hydrazinecarboxamide
—— (2E)-2-[4-(2-oxo-5-pentyltetrahydrofuran-3-yl)butan-2-ylidene]hydrazinecarbothioamide —— C14H25N3O2S
(2E)-2-[4-(2-oxo-5-pentyltetrahydrofuran-3-yl)butan-2-ylidene]hydrazinecarbothioamide
—— 4-[(1R,5S)-5-methyl-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]butanenitrile —— C12H15NO2
4-[(1R,5S)-5-methyl-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]butanenitrile
—— 4-[(1S,5R)-5-methyl-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]butanenitrile —— C12H15NO2
4-[(1S,5R)-5-methyl-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]butanenitrile
—— 3-[(1S,5R)-5-methyl-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]propanenitrile —— C11H13NO2
3-[(1S,5R)-5-methyl-7-oxo-6-oxabicyclo[3.2.1]oct-2-en-1-yl]propanenitrile
—— (1S,4S)-7,7-dimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid —— C9H12O4
(1S,4S)-7,7-dimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
—— (1R,4R)-7,7-dimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid —— C9H12O4
(1R,4R)-7,7-dimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
—— 2-(4-Heptyl-5-oxo-tetrahydro-furan-2-ylmethyl)-isothiourea —— C13H25BrN2O2S
2-(4-Heptyl-5-oxo-tetrahydro-furan-2-ylmethyl)-isothiourea
—— (1R,5S)-5,8,8-trimethyl-2,4-dioxo-N-(2,2,2-trifluoroethyl)-3-oxabicyclo[3.2.1]octane-1-carboxamide —— C13H16F3NO4
(1R,5S)-5,8,8-trimethyl-2,4-dioxo-N-(2,2,2-trifluoroethyl)-3-oxabicyclo[3.2.1]octane-1-carboxamide
—— (2R,3S)-2-heptyl-5-oxooxolane-3-carboxylate —— C12H19O4-
(2R,3S)-2-heptyl-5-oxooxolane-3-carboxylate
—— (5R)-3-hydroxy-5-[(1S)-1-hydroxy-2-[(2R)-2-hydroxy-2-[(2R)-4-hydroxy-3,5-dioxooxolan-2-yl]ethyl]sulfanylethyl]oxolane-2,4-dione —— C12H14O10S
(5R)-3-hydroxy-5-[(1S)-1-hydroxy-2-[(2R)-2-hydroxy-2-[(2R)-4-hydroxy-3,5-dioxooxolan-2-yl]ethyl]sulfanylethyl]oxolane-2,4-dione
—— 2-[(2S,4S)-2-[(1S,3R,5S)-3,5-dimethyl-2-oxocyclohexyl]-6-oxooxan-4-yl]acetamide —— C15H23NO4
2-[(2S,4S)-2-[(1S,3R,5S)-3,5-dimethyl-2-oxocyclohexyl]-6-oxooxan-4-yl]acetamide
—— 2-[(2S,4S)-2-[(1S,3R,5R)-3,5-dimethyl-2-oxocyclohexyl]-6-oxooxan-4-yl]acetamide —— C15H23NO4
2-[(2S,4S)-2-[(1S,3R,5R)-3,5-dimethyl-2-oxocyclohexyl]-6-oxooxan-4-yl]acetamide
—— (1R,5R,5'S,8R,9R,10R)-5'-(furan-3-yl)-5-hydroxy-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4(12)-ene-9,3'-oxolane]-2',3-dione —— C19H20O6
(1R,5R,5'S,8R,9R,10R)-5'-(furan-3-yl)-5-hydroxy-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4(12)-ene-9,3'-oxolane]-2',3-dione