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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-[(tert-butyldimethylsilyloxy)methyl]-5,5-dimethyl-4,7-dioxatetracyclo[7.3.1.0(2,6).0(6,13)]tridecan-3-one 1315247-23-4 C20H34O4Si
2-[(tert-butyldimethylsilyloxy)methyl]-5,5-dimethyl-4,7-dioxatetracyclo[7.3.1.0(2,6).0(6,13)]tridecan-3-one
—— (4R,6R)-3-Acetyl-4-ethyl-6-methyl-5,6-dihydro-4λ<sup>4</sup>-[1,4]oxathiin-2-one 71254-58-5 C9H14O3S
(4R,6R)-3-Acetyl-4-ethyl-6-methyl-5,6-dihydro-4λ<sup>4</sup>-[1,4]oxathiin-2-one
—— 4-(3-methylphenyl)-tetrahydropyran-2-one 1126906-70-4 C12H14O2
4-(3-methylphenyl)-tetrahydropyran-2-one
—— (±)-4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-one 1404301-92-3 C13H24O3Si
(±)-4-(t-butyldimethylsilanyloxymethyl)-4-vinyl-dihydro-furan-2-one
—— 3-dimethylaminomethylene-5-methyltetronic acid 79099-15-3 C8H11NO3
3-dimethylaminomethylene-5-methyltetronic acid
—— 3-[2-Ethyl-hex-(Z)-ylidene]-dihydro-furan-2-one 6285-30-9 C12H20O2
3-[2-Ethyl-hex-(Z)-ylidene]-dihydro-furan-2-one
—— tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate 1416253-53-6 C19H35NO5Si
tert-butyl ((2R,3R,E)-3-((tert-butyldimethylsilyl)oxy)-1-(2-oxodihydrofuran-3(2H)-ylidene)butan-2-yl)carbamate
—— (E)-3-(4-oxo-4-cyclopropylbutylidene)ihydrofuran-2(3H)-one 643754-18-1 C11H14O3
(E)-3-(4-oxo-4-cyclopropylbutylidene)ihydrofuran-2(3H)-one
—— Vermeerin 16983-23-6 C15H20O4
Vermeerin
—— (3S,4R)-3-Allyl-4-hydroxymethyl-dihydro-furan-2-one 75584-29-1 C8H12O3
(3S,4R)-3-Allyl-4-hydroxymethyl-dihydro-furan-2-one
—— 6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone 200728-42-3 C6H9N3O3
6-azido-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone
—— 6-azido-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone 261722-05-8 C12H23N3O3Si
6-azido-5-tert-butyldimethylsilyloxy-2,3,6-trideoxy-D-erythro-hexono-1,4-lactone
—— (3R,4R)-3-methyldecan-4-olide 147254-32-8 C11H20O2
(3R,4R)-3-methyldecan-4-olide
—— (+/-)-3-Chloro-4,4-dimethyl-3-methyloxetan-2-one 193746-39-3 C6H9ClO2
(+/-)-3-Chloro-4,4-dimethyl-3-methyloxetan-2-one
—— 4-methylnonanolide 127997-57-3 C10H18O2
4-methylnonanolide
—— 8-deoxylactucin 65725-10-2 C15H16O4
8-deoxylactucin
—— 3-Hydroxyoxepan-2-one 80816-54-2 C6H10O3
3-Hydroxyoxepan-2-one
—— 3-methyloctanolide 127974-00-9 C9H16O2
3-methyloctanolide
—— 5-(1-bromo-2-methyl-1-propenyl)-tetrahydro-2-furanone 81036-70-6 C8H11BrO2
5-(1-bromo-2-methyl-1-propenyl)-tetrahydro-2-furanone
—— (R)-4-Isopropyl-5-methyl-6-oxo-tetrahydro-pyran-2-carbonitrile 897041-72-4 C10H15NO2
(R)-4-Isopropyl-5-methyl-6-oxo-tetrahydro-pyran-2-carbonitrile
—— (4S,4aS,7R,7aR)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[2-[(2R,3S,4S)-4-hydroxy-2-(methoxymethoxy)-3-(2-methoxypropan-2-yl)oxan-4-yl]-1,3-dithian-2-yl]-4,4a,7,7a-tetrahydro-3H-cyclopenta[b]pyran-2-one 897043-92-4 C30H52O8S2Si
(4S,4aS,7R,7aR)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[2-[(2R,3S,4S)-4-hydroxy-2-(methoxymethoxy)-3-(2-methoxypropan-2-yl)oxan-4-yl]-1,3-dithian-2-yl]-4,4a,7,7a-tetrahydro-3H-cyclopenta[b]pyran-2-one
—— (4S,5S)-3-butyl-4-hydroxy-5-methyltetrahydro-2-furanone 486990-21-0 C9H16O3
(4S,5S)-3-butyl-4-hydroxy-5-methyltetrahydro-2-furanone
—— (3S,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-5-(hydroxymethyl)-3-[(2R)-1,1,1-trifluorobutan-2-yl]dihydrofuran-2(3H)-one 1532540-68-3 C15H27F3O4Si
(3S,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-5-(hydroxymethyl)-3-[(2R)-1,1,1-trifluorobutan-2-yl]dihydrofuran-2(3H)-one
—— [(1'R,2'S,3'R,6'R,7'S)-2'-methyl-5'-oxospiro[1,3-dioxolane-2,10'-4-oxatricyclo[5.3.0.02,6]decane]-3'-yl]methyl 2,2-dimethylpropanoate 162238-46-2 C18H26O6
[(1'R,2'S,3'R,6'R,7'S)-2'-methyl-5'-oxospiro[1,3-dioxolane-2,10'-4-oxatricyclo[5.3.0.02,6]decane]-3'-yl]methyl 2,2-dimethylpropanoate
—— [(1'R,2'S,3'R,6'R,7'S)-2'-methyl-5'-oxospiro[1,3-dioxolane-2,8'-4-oxatricyclo[5.3.0.02,6]decane]-3'-yl]methyl 2,2-dimethylpropanoate 162238-45-1 C18H26O6
[(1'R,2'S,3'R,6'R,7'S)-2'-methyl-5'-oxospiro[1,3-dioxolane-2,8'-4-oxatricyclo[5.3.0.02,6]decane]-3'-yl]methyl 2,2-dimethylpropanoate
—— 4α-carboxy-13α,17-dihydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone 1168152-29-1 C20H30O5
4α-carboxy-13α,17-dihydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone
—— 3-methyl-3-(3-oxo-butyl)-furan-2,4-dione 1236161-64-0 C9H12O4
3-methyl-3-(3-oxo-butyl)-furan-2,4-dione
—— 4-(2-methyl-2-propenyl)-γ-butyrolactone 134359-17-4 C8H12O2
4-(2-methyl-2-propenyl)-γ-butyrolactone
—— 1-(3-Bromophenyl)-3-oxabicyclo[3.2.0]heptane-2,4-dione 1125407-00-2 C12H9BrO3
1-(3-Bromophenyl)-3-oxabicyclo[3.2.0]heptane-2,4-dione
—— (5R)-5-butyl-5-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[tert-butyl(diphenyl)silyl]oxyethyl]oxolan-2-one 250379-00-1 C32H50O4Si2
(5R)-5-butyl-5-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[tert-butyl(diphenyl)silyl]oxyethyl]oxolan-2-one
—— (R)-5-[(R)-bromo(phenyl)methyl]oxolan-2-one 1379786-11-4 C11H11BrO2
(R)-5-[(R)-bromo(phenyl)methyl]oxolan-2-one
—— 5-ethoxycarbonyl-5-(n-undecyl)-δ-valerolactone 553668-27-2 C19H34O4
5-ethoxycarbonyl-5-(n-undecyl)-δ-valerolactone
—— 9-decen-5-olide 74585-00-5 C10H16O2
9-decen-5-olide
—— (3S,4R)-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone 202846-65-9 C9H14O4
(3S,4R)-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone
—— (3S,4S)-3-Hydroxy-4-methyl-4-vinyl-dihydro-furan-2-one 202846-68-2 C7H10O3
(3S,4S)-3-Hydroxy-4-methyl-4-vinyl-dihydro-furan-2-one
—— (3S,4S)-4-(2-hydroxyethyl)-3-methoxymethyloxy-4-methyl-γ-butyrolactone 202846-64-8 C9H16O5
(3S,4S)-4-(2-hydroxyethyl)-3-methoxymethyloxy-4-methyl-γ-butyrolactone
—— 6-(tert-butyldimethylsilyloxy)-2,3-dideoxy-5-mesyloxy-L-threo-hexono-1,4-lactone 244275-88-5 C13H26O6SSi
6-(tert-butyldimethylsilyloxy)-2,3-dideoxy-5-mesyloxy-L-threo-hexono-1,4-lactone
—— 5-azido-6-(tert-butyldimethylsilyloxy)-2,3-dideoxy-D-erythro-hexono-1,4-lactone 244275-89-6 C12H23N3O3Si
5-azido-6-(tert-butyldimethylsilyloxy)-2,3-dideoxy-D-erythro-hexono-1,4-lactone
—— 6-(tert-butyldimethylsilyloxy)-2,3-dideoxy-L-threo-hexono-1,4-lactone 244275-87-4 C12H24O4Si
6-(tert-butyldimethylsilyloxy)-2,3-dideoxy-L-threo-hexono-1,4-lactone
—— (+/-)-3,6,6-trimethyl-(4a<i>r</i>,8a<i>c</i>)-hexahydro-3<i>t</i>,5<i>t</i>-ethano-pyrano[3,4-<i>c</i>]pyran-1,8-dione 5988-79-4 C13H18O4
(+/-)-3,6,6-trimethyl-(4a<i>r</i>,8a<i>c</i>)-hexahydro-3<i>t</i>,5<i>t</i>-ethano-pyrano[3,4-<i>c</i>]pyran-1,8-dione
—— Citryliden-malonsaeure 5988-79-4 C13H18O4
Citryliden-malonsaeure
—— 2(3H)-Furanone, dihydro-5-tridecyl- 110071-72-2 C17H32O2
2(3H)-Furanone, dihydro-5-tridecyl-
—— (1S,4S,5S)-spiro[bicyclo[2.2.1]hept-2-ene-5,3'-oxolane]-2'-one 1063984-38-2 C10H12O2
(1S,4S,5S)-spiro[bicyclo[2.2.1]hept-2-ene-5,3'-oxolane]-2'-one
—— 5-ethyl-4-methyl-dihydro-furan-2,3-dione 16431-44-0 C7H10O3
5-ethyl-4-methyl-dihydro-furan-2,3-dione
—— (4-acetyl-5-oxotetrahydrofuran-3-yl)methyl dimethyl phosphate 1309477-55-1 C9H15O7P
(4-acetyl-5-oxotetrahydrofuran-3-yl)methyl dimethyl phosphate
—— 4-fluoromethyl-dihydro-furan-2-one 813452-00-5 C5H7FO2
4-fluoromethyl-dihydro-furan-2-one
—— 7-methyl-2-oxa-7-azaspiro[4.4]nonan-1-one 389578-65-8 C8H13NO2
7-methyl-2-oxa-7-azaspiro[4.4]nonan-1-one
—— (rac)-3-[(cyclopentylamino)methyl]dihydro-2(3H)-furanone 1062243-60-0 C10H17NO2
(rac)-3-[(cyclopentylamino)methyl]dihydro-2(3H)-furanone
—— 3-((Z)-3-Ethoxy-allyl)-dihydro-furan-2-one 323181-60-8 C9H14O3
3-((Z)-3-Ethoxy-allyl)-dihydro-furan-2-one
—— 4-[2-cyclohexylethyl]-4-hydroxy-4,5-dihydrofuran-2(3H)-one 249766-76-5 C12H20O3
4-[2-cyclohexylethyl]-4-hydroxy-4,5-dihydrofuran-2(3H)-one