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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
—— 4-Methoxy-cyclohexan-diessigsaeure-(1,1)-anhydrid 91352-86-2 C11H16O4
—— trans-5-allyl-4-ethyl-4,5-dihydro-2(3H)-furanone 121756-24-9 C9H14O2
—— (2S,4R,5R)-4-hydroxy-2-(methoxymethyl)-2-methyl-5-phenyloxolan-3-one 126045-22-5 C13H16O4
—— 5-Oxa-dispiro[2.0.4.5]tridecan-6-one 72331-85-2 C12H18O2
—— (-)-(S)-4-pentyl-4,5-dihydrofuran-2(3H)-one 123975-91-7 C9H16O2
—— 8-methyl-3,5,11-trioxo-oleandolide 111734-79-3 C20H30O6
—— (4R<sup>*</sup>,5S<sup>*</sup>)-4-tert-butyl-4-hydroxy-5-methyl-1-oxacyclohexan-2-one 136085-25-1 C10H18O3
—— (1R,5S)-6-((E)-benzylidene)-3-oxabicyclo[3.1.0]hexan-2-one 1613445-93-4 C12H10O2
—— (-)-(R)-γ-(2-furyl)-γ-butyrolactone 1429482-66-5 C8H8O3
—— 3α-(hydroxymethyl)-1α-methyl-1β-(methoxycarbonyl)cyclohex-4-ene-2α-carboxylic acid γ-lactone 77044-50-9 C11H14O4
—— 3-Methyl-3-phenyl-5-hydroxy-tetrahydrofuranon-(2) 31005-33-1 C11H12O3
—— 3(R<sup>*</sup>)-hydroxy-4(S<sup>*</sup>)-methyl-5(R<sup>*</sup>)-isopropyltetrahydrofuran-2-one 106470-99-9 C8H14O3
—— trichloro-6,6,6 hexanolide-4 98325-68-9 C6H7Cl3O2
—— tetrahydro-3,3-bis(3-iodopropyl)-2(2H)-pyranone 163012-23-5 C11H18I2O2
—— 2(3H)-Furanone, dihydro-5-(iodomethyl)-4-methyl-, (4R,5S)-rel- 65371-40-6 C6H9IO2
—— 3-ethyl-5-(hydroxymethyl)-3-prop-2-enyloxolan-2-one 80758-90-3 C10H16O3
—— 4-allyl-2-oxabicyclo<3.3.0>-6-octen-3-one 143790-18-5 C10H12O2
—— 5,9-Dimethyl-hexahydro-1,7-dioxa-cyclopenta[e]azulene-2,4,8-trione 106478-52-8 C13H16O5
—— (<i>S</i>)-2-((3a<i>R</i>,7a<i>S</i>)-1ξ,7<i>t</i>-dihydroxy-3a,3b-dimethyl-3-oxo-(3a<i>r</i>)-hexahydro-benzo[1,3]cyclopropa[1,2-<i>c</i>]furan-6<i>c</i>-yl)-propionic acid 110030-84-7 C14H20O6
—— 5-Heptyl-3-hydroxy-3-methyl-dihydro-furan-2-one 318472-49-0 C12H22O3
—— Isobutyric acid (3S,3aR,4R,6R,6aR,9bS)-6-hydroxy-3,6,9-trimethyl-2,8-dioxo-2,3,3a,4,5,6,6a,7,8,9b-decahydro-azuleno[4,5-b]furan-4-yl ester 110188-57-3 C19H26O6
—— 5-iodomethyl-3-tetradecanylidenedihydro-2(3H)-furanone 84938-62-5 C19H33IO2
—— 6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.03.9]nonane 21321-57-3 C10H14O2
—— (4aR,6R,8S,8aR)-6,8-bis[[tert-butyl(dimethyl)silyl]oxy]-1,4,4a,5,6,7,8,8a-octahydroisochromen-3-one 546125-82-0 C21H42O4Si2
—— (S)-5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one 1217263-86-9 C11H11ClO2
—— (1R,4S,5R,8S)-8-bromo-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one 65825-61-8 C7H7BrO3
—— 3-Ethoxycarbonyl-2-hexyl-2-methyl-tetrahydrofuran-5-on 93807-60-4 C14H24O4
—— ethyl 2-cyano-4-methylene-5-oxotetrahydrofuran-2-carboxylate 1529773-09-8 C9H9NO4
—— 3-(Methyl-diphenyl-silanyl)-tetrahydro-pyran-2-one 77772-26-0 C18H20O2Si
—— 5-(1,1-Difluoro-2-hydroxy-ethyl)-dihydro-furan-2-one 205311-95-1 C6H8F2O3
—— tannunolide A 110209-99-9 C15H18O2
—— C6-Epi-desoxo-dihydro-allo-isotenulin 111531-08-9 C17H26O4
—— trans-5-ethoxymethyl-3-phenylselenotetrahydrofuran-2-one 112233-26-8 C13H16O3Se
—— 4,4-dimethyl-5-phenyldihydrofuran-2(3H)-one 105640-04-8 C12H14O2
—— Acetic acid (3aR,4S,5S,6S,6aR)-6-bromo-4-methoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 56460-53-8 C11H15BrO5
—— 2(3H)-Furanone, dihydro-3-(1-propenyl)-, (Z)- 90292-23-2 C7H10O2
—— 1228699-46-4 C17H22O6
—— methyl 5-(iodomethyl)-2-oxooxolane-3-carboxylate 141869-02-5 C7H9IO4
—— 3-Ethyl-5-(1-iodo-2-trimethylsilanyl-ethyl)-4-methyl-dihydro-furan-2-one 87441-58-5 C12H23IO2Si
—— (1S*,3aR*,8aS*)-hexahydro-8a-hydroxy-3H-1,3a-ethano-1H-cyclohepta<c>furan-3-one 124439-14-1 C11H16O3
—— 2,3,3aα,4,5,6,7,7aα-octahydro-4β-hydroxy-6α-methoxycarbonyl-6β-methyl-3α-(4-methyl-3-pentenyl)-1-benzofuran-2-one 81470-30-6 C17H26O5
—— 5,8-Dihydroxy-1,4,4a,5,6,7,8,8a-octahydro-<1>naphthoesaeure-1->8-lacton 91970-89-7 C11H14O3
—— 3-(2-methyl-2-(triethylsilylperoxy)heptyl)dihydrofuran-2(3H)-one 1321200-07-0 C18H36O4Si
—— (3S)-3-ethyl-3-(3-hydroxypropyl)-5-methoxyoxolan-2-one 111154-16-6 C10H18O4
—— 1438388-50-1 C12H21O6S*Na
—— (2R)-2,3-dideoxy-2-ethyl-2-(2-propenyl)-D-glyceropentanoic acid γ-lactone 81075-90-3 C10H16O3
—— 1-benzyl-4,4-dimethyl-3,7-dioxabicyclo<3.3.0>octane-2,8-dione 133472-35-2 C15H16O4
—— methyl 2-[(3aS,4S,6S,6aS)-2-oxo-6-phenylselanyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]acetate 117109-89-4 C16H18O4Se
—— Ethyl 5-hydroxy-1-oxo-7-phenyl-1,3,4,7-tetrahydrobenzo[c]furan-6-carboxylate 103122-13-0 C17H16O5
—— 2,2-Dimethyl-propionic acid (S)-5-oxo-tetrahydro-furan-3-ylmethyl ester 134665-19-3 C10H16O4