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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
—— 2-Oxaspiro[5.5]undecan-1-one 83558-39-8 C10H16O2
—— 1,4,4-Trimethyl-2-oxo-3-oxabicyclo<3.1.0>hexan-6-carbaldehyd 111061-99-5 C9H12O3
—— 2,2-Dimethyl-propionic acid (3aR,4aR,6R,8aR,9aR)-8a-methyl-5-methylene-2-oxo-dodecahydro-naphtho[2,3-b]furan-6-yl ester 54370-69-3 C19H28O4
—— (R)-3-Benzyl-5-hexyl-3-phenylselanyl-dihydro-furan-2-one 55229-22-6 C23H28O2Se
—— (2S,4S)-2-ethyl-4-(hydroxymethyl)-2-methyl-4-butanolide 80348-83-0 C8H14O3
—— 3,6-dideoxy-L-arabino-hexono-1,5-lactone 69992-17-2 C6H10O4
—— (4aR,8aR)-Tetrahydro-pyrano[4,3-c]pyran-3,7-dione 145433-61-0 C8H10O4
—— 3-methyl-2-oxo-5-(2,2,2-trichloroethyl)tetrahydrofuran 136311-58-5 C7H9Cl3O2
—— (4R,5S)-5-butyl-4-(dimethyl(phenyl)silyl)dihydrofuran-2(3H)-one 1436857-02-1 C16H24O2Si
—— <3α(R*),3aα,7aα>-(+/-)-3a,6,7,7a-tetrahydro-3-(1-methyl-2-propenyl)-2(3H)-benzofuranone 108712-47-6 C12H16O2
—— (4R,6R)-6-[(3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yloxy]-4-isobutyl-1,3-oxazinan-2-one 1360566-16-0 C14H23NO5
—— 3-(1-ethoxyethoxy)-5-methyl-3-propyloxolan-2-one 86749-55-5 C12H22O4
—— (6E,10E)-(3aR,4R,8S)-4,8-Dihydroxy-3-methoxymethyl-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one 38456-38-1 C16H24O5
—— 8-Hydroxy-14,15-thapsanolide 102358-31-6 C15H24O3
—— (5-oxotetrahydrofuran-2-yl)methyl formate 57859-04-8 C6H8O4
—— 88567-36-6 C15H17BrO4
—— 2,2,4a-Trimethyl-1,3-dioxolo<4,5-f>perhydroisobenzofuran-5-on 124804-09-7 C12H18O4
—— 2-acetoxymethyl-2,5-anhydro-3-deoxy-D-threo-pentono-1,4-lactone 111507-17-6 C8H10O5
—— (1α,2β,5α,7β)-2-methyl-3-oxobicyclo<3.3.0>octane-2,7-carbolactone 99902-57-5 C10H12O3
—— (3aR,5aR,7R,9aR,9bR)-7-(1-Hydroxy-1-methyl-ethyl)-3a,9a-dimethyl-decahydro-furo[3,2-f]chromen-2-one 60371-97-3 C16H26O4
—— (3aR,4R,5R,6aS)-4-Formyl-2-oxo-hexahydro-cyclopenta[b]furan-5-carboxylic acid methyl ester 65914-66-1 C10H12O5
—— (9S,11aR)-8-Hydroxy-3,11a-dimethyl-9-methylamino-3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-tetradecahydro-3H-2-oxa-pentaleno[1,6a-a]phenanthren-1-one 23494-90-8 C22H33NO3
—— (1S,5R)-8-Ethyl-9-methyl-3-methylene-6-oxa-bicyclo[3.2.2]non-8-en-7-one 118496-27-8 C12H16O2
—— 58698-17-2 C18H25BrO4
—— 2α-bromo-3β-methyl-4β-phenyl-γ-butyrolactone 99344-38-4 C11H11BrO2
—— (2S,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-carbaldehyde 81661-43-0 C12H22O4Si
—— Methyltetrahydromonoepoxyovatodiolat 62862-55-9 C21H30O5
—— (3aS,7aR)-6,6-Dimethyl-3,3-diphenyl-hexahydro-benzofuran-2,4-dione 54166-41-5 C22H22O3
—— Tetrahydro-6a-methyl-1H-cyclopenta<c>furan-1,6(3H)-dione 134906-26-6 C8H10O3
—— 4,4,5-trimethyl-5-phenyldihydrofuran-2(3H)-one 29200-53-1 C13H16O2
—— N,N′-((2aS,2a1R,4S,4aS,6S,7S,7aS)-6,7-dihydroxy-4-methoxy-6-methyl-2-oxooctahydro-2H-1,3-dioxacyclopenta[cd]inden-2a1-yl)bis-carbamic acid C,C′-bis(1,1-dimethylethyl) ester 1421851-13-9 C22H35N3O10
—— 6,7-bis(chloromethyl)-4-(pivaloyloxymethyl)-3-oxabicyclo[3.2.0]heptan-2-one 1323991-04-3 C14H20Cl2O4
—— 3-[(R)-2-(triisopropylsiloxy)butyl]-5,5-dimethyl-2,4(3H,5H)-furandione 1402731-56-9 C19H34O5Si
—— 4<i>t</i>,5<i>t</i>-dimethyl-3<i>r</i>-prop-2-ynyl-dihydro-furan-2-one 62850-90-2 C9H12O2
—— (4R,5R)-4-Phenyl-5-((E)-propenyl)-dihydro-furan-2-one 121078-34-0 C13H14O2
—— (4R,5R)-(-)-5-[(1Z)-1-iodo-1-butenyl]-4-methyl-4,5-dihydo-2-(3H)-furanone 1215224-23-9 C9H13IO2
—— (1S,3R,4S,6R)-4-(tert-butyldimethylsiloxy)-6-chloro-1-hydroxy-5-oxocyclohexane-1,3-carbolactone 863983-55-5 C13H21ClO5Si
—— 56948-59-5 C18H22O4
—— (4aR,5R)-5-(2-Iodo-ethyl)-6-methoxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one 54867-40-2 C11H15IO4
—— 3-<i>tert</i>-butyl-3,4,4-trimethyl-oxetan-2-one 30436-15-8 C10H18O2
—— 57199-28-7 C12H13ClO4
—— (1R,3S,6R,7S,9R)-7-Ethyl-5-oxo-4-oxa-tricyclo[4.2.1.0<sup>3,7</sup>]nonane-9-carboxylic acid methyl ester 57199-43-6 C12H16O4
—— 66389-14-8 C14H18O4
—— (4E)-(1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-4-[3'-hydroxypropylidene]-6-oxabicyclo[3.2.1]octan-7-one 960501-70-6 C18H30O6Si
—— 59441-79-1 C15H16O4
—— 2-Methyl-2-propanyl 2,2-dimethyl-4-({5-oxo-3,4-bis[(trimethylsily l)oxy]tetrahydro-2-furanyl}[(trimethylsilyl)oxy]methyl)-1,3-oxazo lidine-3-carboxylate (non-preferred name) 136597-85-8 C24H49NO8Si3
—— (Z)-(3S,3aR,9aS)-2-Oxo-2,3,3a,4,5,8,9,9a-octahydro-cycloocta[b]furan-3-carboxylic acid methyl ester 56695-25-1 C12H16O4
—— exo,exo-9,11-Bis-(1,3-dioxa-2-cyclopentyl)-3,6-dioxabicyclo<6.3.0>undecan-2,7-dion 59543-23-6 C15H20O8
—— 2-Phenyl-1,3-dioxolo<4,5-f>perhydroisobenzofuran-5-on 124804-06-4 C15H16O4
—— 5,6-dimethyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one 57741-48-7 C10H14O2