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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
—— (3R,5S,6S)-tetrahydro-6-<(1S,2S,3R)-2-hydroxy-1,3-dimethyl-4-pentenyl>-3,5-dimethyl-2H-pyran-2-one 120742-72-5 C14H24O3
—— [(3aS,6R,8aR)-2-oxo-3,3a,4,5,6,8a-hexahydrocyclohepta[b]furan-6-yl] acetate 121724-54-7 C11H14O4
—— (4S,4'S,7R,7'R)-4,4'-[oxybis(propane-2,2-diyl)]bis(7-methyloxepan-2-one) 1408324-06-0 C20H34O5
—— (+/-)-nor-sterepolide 104476-84-8 C13H12O4
—— 81309-73-1 C14H20O3
—— 4,5-dihydro-3-fluoro-5-(iodomethyl)-4-methyl-2(3H)-furanone 98064-47-2 C6H8FIO2
—— <i>rac</i>-3,3-ethanediyldioxy-16-ethoxy-11β,14-dihydroxy-16,17-seco-14α-pregna-5,20-dien-15-yn-18-oic acid-11-lactone 124383-08-0 C25H32O6
—— 6(R)-[2-[8(S)-(2,2-Dimethylbutyryloxy)-2(S)-methyl-6(R)-hydroxymethyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one 131564-92-6 C25H42O6
—— (3R,5S)-3-((E)-6-hydroxyhexyl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one 1601468-21-6 C11H20O4
—— 3-Vinyl-1,2-dichlor-cyclobutan-1,2-dicarbonsaeure-anhydrid 122675-48-3 C8H6Cl2O3
—— (R)-5-((S)-2-methyl-2-(trimethylsilyloxy)penta-3,4-dienyl)dihydrofuran-2(3H)-one 1440533-43-6 C13H22O3Si
—— diisopropyl-4,4 oxa-3 bicyclo<3.2.0>heptanone-2 97181-69-6 C12H20O2
—— 4,5,12,13-Tetrabromo-8,16-dimethyl-1,9-dioxacyclohexadecane-2,10-dione 80708-17-4 C16H24Br4O4
—— 5-(bromo(cyclohexyl)methyl)dihydrofuran-2(3H)-one 1379786-25-0 C11H17BrO2
—— 2-oxatricyclo<4.2.1.0<sup>4,9</sup>>nonan-3-one 23783-85-9 C8H10O2
—— (4R)-4-phenyl-6-methylidenetetrahydro-2-pyranone 122019-97-0 C12H12O2
—— 2-methyl-3-trifluoromethylglutaric acid anhydride 138500-81-9 C7H7F3O3
—— cis-anti-cis-5,5,8,8-tetramethyl-4,9-dioxatricyclo(5.3.0.0<sup>2,6</sup>)decane-3,10-dione 87325-05-1 C12H16O4
—— (3S,4S)-4,5-dihydroxy-3-isopropenylpentanoic acid γ-lactone 108404-52-0 C8H12O3
—— (S)-2-{(2R,3S,5S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-6-oxo-tetrahydro-pyran-2-yl}-propionaldehyde 82830-78-2 C27H36O4Si
—— (R)-5-((S)-3-oxocyclohexyl)dihydrofuran-2(3H)-one 1425314-27-7 C10H14O3
—— 4,4-Dimethyl-3-[1-triethylsilanyl-meth-(Z)-ylidene]-oxetan-2-one 128549-42-8 C12H22O2Si
—— ethyl (3S,4R)-(-)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate 869594-37-6 C8H12O4
—— (3R,4R,5R)-3,5-dimethyl-4-phenyloxolan-2-one 1402922-07-9 C12H14O2
—— (5S,6S)-6-[(E)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propenyl]-9-[1-butylsulfanyl-meth-(E)-ylidene]-4-methoxy-1-oxa-spiro[4.5]dec-3-ene-2,8-dione 123719-31-3 C35H44O5SSi
—— 7-phenyl-6-oxaspiro[3.4]octane-5,8-dione 97610-50-9 C13H12O3
—— 5(R)-bromo-6-cyclopentyl-2(S)-isopropyl-4(S)-hexanolide 118041-15-9 C14H23BrO2
—— rac-(3aR,4R,5S,6aS)-4-((chloro(methyl)amino)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 75283-78-2 C9H14ClNO3
—— 6(R)-[2-[8(S)-(2,2 dimethylbutyryloxy)-2(S),4(R),6(S)-trimethyl-4-hydroxy-1,2,3,4,4a(S),5,6,7,8,8a(R)-decahydronaphthyl-1(S)]ethyl]-4(R)-(t-butyldimethylsilyloxy)-3,4,5,6,-tetrahydro-pyran-2-one 132395-25-6 C32H58O6Si
—— 4-methoxy-6-pentadecyltetrahydro-2H-pyran-2-one 1206482-63-4 C21H40O3
—— Buta-2,3-dienoic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 125812-34-2 C10H12O4
—— (1R,2S,5S,6R,7S)-5-[3-(Z)-pentenyl]-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 662112-04-1 C14H18O2
—— (1R,2S,5S,6R,7S)-5-[3-(E)-pentenyl]-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 662112-15-4 C14H18O2
—— 86971-97-3 C17H24O5
—— cis-1-(methoxymethoxy)-9-methylene-7-oxabicyclo<4.3.0>nonan-8-one 116608-66-3 C11H16O4
—— 2a,5a,7-trimethyl-octahydro-naphtho[1,8-<i>bc</i>]furan-2,6-dione 107910-98-5 C14H20O3
—— 3-(1-Methoxy-3-phenyl-propyl)-dihydro-furan-2-one 60669-61-6 C14H18O3
—— 6(R)-[2-[8(S)-(2,2-Dimethylbutyryloxy)-2(S)-methyl-6(R)-formyl-1,2,3,4,4a(s),5,6,7,8,8a(s)-decahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one 114883-33-9 C25H40O6
—— 9-methyl-1-oxaspiro[4.5]decane-2,6-dione 5898-89-5 C10H14O3
—— 2-OXASPIRO[5.7]TRIDECAN-3-ONE 465533-25-9 C12H20O2
—— 5-(1-Chloro-2-methyl-propenyl)-3,3-diethyl-dihydro-furan-2-one 100090-24-2 C12H19ClO2
—— 1-Oxo-eudesmadien-(3.8)-olid-(6.12) 108299-29-2 C15H18O3
—— (1S,6S)-5-Hydroxy-1-(2-hydroxy-4,4-dimethyl-cyclopentyl)-5-methyl-3-oxa-bicyclo[4.2.0]octan-4-one 73879-80-8 C15H24O4
—— 1402922-20-6 C13H18O2
—— 4,4-Dimethyl-3-(3-methylbut-1-enyl)butanolide 27373-86-0 C11H18O2
—— (5R,6R)-6-hydroxy-6-methyl-8-methylidene-2-oxaspiro[4.5]decan-1-one 91781-85-0 C11H16O3
—— 2-[(E)-2-(benzyloxymethoxy)methyl-1-propenyl]-4H-oxazol-5-one 205441-77-6 C15H17NO4
—— (R)-6-[(S)-1,2-bis(triethylsiloxy)ethyl]-6-butyltetrahydro-2H-pyran-2-one 1097690-20-4 C23H48O4Si2
—— (R)-4-Hydroxy-5-(iodo-trimethylsilanyl-methyl)-dihydro-furan-2-one 128855-27-6 C8H15IO3Si
—— 2(3H)-Furanone, dihydro-3-mercapto-4-(1-methylethenyl)-, cis- 118887-82-4 C7H10O2S