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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
—— 1432321-08-8 C13H14O3
—— γ-2-(methoxyethoxy)-ε-caprolactone 1493900-34-7 C9H16O4
—— (3R,3aR,4S,6aR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one 909911-56-4 C16H30O5Si
—— trans,cis-2-methyl-3-hydroxy-4-(iodomethyl)-γ-bytyrolactone 86390-90-1 C6H9IO3
—— (3aR,4S,6R,6aR)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one 620114-86-5 C31H43IO3Si
—— xestospongiene K 1263368-20-2 C14H20Br2O3
—— 2-(1-hydroxy-1-methylheptyl)butanolide 78344-39-5 C12H22O3
—— 2-Allyl-5-oxo-2-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 344869-81-4 C16H18O4
—— 8a-(5-Methyl-furan-2-yl)-octahydro-chromen-2-one 103560-29-8 C14H18O3
—— (2aR,5aR,8aS,8bR)-8b-Hydroxymethyl-7,7-dimethyl-octahydro-5-oxa-cyclobuta[e]azulene-1,4-dione 79745-93-0 C14H20O4
—— 3-Ethyl-4-methyl-5-vinyl-dihydro-furan-2-one 87441-59-6 C9H14O2
—— 3-((2S,3S)-3-((tert-butyldiphenylsilyl)oxy)-5-oxotetrahydrofuran-2-yl)propanal 1110638-63-5 C23H28O4Si
—— (R)-6-ethyltetrahydropyran-2-one 108943-43-7 C7H12O2
—— 5-<i>tert</i>-butyl-3-methyl-furan-2,4-dione 100144-98-7 C9H14O3
—— (3aS,6aS,1'R,2'R,5'R)-4-<<2'-(1''-methylethenyl)-5'-methylcyclopentyl>methyl>-4-(methoxymethyl)-2,3,3a,4-tetrahydro-6aH-cyclopenta<b>furan-2-one 133349-36-7 C19H28O3
—— 1,7-dioxa-dispiro[4.0.4.2]dodecane-2,8-dione 92315-70-3 C10H12O4
—— (2S,2'R,5'S)-5'-Bromomethyl-5'-hydroxy-2-methyl-tetrahydro-[2,2']bifuranyl-5-one 79756-31-3 C10H15BrO4
—— cis-Hydroxy-cycloheptylessigsaeurelacton 156406-73-4 C9H14O2
—— (3R,4R)-tetrahydro-4-(2-cyanoethyl)-4-methyl-5-methylene-2-oxo-3-furanacetic acid methyl ester 1035970-83-2 C12H15NO4
—— Acetic acid (R)-2-methyl-1-((S)-4-methylene-5-oxo-tetrahydro-furan-2-ylmethyl)-propyl ester 139926-73-1 C12H18O4
—— 13-acetoxy-7α-hydroxy-17-norlabdan-8,9-olide 121045-97-4 C21H36O5
—— (3S,5R)-3-benzyl-dihydro-5-phenylfuran-2(3H)-one 176198-85-9 C17H16O2
—— (R)-6-[(1E,3Z,7E,9E)-(5R,14R)-14-(tert-Butyl-dimethyl-silanyloxy)-3-ethyl-12-hydroxy-5,9-dimethyl-heptadeca-1,3,7,9-tetraenyl]-5,6-dihydro-pyran-2-one 331814-97-2 C32H54O4Si
—— rel-(4R,5S)-dihydro-4-hydroxy-5-(iodomethyl)-4-methyl-2(3H)-furanone 86335-97-9 C6H9IO3
—— (2aα,4aα,5α,5aβ,7α,9bR*,9cα,10aα)-(+/-)-7-ethenyl-1,2,2a,4a,5,5a,6,7,8,9c,10,10a-dodecahydro-5-hydroxy-2a,7-dimethyl-3H-cyclopropa<4,4a>phenanthro<10,1-bc>furan-3-one 143495-32-3 C20H26O3
—— 7,9A-dimethyl-hexahydro-cyclohepta[1,2-<i>b</i>;4,5-<i>b'</i>]difuran-2,4,6-trione 109129-39-7 C13H16O5
—— (2aα,5β,6aβ,7aβ,7bα,7cα)-(+/-)-6-ethenyl-2a,3,4,5,6a,7a,7b,7c-octahydro-5-(hydroxymethyl)-2a-methyl-2H-oxireno<2,3>naphtho<1,8-bc>furan-2-one 143495-23-2 C15H18O4
—— 5R-(1R-hydroxy-6-trimethylsilylhex-5-ynyl)dihydrofuran-2-one 866885-74-7 C13H22O3Si
—— (5S)-5-tert-butyldimethylsilyloxymethyl-5-tetradecanolide 75989-78-5 C21H42O3Si
—— (1-Methyl-3-hydroxy-n-butyl)-malonester-δ-lacton 19823-31-5 C10H16O4
—— (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)methyl-2-hydroxy-3-methylbutyrolactone 197777-39-2 C12H24O4Si
—— 5,5-dimethyl-3-propionyl-3-(thiophen-2-yl)dihydrofuran-2(3H)-one 1342897-36-2 C13H16O3S
—— 8α-acetoxyachillin 35866-60-5 C17H20O5
—— 1039627-80-9 C12H12Br4O5
—— tert-butyl ((1S,5S,6R)-1-butyl-2-oxo-3-oxabicyclo[4.1.0]heptan-5-yl)carbamate 1431611-28-7 C15H25NO4
—— 3-Chloro-5-decyl-dihydro-furan-2-one 272781-71-2 C14H25ClO2
—— (1SR,5RS)-1-(5-bromo-2-fluoro-phenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one 1346146-38-0 C11H8BrFO2
—— (1S,2S,3R,5R)-ethyl-5-(2-hydroxypropan-2-yl)-7-oxo-2-phenyl-6-oxabicyclo[3.2.0]heptane-3-carboxylate 1111644-50-8 C18H22O5
—— 6,6-dimethyl-4-isopropoxy-3-oxa-bicyclo[3,1,0]hexan-2-one 101757-10-2 C10H16O3
—— trans-5-cyclohexyl-3-methyldihydrofuran-2(3H)-one 128756-48-9 C11H18O2
—— opt. inakt. 4-Ethoxy-4-hydroxy-2-propyl-buttersaeure-lacton 3601-52-3 C9H16O3
—— 3-benzyltetrahydro-2H-pyran-2-one 68975-22-4 C12H14O2
—— <(2R)-2r,4c-Dihydroxy-2.6.6-trimethyl-cyclohexyl>-essigsaeure-2-lacton 1133-01-3 C11H18O3
—— (1S,3R,5R)-3-(tert-butyldimethylsilyloxy)-6-oxabicyclo[3.2.0]heptan-7-one 1242309-72-3 C12H22O3Si
—— (1RS,2SR,6SR)-1,2-dichloro-9-oxo-8-oxabicyclo<4.3.0>non-4-ene-2-carboxylic acid 103723-28-0 C9H8Cl2O4
—— 1360818-21-8 C27H52O6Si2
—— (S)-3-isopropyl-4-(2-methylpropylidene)oxetan-2-one 935473-94-2 C10H16O2
—— 1217293-35-0 C17H24O2
—— cis-2-allyl-3-methyl-2-vinyl-5-pentanolide 114199-55-2 C11H16O2
—— 1,7-dioxa-2,8-dioxo-3,9-dimethylene cyclododecane 132841-92-0 C12H16O4