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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
—— 8-Hydroxy-8,14-dimethyl-2-oxatetracyclo[9.2.1.04,13.07,12]tetradec-4-en-3-one —— C15H20O3
8-Hydroxy-8,14-dimethyl-2-oxatetracyclo[9.2.1.04,13.07,12]tetradec-4-en-3-one
—— 3-Dodec-1-enyl-4-hydroxy-5-methyloxolan-2-one —— C17H30O3
3-Dodec-1-enyl-4-hydroxy-5-methyloxolan-2-one
—— 10-Hydroxy-4,5,9,9,13-pentamethyl-20-oxahexacyclo[17.2.2.01,18.04,17.05,14.08,13]tricosan-21-one —— C27H42O3
10-Hydroxy-4,5,9,9,13-pentamethyl-20-oxahexacyclo[17.2.2.01,18.04,17.05,14.08,13]tricosan-21-one
—— (11-Oxo-4-tridecyl-5,7-dioxadispiro[5.1.58.26]pentadeca-9,12-dien-2-yl) 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate —— C36H54O7
(11-Oxo-4-tridecyl-5,7-dioxadispiro[5.1.58.26]pentadeca-9,12-dien-2-yl) 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
—— (2'-Formyl-7-hydroxy-1'-methyl-10-methylidene-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,3'-cyclohexane]-1'-yl) acetate —— C21H26O7
(2'-Formyl-7-hydroxy-1'-methyl-10-methylidene-2,11-dioxospiro[3-oxatricyclo[7.2.1.01,6]dodecane-5,3'-cyclohexane]-1'-yl) acetate
—— Methyl 2,5,6-trimethyl-8-oxo-1,7-dioxaspiro[2.5]octane-6-carboxylate —— C11H16O5
Methyl 2,5,6-trimethyl-8-oxo-1,7-dioxaspiro[2.5]octane-6-carboxylate
—— 3-Hexadeca-9,11,15-trien-7-ynyl-4-hydroxy-5-methyloxolan-2-one —— C21H30O3
3-Hexadeca-9,11,15-trien-7-ynyl-4-hydroxy-5-methyloxolan-2-one
—— 4-Hydroxy-3,7-dimethyl-14-methylidene-15-oxo-16-oxatetracyclo[11.3.1.02,11.03,8]heptadec-2(11)-ene-7-carboxylic acid —— C20H26O5
4-Hydroxy-3,7-dimethyl-14-methylidene-15-oxo-16-oxatetracyclo[11.3.1.02,11.03,8]heptadec-2(11)-ene-7-carboxylic acid
—— 3-(8-Chloro-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluorooctyl)oxan-2-one —— C13H7ClF16O2
3-(8-Chloro-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluorooctyl)oxan-2-one
—— 5-Pentacosyloxolan-2-one —— C29H56O2
5-Pentacosyloxolan-2-one
—— 4-Hydroxy-5-(1-hydroxyethyl)-3-(2-hydroxypropylidene)oxolan-2-one —— C9H14O5
4-Hydroxy-5-(1-hydroxyethyl)-3-(2-hydroxypropylidene)oxolan-2-one
—— 5-(10,10-Dibromo-1-methoxydeca-2,9-dienyl)oxolan-2-one —— C15H22Br2O3
5-(10,10-Dibromo-1-methoxydeca-2,9-dienyl)oxolan-2-one
—— 10,11-Dihydroxy-4,5,13,19,20-pentamethyl-9-methylidene-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-23-one —— C29H42O4
10,11-Dihydroxy-4,5,13,19,20-pentamethyl-9-methylidene-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-23-one
—— 5'-(Furan-3-yl)-11-hydroxy-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4(12)-ene-9,3'-oxolane]-2',3-dione —— C19H20O6
5'-(Furan-3-yl)-11-hydroxy-10-methylspiro[2-oxatricyclo[6.3.1.04,12]dodec-4(12)-ene-9,3'-oxolane]-2',3-dione
—— 5-(5-Hydroxy-2-methyl-3-oxocyclopenten-1-yl)-3-methylidene-4-(3-oxobutyl)oxolan-2-one —— C15H18O5
5-(5-Hydroxy-2-methyl-3-oxocyclopenten-1-yl)-3-methylidene-4-(3-oxobutyl)oxolan-2-one
—— (8-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-4-yl) 2-methylprop-2-enoate —— C18H22O5
(8-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-4-yl) 2-methylprop-2-enoate
—— 9-(hydroxymethyl)-4-[[9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl]oxy]-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione —— C30H32O9
9-(hydroxymethyl)-4-[[9-(hydroxymethyl)-3,6-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl]oxy]-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
—— 16-(Dimethylamino)-6,13-dimethyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-8-one —— C23H35NO2
16-(Dimethylamino)-6,13-dimethyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-18-en-8-one