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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-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one —— C10H16O3
8-Hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one
—— 1-(4-methyl-1-pentanoyl)-3-oxabicyclo[3.1.0]hexan-2-one —— C11H16O3
1-(4-methyl-1-pentanoyl)-3-oxabicyclo[3.1.0]hexan-2-one
—— 9-ethenyl-8-hydroxy-5,5,9,11b-tetramethyl-2,5a,6,7,8,10-hexahydro-1H-benzo[g][2]benzoxepine-3,11-dione —— C20H28O4
9-ethenyl-8-hydroxy-5,5,9,11b-tetramethyl-2,5a,6,7,8,10-hexahydro-1H-benzo[g][2]benzoxepine-3,11-dione
—— 9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione —— C15H16O4
9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
—— 6-[2-Hydroxy-5-(2-methyl-5-oxooxolan-2-yl)pent-4-en-2-yl]-3-methylidene-4-(3-oxobutyl)oxan-2-one —— C20H28O6
6-[2-Hydroxy-5-(2-methyl-5-oxooxolan-2-yl)pent-4-en-2-yl]-3-methylidene-4-(3-oxobutyl)oxan-2-one
—— 2-[5-(Furan-3-yl)-2-oxooxolan-3-ylidene]-10,12-dihydroxy-12-methyl-8-oxatricyclo[4.3.3.01,6]dodecan-7-one —— C20H22O7
2-[5-(Furan-3-yl)-2-oxooxolan-3-ylidene]-10,12-dihydroxy-12-methyl-8-oxatricyclo[4.3.3.01,6]dodecan-7-one
—— 2,6,15,16,19-Pentamethyl-5-prop-1-en-2-yl-10-oxahexacyclo[11.8.1.12,6.01,13.014,19.011,23]tricosan-9-one —— C30H46O2
2,6,15,16,19-Pentamethyl-5-prop-1-en-2-yl-10-oxahexacyclo[11.8.1.12,6.01,13.014,19.011,23]tricosan-9-one
—— [2-(Hydroxymethyl)-7-(methoxymethyl)-11-methyl-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-dien-9-yl] 2-methylprop-2-enoate —— C20H24O8
[2-(Hydroxymethyl)-7-(methoxymethyl)-11-methyl-6,12-dioxo-5,14-dioxatricyclo[9.2.1.04,8]tetradeca-1(13),2-dien-9-yl] 2-methylprop-2-enoate
—— 3-Hexadecylidene-4,5-dihydroxy-5-methyloxolan-2-one —— C21H38O4
3-Hexadecylidene-4,5-dihydroxy-5-methyloxolan-2-one
—— Icetexone 276890-94-9 C20H22O5
Icetexone
—— (5-Hydroxy-5,9-dimethyl-3-methylidene-2,8-dioxo-3a,4,11,11a-tetrahydrocyclodeca[b]furan-4-yl) 2-methylpropanoate —— C19H24O6
(5-Hydroxy-5,9-dimethyl-3-methylidene-2,8-dioxo-3a,4,11,11a-tetrahydrocyclodeca[b]furan-4-yl) 2-methylpropanoate
—— 5-ethyl-3-hexadecoxy-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one —— C24H43O6P
5-ethyl-3-hexadecoxy-3-oxo-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one
—— [13-(Furan-3-yl)-7-hydroxy-6,6,10-trimethyl-15-oxo-2,14-dioxatricyclo[9.4.0.01,3]pentadecan-8-yl] 2-methylbut-2-enoate —— C25H34O7
[13-(Furan-3-yl)-7-hydroxy-6,6,10-trimethyl-15-oxo-2,14-dioxatricyclo[9.4.0.01,3]pentadecan-8-yl] 2-methylbut-2-enoate
—— (9-formyl-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl) 2-methylprop-2-enoate —— C19H18O6
(9-formyl-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl) 2-methylprop-2-enoate
—— 4-Hydroxy-5-methyl-3-(19-phenylnonadecyl)oxolan-2-one —— C30H50O3
4-Hydroxy-5-methyl-3-(19-phenylnonadecyl)oxolan-2-one
—— Methyl 2-[13-(furan-3-yl)-1,3-dihydroxy-4,6,14-trimethyl-7,11-dioxo-9,12-dioxahexacyclo[8.7.1.13,6.02,8.04,17.014,18]nonadecan-5-yl]acetate —— C27H32O9
Methyl 2-[13-(furan-3-yl)-1,3-dihydroxy-4,6,14-trimethyl-7,11-dioxo-9,12-dioxahexacyclo[8.7.1.13,6.02,8.04,17.014,18]nonadecan-5-yl]acetate
—— 5-(1-Hydroxyoctylidene)-4,6-dioxooxane-2-carboxylic acid —— C14H20O6
5-(1-Hydroxyoctylidene)-4,6-dioxooxane-2-carboxylic acid
—— 3-Decylidene-4,5-dihydroxy-5-methyloxolan-2-one —— C15H26O4
3-Decylidene-4,5-dihydroxy-5-methyloxolan-2-one
—— (15-Hydroxy-6-methylidene-5-oxo-4,14,16-trioxatetracyclo[8.4.3.01,13.03,7]heptadec-9-en-8-yl) 2-methylpropanoate 21871-14-7 C19H24O7
(15-Hydroxy-6-methylidene-5-oxo-4,14,16-trioxatetracyclo[8.4.3.01,13.03,7]heptadec-9-en-8-yl) 2-methylpropanoate
—— 3-Hydroxy-4-(hydroxymethyl)-3-[3-(3-methyloxiran-2-yl)prop-2-enoyl]oxolan-2-one —— C11H14O6
3-Hydroxy-4-(hydroxymethyl)-3-[3-(3-methyloxiran-2-yl)prop-2-enoyl]oxolan-2-one
—— Methyl 5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.01,14.04,9]heptadecane-13-carboxylate —— C21H32O4
Methyl 5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.01,14.04,9]heptadecane-13-carboxylate
—— 16-(Furan-3-yl)-5-hydroxy-2,6,6,11,17-pentamethyl-10,15-dioxatetracyclo[9.8.0.02,7.012,17]nonadeca-3,12-diene-9,14-dione —— C26H32O6
16-(Furan-3-yl)-5-hydroxy-2,6,6,11,17-pentamethyl-10,15-dioxatetracyclo[9.8.0.02,7.012,17]nonadeca-3,12-diene-9,14-dione
—— 7-Hydroxy-2,6,6,9-tetramethyl-11-oxatricyclo[5.5.0.02,10]dodec-8-en-12-one —— C15H22O3
7-Hydroxy-2,6,6,9-tetramethyl-11-oxatricyclo[5.5.0.02,10]dodec-8-en-12-one
—— 5-(2-methylpropyl)-3-oxo-3-tridecoxy-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one —— C23H41O6P
5-(2-methylpropyl)-3-oxo-3-tridecoxy-8,8a-dihydro-1H-furo[3,4-e][1,3,2]dioxaphosphepin-6-one
—— 2,7,8-Trihydroxy-6-(hydroxymethyl)-7,13-dimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one —— C15H22O7
2,7,8-Trihydroxy-6-(hydroxymethyl)-7,13-dimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one
—— 3-Oxo-2,11-dioxatricyclo[5.4.0.04,8]undeca-5,9-diene-10-carboxamide —— C10H9NO4
3-Oxo-2,11-dioxatricyclo[5.4.0.04,8]undeca-5,9-diene-10-carboxamide
—— 3,6,9-Trimethyl-3,3a,4,5,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione —— C15H20O3
3,6,9-Trimethyl-3,3a,4,5,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione
—— 17-(Furan-3-yl)-2,7,7,18-tetramethyl-6,9,16-trioxapentacyclo[11.7.0.02,8.08,10.014,18]icosa-3,12-diene-5,11,15-trione —— C25H26O7
17-(Furan-3-yl)-2,7,7,18-tetramethyl-6,9,16-trioxapentacyclo[11.7.0.02,8.08,10.014,18]icosa-3,12-diene-5,11,15-trione
—— 11,13-Dihydropsilotropin 26931-86-2 C15H22O4
11,13-Dihydropsilotropin
—— 2-(1,2-Dimethyl-9-methylidene-6-oxo-5-oxatricyclo[5.2.2.04,8]undecan-7-yl)acetaldehyde —— C15H20O3
2-(1,2-Dimethyl-9-methylidene-6-oxo-5-oxatricyclo[5.2.2.04,8]undecan-7-yl)acetaldehyde
—— 3'-Hydroxy-13-methylspiro[15-oxatetracyclo[11.2.1.01,10.04,9]hexadecane-5,4'-oxolane]-2',14-dione —— C19H26O5
3'-Hydroxy-13-methylspiro[15-oxatetracyclo[11.2.1.01,10.04,9]hexadecane-5,4'-oxolane]-2',14-dione
—— 7,8,13,14-Tetrahydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one —— C15H22O7
7,8,13,14-Tetrahydroxy-6,7,13-trimethyl-4,9-dioxatetracyclo[6.5.1.01,10.06,10]tetradecan-3-one
—— (13-Hydroxy-6-methyl-17,18-dioxo-16-oxatetracyclo[13.2.2.03,11.04,8]nonadeca-1,9-dien-7-yl) 2-methylpropanoate —— C23H30O6
(13-Hydroxy-6-methyl-17,18-dioxo-16-oxatetracyclo[13.2.2.03,11.04,8]nonadeca-1,9-dien-7-yl) 2-methylpropanoate
—— 9-Ethenyl-9-methyl-2-propan-2-yl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione —— C13H16O4
9-Ethenyl-9-methyl-2-propan-2-yl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione
—— 5-Decyl-3-[2,3-di(propan-2-yloxy)propyl]oxolan-2-one —— C23H44O4
5-Decyl-3-[2,3-di(propan-2-yloxy)propyl]oxolan-2-one
—— 2,17-Dihydroxy-10,10-dimethyl-3-methylidene-7,14-dioxapentacyclo[7.6.2.11,4.06,16.013,17]octadecane-8,15-dione —— C19H24O6
2,17-Dihydroxy-10,10-dimethyl-3-methylidene-7,14-dioxapentacyclo[7.6.2.11,4.06,16.013,17]octadecane-8,15-dione
—— 5-(10,10-Dibromo-3-hydroxydeca-1,9-dienyl)oxolan-2-one —— C14H20Br2O3
5-(10,10-Dibromo-3-hydroxydeca-1,9-dienyl)oxolan-2-one
—— (8-hydroxy-5,8-dimethyl-1-methylidene-2-oxo-4,5,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-6-yl) acetate —— C17H22O5
(8-hydroxy-5,8-dimethyl-1-methylidene-2-oxo-4,5,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-6-yl) acetate
—— 7,10-Dimethyl-3-methylidene-3a,4,5,6,9,11a-hexahydrocyclodeca[b]furan-2-one —— C15H20O2
7,10-Dimethyl-3-methylidene-3a,4,5,6,9,11a-hexahydrocyclodeca[b]furan-2-one
—— 3-Hydroxy-16-[1-(3-hydroxy-5-methyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.03,9.013,17]nonadec-1(12)-en-6-one —— C30H44O6
3-Hydroxy-16-[1-(3-hydroxy-5-methyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.03,9.013,17]nonadec-1(12)-en-6-one
—— 5,7a-Dihydroxy-3-methyl-3,4,4a,5,6,7-hexahydrocyclopenta[c]pyran-1-one —— C9H14O4
5,7a-Dihydroxy-3-methyl-3,4,4a,5,6,7-hexahydrocyclopenta[c]pyran-1-one
—— 6-hepta-1,3-dienyl-3a,4-dihydroxy-4,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-3-one —— C14H20O4
6-hepta-1,3-dienyl-3a,4-dihydroxy-4,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-3-one
—— Methyl 2-(12-hydroxy-12-methyl-7,10,16-trioxo-2,15,18-trioxatetracyclo[7.7.2.01,3.014,17]octadecan-5-yl)prop-2-enoate —— C20H24O9
Methyl 2-(12-hydroxy-12-methyl-7,10,16-trioxo-2,15,18-trioxatetracyclo[7.7.2.01,3.014,17]octadecan-5-yl)prop-2-enoate
—— 4-Hydroxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.01,3.04,8]tridec-9-en-13-one —— C15H20O3
4-Hydroxy-3,6,6-trimethyl-12-oxatetracyclo[8.3.0.01,3.04,8]tridec-9-en-13-one
—— 6-Hydroxy-1-trideca-1,4,7,10-tetraenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-3-one —— C20H28O3
6-Hydroxy-1-trideca-1,4,7,10-tetraenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-3-one
—— 5-Heptadec-13-enyl-4-hydroxy-3-(hydroxymethyl)-5-methyloxolan-2-one —— C23H42O4
5-Heptadec-13-enyl-4-hydroxy-3-(hydroxymethyl)-5-methyloxolan-2-one
—— 4-(1-Hydroxy-3,3-dimethylbutyl)-3-methylideneoxolan-2-one —— C11H18O3
4-(1-Hydroxy-3,3-dimethylbutyl)-3-methylideneoxolan-2-one
—— (14-Hydroperoxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadecan-4-yl) butanoate —— C24H36O7
(14-Hydroperoxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadecan-4-yl) butanoate
—— 13-Methylspiro[15-oxatetracyclo[11.2.1.01,10.04,9]hexadecane-5,4'-oxolane]-2',14-dione 120216-78-6 C19H26O4
13-Methylspiro[15-oxatetracyclo[11.2.1.01,10.04,9]hexadecane-5,4'-oxolane]-2',14-dione
—— (5-ethylidene-2-oxotetrahydropyran-4-yl)acetic acid 38164-97-5 C9H12O4
(5-ethylidene-2-oxotetrahydropyran-4-yl)acetic acid