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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
—— 3-oxaglutaric anhydride 63408-11-7 C5H4O4
3-oxaglutaric anhydride
—— (3S,4S)-3-Chloro-4-chloromethyl-dihydro-furan-2-one 124224-44-8 C5H6Cl2O2
(3S,4S)-3-Chloro-4-chloromethyl-dihydro-furan-2-one
—— (3S,4R)-3-Chloro-4-chloromethyl-dihydro-furan-2-one 124224-42-6 C5H6Cl2O2
(3S,4R)-3-Chloro-4-chloromethyl-dihydro-furan-2-one
—— 1-Methyl-6-oxabicyclo[3.2.1]octane-7,8-dione 91086-69-0 C8H10O3
1-Methyl-6-oxabicyclo[3.2.1]octane-7,8-dione
—— (R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4R)-phenyldihydrofuran-2-one 737783-21-0 C25H31BrO2
(R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4R)-phenyldihydrofuran-2-one
—— (4R,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one 737782-86-4 C21H31BrO2
(4R,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one
—— (4R,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one 737782-98-8 C23H35BrO2
(4R,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one
—— (4S,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one 737783-20-9 C23H35BrO2
(4S,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one
—— (4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one 737782-99-9 C23H35BrO2
(4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one
—— (S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-3-methylenedihydrofuran-2-one 173388-43-7 C19H27BrO2
(S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-3-methylenedihydrofuran-2-one
—— (4R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one 737782-92-2 C21H31BrO2
(4R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one
—— (R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4S)-phenyldihydrofuran-2-one 737783-30-1 C25H31BrO2
(R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4S)-phenyldihydrofuran-2-one
—— (S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-4,4-dimethyl-3-methylenedihydrofuran-2-one 737783-34-5 C21H31BrO2
(S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-4,4-dimethyl-3-methylenedihydrofuran-2-one
—— (4R,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one 737783-10-7 C23H35BrO2
(4R,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one
—— (4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-propyloxolan-2-one 917805-09-5 C22H33BrO2
(4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-propyloxolan-2-one
—— (S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4R)-phenyldihydrofuran-2-one 737783-26-5 C25H31BrO2
(S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4R)-phenyldihydrofuran-2-one
—— (4R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one 737783-04-9 C23H35BrO2
(4R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one
—— (4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one 737783-11-8 C23H35BrO2
(4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one
—— (4R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one 737783-15-2 C23H35BrO2
(4R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylidene-4-(2-methylpropyl)oxolan-2-one
—— (S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4S)-phenyldihydrofuran-2-one 737783-22-1 C25H31BrO2
(S)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroindene-1-yl]propyl}-3-methylene-(4S)-phenyldihydrofuran-2-one
—— (4S,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one 737783-09-4 C23H35BrO2
(4S,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-butyl-3-methylideneoxolan-2-one
—— (R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-4,4-dimethyl-3-methylenedihydrofuran-2-one 737783-31-2 C21H31BrO2
(R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-4,4-dimethyl-3-methylenedihydrofuran-2-one
—— (4S,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one 737782-97-7 C21H31BrO2
(4S,5R)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one
—— (4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one 737782-87-5 C21H31BrO2
(4S,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-4-ethyl-3-methylideneoxolan-2-one
—— (R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-3-methylenedihydrofuran-2-one 173522-65-1 C19H27BrO2
(R)-5-{(R)-2-[(1R,4E,3aR,7aR)-4-bromomethylene-7a-methylperhydroinden-1-yl]propyl}-3-methylenedihydrofuran-2-one
—— (4R,5R)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one 639460-28-9 C20H29BrO2
(4R,5R)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one
—— (4S,5S)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one 639460-27-8 C20H29BrO2
(4S,5S)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one
—— (4S,5R)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one 639460-31-4 C20H29BrO2
(4S,5R)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one
—— (4R,5S)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one 639460-33-6 C20H29BrO2
(4R,5S)-5-((R)-2-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-4-methyl-3-methylene-dihydro-furan-2-one
—— 3-ethyl-5-isopropyl-dihydro-furan-2-one 121725-95-9 C9H16O2
3-ethyl-5-isopropyl-dihydro-furan-2-one
—— [(3S,3aS,8S,9aR,9bS)-3,6-dimethyl-9-methylidene-2-oxo-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] acetate 82263-14-7 C17H22O4
[(3S,3aS,8S,9aR,9bS)-3,6-dimethyl-9-methylidene-2-oxo-3,3a,4,5,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] acetate
—— β-octanolactone 28859-23-6 C8H14O2
β-octanolactone
—— (3E,8E)-4,8-dimethyl-3,8-decadien-10-olide 111351-08-7 C12H18O2
(3E,8E)-4,8-dimethyl-3,8-decadien-10-olide
—— 6-(1,1-dimethylethoxy)-5-methylsulfonyloxy-4,4-dimethyl-tetrahydro-pyr-2-one 118528-20-4 C12H22O6S
6-(1,1-dimethylethoxy)-5-methylsulfonyloxy-4,4-dimethyl-tetrahydro-pyr-2-one
—— (S)-4-hexanolide 41035-07-8 C6H10O2
(S)-4-hexanolide
—— 6-(1,1-dimethylethoxy)-5-hydroxy-4,4-dimethyl-tetrahydro-pyr-2-one 118528-17-9 C11H20O4
6-(1,1-dimethylethoxy)-5-hydroxy-4,4-dimethyl-tetrahydro-pyr-2-one
—— 1,7,7-trimethyl-2,6-dioxabicyclo[2.2.2]octan-3,5-dione 859199-24-9 C9H12O4
1,7,7-trimethyl-2,6-dioxabicyclo[2.2.2]octan-3,5-dione
—— 3-Hydroxy-4-methyl-5-propan-2-yloxolan-2-one 160741-81-1 C8H14O3
3-Hydroxy-4-methyl-5-propan-2-yloxolan-2-one
—— (R)-2-<(E)-Bromomethylene>-5-hexanolide 126230-57-7 C7H9BrO2
(R)-2-<(E)-Bromomethylene>-5-hexanolide
—— Methyl (2S,3R)-(-)-tetrahydro-5-oxo-2-tridecyl-3-furancarboxylate 152785-62-1 C19H34O4
Methyl (2S,3R)-(-)-tetrahydro-5-oxo-2-tridecyl-3-furancarboxylate
—— (1S,5R,6S)-1,5,6-Trimethyl-5-[2-(2-methyl-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-1,2,3,4,5,6,7,8-octahydro-naphthalene-1-carboxylic acid methyl ester 125446-40-4 C23H36O4
(1S,5R,6S)-1,5,6-Trimethyl-5-[2-(2-methyl-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-1,2,3,4,5,6,7,8-octahydro-naphthalene-1-carboxylic acid methyl ester
—— 4,10,22-Trioxadodecacyclo[12.11.0.02,12.03,5.03,8.05,25.06,21.07,19.09,18.013,17.015,24.016,20]pentacos-16-ene-11,23-dione 120497-70-3 C22H16O5
4,10,22-Trioxadodecacyclo[12.11.0.02,12.03,5.03,8.05,25.06,21.07,19.09,18.013,17.015,24.016,20]pentacos-16-ene-11,23-dione
—— <3aR-(3aα,4α,5β,6aα)>-Hexahydro-4-(hydroxymethyl)-5-hydroxy-1H-cyclopenta<c>furan-1-on 90900-53-1 C8H12O4
<3aR-(3aα,4α,5β,6aα)>-Hexahydro-4-(hydroxymethyl)-5-hydroxy-1H-cyclopenta<c>furan-1-on
—— (Z,4S,5S)-dihydro-4-hydroxy-5-methyl-3-tetradecylidenefuran-2(3H)-one —— C19H34O3
(Z,4S,5S)-dihydro-4-hydroxy-5-methyl-3-tetradecylidenefuran-2(3H)-one
—— (+/-)-epilitsenolide C2 79980-81-7 C19H34O3
(+/-)-epilitsenolide C2
—— (4R,5R)-4-Phenyl-5-(3-phenyl-propyl)-dihydro-furan-2-one 125159-61-7 C19H20O2
(4R,5R)-4-Phenyl-5-(3-phenyl-propyl)-dihydro-furan-2-one
—— 5,11-Dioxo-10-oxadecacyclo<11.9.0.0<sup>2,9</sup>.0<sup>3,7</sup>.0<sup>4,22</sup>.0<sup>6,18</sup>.0<sup>8,17</sup>.0<sup>12,16</sup>.0<sup>14,21</sup>.0<sup>15,19</sup>>docosan-1(22),17-dien-20-syn-carbonitril 120575-54-4 C22H15NO3
5,11-Dioxo-10-oxadecacyclo<11.9.0.0<sup>2,9</sup>.0<sup>3,7</sup>.0<sup>4,22</sup>.0<sup>6,18</sup>.0<sup>8,17</sup>.0<sup>12,16</sup>.0<sup>14,21</sup>.0<sup>15,19</sup>>docosan-1(22),17-dien-20-syn-carbonitril
—— Rjzvafmwwhxnjr-ywahftaisa- 84077-33-8 C18H26O6
Rjzvafmwwhxnjr-ywahftaisa-
—— Rjzvafmwwhxnjr-nwbjouoxsa- 84077-33-8 C18H26O6
Rjzvafmwwhxnjr-nwbjouoxsa-
—— 9,21-Dioxaundecacyclo<11,11.0.0<sup>2,11</sup>.0<sup>3,7</sup>.0<sup>4,24</sup>.0<sup>5,20</sup>.0<sup>6,18</sup>.0<sup>8,17</sup>.0<sup>12,16</sup>.0<sup>14,23</sup>.0<sup>15,19</sup>>tetracosa-3,15-dien-10,22-dion 120497-68-9 C22H16O4
9,21-Dioxaundecacyclo<11,11.0.0<sup>2,11</sup>.0<sup>3,7</sup>.0<sup>4,24</sup>.0<sup>5,20</sup>.0<sup>6,18</sup>.0<sup>8,17</sup>.0<sup>12,16</sup>.0<sup>14,23</sup>.0<sup>15,19</sup>>tetracosa-3,15-dien-10,22-dion