1,2-bis[(E,E)-2,4-tetradecadienoyl]-3-(4-methoxybenzyl)-sn-glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-bis[(E,E)-2,4-tetradecadienoyl]-3-(4-methoxybenzyl)-sn-glycerol
• 英文别名: [(2S)-3-[(4-methoxyphenyl)methoxy]-2-[(2E,4E)-tetradeca-2,4-dienoyl]oxypropyl] (2E,4E)-tetradeca-2,4-dienoate
• 化学式: C₃₉H₆₀O₆
• 分子量: 624.902
• InChiKey: LQENZSKYYRHVPY-CGOBQBQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  45
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis[(E,E)-2,4-tetradecadienoyl]-3-(4-methoxybenzyl)-sn-glycerol 在 二甲基溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以80%的产率得到1,2-bis[(E,E)-2,4-tetradecadienoyl]-sn-glycerol
  参考文献：
  名称：

  Syntheses of Polymerizable Monoacylglycerols and 1,2-Diacyl-sn-glycerols

  摘要：

  The first chemical syntheses of polymerizable monoacylglycerol and 1,2-diacyl-sn-glycerol are reported. The monodienoylglycerol is obtained in 80% yield from 1,2-O-isopropylidene-sn-glycerol and dienoyl fatty acid. The dienoic acid is accessible in 60% yield from the base-catalyzed hydrolysis of dienoyl ester, which is synthesized from the Wittig-Horner reaction of aldehyde and trimethyl 4-phosphonocrotonate. The acylation is carried out in the presence of 4-(dimethylamino)pyridine and dicyclohexylcarbodiimide. The use of excess protected glycerol relative to fatty acid affords the acylated product in high yield. The final step is the deprotection of isopropylidene group using dilute HCl solution. The 1,2-diacyl-sn-glycerol is synthesized by acylation of 3-(4-methoxybenzyl)-sn-glycerol with dienoyl fatty acid in the presence of 4-(dimethylamino)pyridine and dicyclohexylcarbodiimide. The removal of the 4-methoxybenzyl group by dimethylboron bromide catalyzed hydrolysis is especially useful in the synthesis of polymerizable lipids because the deprotection proceeds without any apparent effect on the dienoyl polymerizable group and without detectable isomerization of 1,2-diacylglycerol to 1,3-diacylglycerol. The overall yield for the synthesis of the polymerizable 1,2-diacyl-sn-glycerol from the dienoyl fatty acid is ca. 50%.

  DOI：

  10.1021/jo960010b
• 作为产物：
  描述：

  (S)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 1,2-bis[(E,E)-2,4-tetradecadienoyl]-3-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  Syntheses of Polymerizable Monoacylglycerols and 1,2-Diacyl-sn-glycerols

  摘要：

  The first chemical syntheses of polymerizable monoacylglycerol and 1,2-diacyl-sn-glycerol are reported. The monodienoylglycerol is obtained in 80% yield from 1,2-O-isopropylidene-sn-glycerol and dienoyl fatty acid. The dienoic acid is accessible in 60% yield from the base-catalyzed hydrolysis of dienoyl ester, which is synthesized from the Wittig-Horner reaction of aldehyde and trimethyl 4-phosphonocrotonate. The acylation is carried out in the presence of 4-(dimethylamino)pyridine and dicyclohexylcarbodiimide. The use of excess protected glycerol relative to fatty acid affords the acylated product in high yield. The final step is the deprotection of isopropylidene group using dilute HCl solution. The 1,2-diacyl-sn-glycerol is synthesized by acylation of 3-(4-methoxybenzyl)-sn-glycerol with dienoyl fatty acid in the presence of 4-(dimethylamino)pyridine and dicyclohexylcarbodiimide. The removal of the 4-methoxybenzyl group by dimethylboron bromide catalyzed hydrolysis is especially useful in the synthesis of polymerizable lipids because the deprotection proceeds without any apparent effect on the dienoyl polymerizable group and without detectable isomerization of 1,2-diacylglycerol to 1,3-diacylglycerol. The overall yield for the synthesis of the polymerizable 1,2-diacyl-sn-glycerol from the dienoyl fatty acid is ca. 50%.

  DOI：

  10.1021/jo960010b