rac-1-O-cis-9-octadecenyl-2-O-<(methoxyethoxy)methyl>glycerol | 93135-81-0

• 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: rac-1-O-cis-9-octadecenyl-2-O-<(methoxyethoxy)methyl>glycerol
• 英文别名: rac-1-O-cis-9-octadecenyl-2-O-[(methoxyethoxy)methyl]glycerol
• CAS: 93135-81-0
• 化学式: C₂₅H₅₀O₅
• 分子量: 430.669
• InChiKey: AFTLZPGTWMPUJN-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  30.0
• 可旋转键数：
  25.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  rac-1-O-cis-9-octadecenyl-2-O-<(methoxyethoxy)methyl>glycerol 在 吡啶 、 三乙胺 、 zinc dibromide 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 29.5h， 生成 [2-hydroxy-3-[(Z)-octadec-9-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain

  摘要：

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

  DOI：

  10.1021/jm00379a015
• 作为产物：
  描述：

  2-O-<(methoxyethoxy)methyl>-1,3-benzylideneglycerol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 16.0h， 生成 rac-1-O-cis-9-octadecenyl-2-O-<(methoxyethoxy)methyl>glycerol
  参考文献：
  名称：

  Facile synthesis of platelet-activating factor and racemic analogs containing unsaturation in the sn-1-alkyl chain

  摘要：

  Platelet-activating factor, 1 (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position (2, 4, 5) were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated either phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.

  DOI：

  10.1021/jm00379a015