[(2R)-3-[2-chloroethoxy(methoxy)phosphoryl]oxy-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxypropyl] hexadecanoate | 878754-21-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2R)-3-[2-chloroethoxy(methoxy)phosphoryl]oxy-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxypropyl] hexadecanoate
• CAS: 878754-21-3
• 化学式: C₄₂H₇₆ClO₁₁P
• 分子量: 823.486
• InChiKey: NVMCPDHRPDSJQH-QYFPJXSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  55
• 可旋转键数：
  38
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R)-3-[2-chloroethoxy(methoxy)phosphoryl]oxy-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxypropyl] hexadecanoate 、 三甲胺 以 乙醇 、 氯仿 为溶剂， 反应 60.0h， 以65%的产率得到[(2R)-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxy-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

  摘要：

  The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F-2t-isoprostane and ent-15-epi-F-2t-isoprostane has allowed for the selective preparation of 15-F-2t-isoprostanyl phosphatidylethanolamine and ent-15-epi-F-2t-isoprostanyl phosphatidylcholine. The nature of the head-groups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary H-1 NMR and P-31 NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.

  DOI：

  10.1021/jo0518553
• 作为产物：
  描述：

  2-O-(benzyloxymethyl)-1-O-palmitoyl-sn-glycerol 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 39.0h， 生成 [(2R)-3-[2-chloroethoxy(methoxy)phosphoryl]oxy-2-[(Z)-7-[(1R,2S,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoyl]oxypropyl] hexadecanoate
  参考文献：
  名称：

  Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine

  摘要：

  The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F-2t-isoprostane and ent-15-epi-F-2t-isoprostane has allowed for the selective preparation of 15-F-2t-isoprostanyl phosphatidylethanolamine and ent-15-epi-F-2t-isoprostanyl phosphatidylcholine. The nature of the head-groups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary H-1 NMR and P-31 NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.

  DOI：

  10.1021/jo0518553