1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine
• 英文别名: [(2S)-3-hexadecanoyloxy-2-(9-oxononanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• 化学式: C₃₃H₆₄NO₉P
• 分子量: 649.846
• InChiKey: PPTNNIINSOQWCE-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  44
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  9-氧代壬酸甲酯 在 硝酸铵 、 4-二甲氨基吡啶 、 sodium hydroxide 、 amberlyst-15 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 93.5h， 生成 1-palmitoyl-2-(9-oxo-nonanoyl)-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  新型生物活性磷脂：2-溶血磷脂酰胆碱（1）的花生四烯酸和亚油酸酯氧化产物的实用全合成。

  摘要：

  完成了九种新型磷脂的总合成，以简化对低密度脂蛋白中两种最丰富的多不饱和磷脂的2-溶血磷脂酰胆碱的花生四烯酸酯和亚油酸酯的氧化裂解后生成的化合物的鉴定和生物学测试。利用2-硫代呋喃作为4-氧代-2-丁烯酰基碳负离子等效物的有效通用合成提供了含有γ-酮-α，β-不饱和羰基官能团的磷脂。通过利用容易的顺式-反式异构化，可以将两种市售的顺式烯烃（2Z）-2-丁烯-1,4-二醇和2,5-二氢呋喃用作制备霍纳-沃兹沃思-埃蒙斯试剂4的原料。 -（二乙氧基磷酰基）-2E-丁烯醛，是合成2,4-二烯醛的重要组成部分。

  DOI：

  10.1021/jo0105383

文献信息

• Total Synthesis of γ-Hydroxy-α,β-Unsaturated Aldehydic Esters of Cholesterol and 2-Lysophosphatidylcholine
  作者：Yijun Deng、Robert G. Salomon

  DOI：10.1021/jo980861e

  日期：1998.10.1

  Free radical-induced oxidation of polyunsaturated fatty esters in low-density lipoproteins (LDLs) generates 2-lysophosphatidylcholine (PC) and cholesterol esters of gamma-hydroxy-alpha,beta-unsaturated aldehydic acids that covalently modify LDL protein, and protein adducts of the corresponding acids are found in human blood. The chemistry and structures of these compounds resemble those of (E)-4-hydroxy-2-nonenal (HNE), previously considered the most cytotoxic aldehyde released during peroxidation of linoleate and arachidonate esters. The present report details total syntheses of 2-lyse-PC and cholesteryl esters of (E)-9-hydroxy-12-oxododec-10-enoic and (E)-5-hydroxy-8-oxooct-6-enoic acid that presumably are derived in vivo from linoleate and arachidonate esters, respectively. The syntheses depend on the use of a 3,3-dimethyl-2,4-dioxolanyl moiety as a latent aldehyde from which the chemically sensitive gamma-hydroxy-alpha,beta-unsaturated aldehyde array can be generated in the final step. For the cholesteryl esters, generation of the aldehyde group by oxidative cleavage of a vicinal diol could be accomplished in very good yields with periodate. However, for esters of 2-lyso-PC, the target aldehydes were not obtained upon treatment of vicinal diol precursors with periodate owing to a novel oxidative cleavage of the gamma-hydroxy-alpha,beta-unsaturated aldehydes by periodate. Fortunately, treatment of the vicinal diol precursors with Pb(OAc)(4) at -80 degrees C delivered good yields (82-85%) of the desired phospholipid aldehydes.
• Novel Bioactive Phospholipids:  Practical Total Syntheses of Products from the Oxidation of Arachidonic and Linoleic Esters of 2-Lysophosphatidylcholine¹
  作者：Mingjiang Sun、Yijun Deng、Eugenia Batyreva、Wei Sha、Robert G. Salomon

  DOI：10.1021/jo0105383

  日期：2002.5.1

  Total syntheses of nine novel phospholipids were accomplished to facilitate the identification and biological testing of compounds that are generated upon oxidative cleavage of arachidonate and linoleate esters of 2-lysophosphatidylcholine, the two most abundant polyunsaturated phospholipids in low-density lipoprotein. An efficient general synthesis exploiting 2-lithiofuran as a 4-oxo-2-butenoyl carbanion

  完成了九种新型磷脂的总合成，以简化对低密度脂蛋白中两种最丰富的多不饱和磷脂的2-溶血磷脂酰胆碱的花生四烯酸酯和亚油酸酯的氧化裂解后生成的化合物的鉴定和生物学测试。利用2-硫代呋喃作为4-氧代-2-丁烯酰基碳负离子等效物的有效通用合成提供了含有γ-酮-α，β-不饱和羰基官能团的磷脂。通过利用容易的顺式-反式异构化，可以将两种市售的顺式烯烃（2Z）-2-丁烯-1,4-二醇和2,5-二氢呋喃用作制备霍纳-沃兹沃思-埃蒙斯试剂4的原料。 -（二乙氧基磷酰基）-2E-丁烯醛，是合成2,4-二烯醛的重要组成部分。