ent-15-epi-F_2c-isoprostane

• 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: ent-15-epi-F_2c-isoprostane
• 英文别名: ent-15-epi-15-F2c-IsoP；(Z)-7-[(1S,2R,3S,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: PXGPLTODNUVGFL-DCCGFWISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-辛烯-3-醇 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 9-borabicyclo[3.3.1]nonane dimer 、 四丁基氟化铵 、 四丁基氯化铵 、 碘 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 52.2h， 生成 ent-15-epi-F_2c-isoprostane
  参考文献：
  名称：

  Stereodivergent Synthesis of All 15-F₂ Isoprostanes

  摘要：

  Isoprostanes, lipid metabolites generated from free radical oxidation of membrane-bound arachidonic acid, have been detected in organisms subjected to oxidative stress; however, the function and cellular targets of the isoprostanes are unclear. As an initial step toward studying the biological role of these molecules, we report the preparation of all known and anticipated 15-F2 isoprostanes. The stereodivergent strategy to the complete isoprostane library features a ring-opening metathesis to introduce the cis-alkyl side chains that are characteristic of this class of molecules. Resolution to the individual stereoisomers can be accomplished by either a catalytic asymmetric reduction or an auxiliary-based separation protocol. In either case, the individual isomers can be converted to the corresponding 15-F2 isoprostanes through a straightforward functionalization of the carboxylic acid-containing side chain. The availability of this complete 15-F2 isoprostane library, containing both known and anticipated lipid metabolites, allows for the first time the side-by-side evaluation of these compounds in a variety of biological assays.

  DOI：

  10.1021/ja027154u

文献信息

• Stereodivergent Synthesis of All 15-F₂ Isoprostanes
  作者：Thomas O. Schrader、Marc L. Snapper

  DOI：10.1021/ja027154u

  日期：2002.9.1

  Isoprostanes, lipid metabolites generated from free radical oxidation of membrane-bound arachidonic acid, have been detected in organisms subjected to oxidative stress; however, the function and cellular targets of the isoprostanes are unclear. As an initial step toward studying the biological role of these molecules, we report the preparation of all known and anticipated 15-F2 isoprostanes. The stereodivergent strategy to the complete isoprostane library features a ring-opening metathesis to introduce the cis-alkyl side chains that are characteristic of this class of molecules. Resolution to the individual stereoisomers can be accomplished by either a catalytic asymmetric reduction or an auxiliary-based separation protocol. In either case, the individual isomers can be converted to the corresponding 15-F2 isoprostanes through a straightforward functionalization of the carboxylic acid-containing side chain. The availability of this complete 15-F2 isoprostane library, containing both known and anticipated lipid metabolites, allows for the first time the side-by-side evaluation of these compounds in a variety of biological assays.