5-epi-F_2t-isoprostane | 249934-93-8

• 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: 5-epi-F_2t-isoprostane
• 英文别名: 5-epi-5-F2t-IsoP；(E,5R)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(Z)-oct-2-enyl]cyclopentyl]-5-hydroxyhept-6-enoic acid
• CAS: 249934-93-8
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: RZCPXIZGLPAGEV-NVWAOVOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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

• 作为反应物：
  描述：

  重氮甲烷 、 5-epi-F_2t-isoprostane 生成 (E)-(R)-7-[(1S,2R,3R,5S)-3,5-Dihydroxy-2-((Z)-oct-2-enyl)-cyclopentyl]-5-hydroxy-hept-6-enoic acid methyl ester
  参考文献：
  名称：

  Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane

  摘要：

  The total synthesis of the 5-F-2t-isoprostane I and its 5-epimer 2 from diacetone-D-glucose is described. We report preliminary data on the vascular properties of these compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00473-5
• 作为产物：
  描述：

  ethyl (E)-7-[(1S,2R,3R,5S)-3-acetyloxy-5-hydroxy-2-[(Z)-oct-2-enyl]cyclopentyl]-5-oxohept-6-enoate 在 lithium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-epi-F_2t-isoprostane
  参考文献：
  名称：

  5-F_2t-Isoprostane, A Human Hormone?

  摘要：

  DOI：

  10.1021/ja990859k

文献信息

• A Cross-Metathesis Route to the 5-F₂-Isoprostanes
  作者：Bhaumik A. Pandya、Marc L. Snapper

  DOI：10.1021/jo702702s

  日期：2008.5.1

  A library of eight 5-F-2-isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and alpha,beta-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F-2 isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.
• 5-F_2t-Isoprostane, A Human Hormone?
  作者：Douglass F. Taber、Kazuo Kanai、Richard Pina

  DOI：10.1021/ja990859k

  日期：1999.9.1
• Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane
  作者：Thierry Durand、Jean-Luc Cracowski、Alexandre Guy、Jean-Claude Rossi

  DOI：10.1016/s0960-894x(01)00473-5

  日期：2001.9

  The total synthesis of the 5-F-2t-isoprostane I and its 5-epimer 2 from diacetone-D-glucose is described. We report preliminary data on the vascular properties of these compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.