methyl (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate | 96244-10-9

• 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: methyl (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
• CAS: 96244-10-9
• 化学式: C₂₁H₃₆O₅
• 分子量: 368.514
• InChiKey: PJDMFGSFLLCCAO-UOPBBOGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate 在 porcine liver esterase 、 Li⁽¹⁺⁾*H⁽¹⁸⁾O^(1-) 、 重氧水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (1,1-(18)O2)-8-epi-prostaglandin F2α
  参考文献：
  名称：

  Enzymatic synthesis of dioxygen-18 labelled 8-epi-prostanglandin F2α and its use in quantitative GC-tandem MS

  摘要：

  DOI：

  10.1002/(sici)1099-1344(199706)39:6<531::aid-jlcr3>3.0.co;2-o
• 作为产物：
  描述：

  methyl (Z)-7-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-formylcyclopentyl]hept-5-enoate 在 (-)-(S)-BINAL-H 、 四丁基氟化铵 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 methyl (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
  参考文献：
  名称：

  Hwang, Seong Woo; Adiyaman, Mustafa; Khanapure, Subhash, Journal of the American Chemical Society, 1994, vol. 116, # 23, p. 10829 - 10830

  摘要：

  DOI：

文献信息

• Stereocontrolled Access to Isoprostanes via a Bicyclo[3.3.0]octene Framework
  作者：Camille Oger、Yasmin Brinkmann、Samira Bouazzaoui、Thierry Durand、Jean-Marie Galano

  DOI：10.1021/ol802104z

  日期：2008.11.6

  stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo[3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework.

  我们报告了基于双环α，β-环氧酮中间体6的异丙醇全合成的简单且高度立体控制的策略。双环[3.3.0]辛烯骨架允许试剂的立体定向，从而允许立体选择性环氧化，非对映选择性酮还原和区域选择性环氧化物否则无法通过简单的环戊烯框架打开。
• Total Synthesis of (15<i>R</i>)- and (15<i>S</i>)-F_2t-Isoprostanes by a Biomimetic Process Using the Cyclization of Acyclic Dihydroxylated Octa-5,7-dienyl Radicals
  作者：Thierry Durand、Alexandre Guy、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1021/jo0109624

  日期：2002.5.1

  We report a new route to F-2t-IsoP (formerly named 8-epi-PGF(2alpha)) using a biomimetic radical cyclization of a highly functionalized C20 precursor. The strategy employed gives a beta-hydroxy free radical followed by molecular oxygen trapping, which is an unusual method for quenching carbon free radicals. We observed the formation of unique diastereoisomers (15R)- and (15S)-F-2t-IsoP. This result is consistent with a strong stereoelectronic control associated with a steric effect initiated by the side chains alpha and omega on the cyclopentane ring.