前列腺素杂质 | 155551-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 前列腺素杂质
• 英文名称: (1R,5S,6R,7S)-7-hydroxy-6-hydroxymethyl-2-oxabicyclo<3.3.0>octan-3-one
• 英文别名: (3aS,4S,5S,6aR)-5-hydroxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 155551-84-1
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: VYTZWRCSPHQSFX-BNHYGAARSA-N

物化性质

• 沸点：
  406.6±25.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  前列腺素杂质 在 草酰氯 、 potassium tert-butylate 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 methyl (Z)-7-[(1S,2R,3S,5R)-5-hydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]-3-triethylsilyloxycyclopentyl]hept-5-enoate
  参考文献：
  名称：

  Roland, Arlene; Durand, Thierry; Rondott, Benoit, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 11, p. 1149 - 1154

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4S,5S,6aR)-4-Benzyloxymethyl-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到前列腺素杂质
  参考文献：
  名称：

  Roland, Arlene; Durand, Thierry; Rondott, Benoit, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 11, p. 1149 - 1154

  摘要：

  DOI：

文献信息

• A free radical route to syn lactones and other prostanoid intermediates in isoprostaglandin synthesis.
  作者：Benoît Rondot、Thierry Durand、Jean Pierre Girard、Jean Claude Rossi、Laurent Schio、Subhash P. Khanapure、Joshua Rokach

  DOI：10.1016/s0040-4039(00)61401-6

  日期：1993.12

  The hex-5-enyl radical cyclization methodology was applied to the formation of optical active prostanoid intermediates with readily available diacetone-D-glucose as starting material. This result should lead to isoprostaglandins, a novel class of arachidonic acid metabolites obtained by a non-cyclooxygenase mechanism involving free radical-catalysed peroxidation of arachidonic acid.

  将六-5-烯基自由基环化方法应用于以易得的双丙酮-D-葡萄糖为起始原料的旋光类前列腺素中间体的形成。该结果应导致异前列腺素，一种通过涉及自由基催化的花生四烯酸的过氧化的非环氧合酶机制获得的新型花生四烯酸代谢物。
• Stereoselective synthesis of an isoprostane synthon via 8,12-free-radical cyclization
  作者：Johann Mulzer、Michael Czybowski、Jan-W Bats

  DOI：10.1016/s0040-4039(01)00348-3

  日期：2001.4

  Aiming at a stereocontrolled biomimetic synthesis of isoprostanes a fully stereocontrolled 8,12-free radical cyclization has been achieved via intermediate 10 by annulating an endocyclic radical to a butenolide acceptor double bond. In this way ent-12-epi-PGF2α(ent-2) can be prepared.

  针对异前列腺素的立体控制仿生合成，已经通过中间体10通过使内环自由基与丁烯酸内酯双键环合实现了完全立体控制的8,12-自由基的环化。以这种方式ENT -12-外延-PGF 2α（ENT - 2）可以被制备。
• A new approach to the synthesis of polyunsaturated deuterated isoprostanes: Total synthesis of d4-5-epi-8,12-iso-iPF3α-VI and d4-8,12-iso-iPF3α-VI
  作者：Chih-Tsung Chang、Pranav Patel、Vivek Gore、Wen-Liang Song、John A. Lawson、William S. Powell、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1016/j.bmcl.2009.09.099

  日期：2009.12

  The total and stereospecific synthesis of d(4)-5-epi-8,12-iso-iPF(3 alpha)-VI 55 and d(4)-8,12-iso-iPF(3 alpha)-VI 64, EPA-derived all-syn-isoprostanes (iPs), has been accomplished. Because of issues related to volatility and yield with some of the primary deuterated synthons an improved synthesis is presented. These two deuterated analogs were used to discover and quantify the presence of the corresponding endogenous isoprostanes in human urine. These assays may serve as a valuable index of oxidative stress in population with omega-3 fatty acid enriched diets containing eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and may also be useful as an index of the severity of inflammatory diseases such as atherosclerosis and Alzheimer's disease. (C) 2009 Elsevier Ltd. All rights reserved.
• Eicosapentaenoic-acid-derived isoprostanes: Synthesis and discovery of two major isoprostanes
  作者：Chih-Tsung Chang、Pranav Patel、Namin Kang、John A. Lawson、Wen-Liang Song、William S. Powell、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1016/j.bmcl.2008.09.008

  日期：2008.10

  The stereospecific synthesis of two all-syn-EPA-derived isoprostanes (iPs), 5-epi-8,12-iso-iPF(3 alpha)-VI 17 and 8,12-iso-iPF(3 alpha)-VI 18, has been accomplished. These two synthetic probes have been used to discover and identify their presence in human urine. The eventual quantitative measurement of these two iPs may be a valuable index of oxidative stress in people with eicosapentaenoic acid-(EPA) and docosahexaenoic acid-(DHA) enriched phospholipids. (c) 2008 Elsevier Ltd. All rights reserved.
• THEIL, FRITZ;SCHICK, HANS;NEDKOV, PETER;BOHME, MONIKA;HAFNER, BARBARA;SCH+, J. PRAKT. CHEM., 330,(1988) N, C. 893-899
  作者：THEIL, FRITZ、SCHICK, HANS、NEDKOV, PETER、BOHME, MONIKA、HAFNER, BARBARA、SCH+

  DOI：——

  日期：——