(1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one | 618387-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one
• 英文别名: benzoic acid 2-oxo-4-vinylhexahydrocyclopenta[b]furan-5-yl ester；[(3aR,4R,5R,6aS)-4-ethenyl-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• CAS: 618387-07-8
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: LUDQWRAFJJPGSN-SYQHCUMBSA-N

物化性质

• 熔点：
  69.6 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  430.0±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (3aR,4R,5R,6aS)-5-Hydroxy-4-vinyl-hexahydro-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2

  摘要：

  We describe the effect of allylic (C15) and homoallylic (C11) substituents on cross metathesis reactions with Corey lactone derivatives. This strategy has led to the successful syntheses of PGF(2 alpha) and PGJ(2). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.140
• 作为产物：
  描述：

  科里内酯 在 potassium tert-butylate 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S,5R,6R,7R)-7-(benzoyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2

  摘要：

  We describe the effect of allylic (C15) and homoallylic (C11) substituents on cross metathesis reactions with Corey lactone derivatives. This strategy has led to the successful syntheses of PGF(2 alpha) and PGJ(2). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.140

文献信息

• Enantio- and Stereospecific Syntheses of 15(<i>R</i>)-Me-PGD₂, A Potent and Selective DP₂−Receptor Agonist
  作者：Pranav Patel、Gue-Jae Lee、Seongjin Kim、Gail E. Grant、William S. Powell、Joshua Rokach

  DOI：10.1021/jo801190m

  日期：2008.9.19

  The first total synthesis of 15(R)-Me-PGD2 3 is reported. The synthesis is based on the enantioselective and stereospecific syntheses of synthon 17 and its attachment to the five-membered ring by a olefin cross metathesis reaction. This approach permits the introduction of a side chain with a predetermined stereogenic center into the prostanoid ring, resulting in the synthesis of 15R-methyl prostaglandin

  报道了15（R）-Me-PGD2 3的第一个全合成。该合成是基于合成子17的对映选择性和立体特异性合成及其通过烯烃交叉复分解反应与五元环的连接。该方法允许将具有预定立体异构中心的侧链引入前列腺素环，从而合成15R-甲基前列腺素D2，并允许快速接近其他前列腺素。
• A short multigram asymmetric synthesis of prostanoid scaffolds
  作者：Dominique Depré、Lian-Yong Chen、Léon Ghosez

  DOI：10.1016/s0040-4020(03)00920-7

  日期：2003.8

  Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from gamma-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantionneric purities. (C) 2003 Elsevier Ltd. All rights reserved.