[(3aR,4R,5R,6aS)-4-(1-acetyloxy-5-phenylpent-2-ynyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate | 1251949-15-1

• 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: [(3aR,4R,5R,6aS)-4-(1-acetyloxy-5-phenylpent-2-ynyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate
• CAS: 1251949-15-1
• 化学式: C₃₃H₃₀O₆
• 分子量: 522.598
• InChiKey: KQXGHMVPBCKURQ-QTXDFFDPSA-N

物化性质

• 沸点：
  710.9±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,5R,6aS)-4-(1-acetyloxy-5-phenylpent-2-ynyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) 、 叔丁醇 作用下， 以 水 、 丁酮 为溶剂， 反应 23.0h， 以90%的产率得到(3aR,4R,5R,6aS)-六氢-2-氧代-4-[(1E)-3-氧代-5-苯基-1-戊烯基]-2H-环戊并[b]呋喃-5-基 [1,1’-联苯]-4-甲酸酯
  参考文献：
  名称：

  The Meyer–Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

  摘要：

  Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.069
• 作为产物：
  描述：

  4-苯基-1-丁炔 、 乙酸酐 、 对苯基苯甲酰Corey醛 在 正丁基锂 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到[(3aR,4R,5R,6aS)-4-(1-acetyloxy-5-phenylpent-2-ynyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate
  参考文献：
  名称：

  The Meyer–Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

  摘要：

  Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.069

文献信息

• The Meyer–Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost
  作者：Giuseppe Zanoni、Alessandro D’Alfonso、Alessio Porta、Lazzaro Feliciani、Steven P. Nolan、Giovanni Vidari

  DOI：10.1016/j.tet.2010.07.069

  日期：2010.9

  Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.