| 137718-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 137718-38-8；137819-54-6
• 化学式: C₄₃H₅₆O₄SSi
• 分子量: 697.067
• InChiKey: PDVQQYRKFQDUNO-MHYZNKBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.72
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 氢氟酸 、 间氯过氧苯甲酸 、 三甲氧基磷 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 前列腺素E(2)甲酯
  参考文献：
  名称：

  Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester

  摘要：

  Intramolecular Rh(II) carboxylate catalyzed cyclization of an alpha-diazo beta-methylene ketone to form a fused cyclopropane is shown to compete efficiently with beta-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE2 methyl ester 1. Prostaglandins having the 8-beta configuration, recently identified as being physiologically important, can also be prepared using this approach.

  DOI：

  10.1021/jo00028a012
• 作为产物：
  描述：

  Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate 在 dirhodium tetraacetate 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester

  摘要：

  Intramolecular Rh(II) carboxylate catalyzed cyclization of an alpha-diazo beta-methylene ketone to form a fused cyclopropane is shown to compete efficiently with beta-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE2 methyl ester 1. Prostaglandins having the 8-beta configuration, recently identified as being physiologically important, can also be prepared using this approach.

  DOI：

  10.1021/jo00028a012