(+/-)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy][3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-cyclopentenone | 1019857-17-0

• 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: (+/-)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy][3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-cyclopentenone
• CAS: 1019857-17-0
• 化学式: C₂₅H₄₂O₄Si₂
• 分子量: 462.777
• InChiKey: IBRDOOBSKYVGQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.29
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy][3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-cyclopentenone 、 乙烯基溴化镁 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以59%的产率得到(2RS,4SR)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy][3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone
  参考文献：
  名称：

  Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms

  摘要：

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.

  DOI：

  10.1021/jo702635t
• 作为产物：
  描述：

  (+/-)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-cyclopentenone 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以78%的产率得到(+/-)-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy][3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-cyclopentenone
  参考文献：
  名称：

  Synthesis of the Potent Anticancer Agents Ottelione A and Ottelione B in Both Racemic and Natural Optically Pure Forms

  摘要：

  The powerful antitumor agents ottelione A and B were synthesized in racemic form by a method that relies on selective ring closing metathesis. Optically pure natural (+)-ottelione A was then made from D-ribose, via an alpha-keto cyclopropane. A key feature of the route is that the cyclopropyl group controls the stereochemistry in the attachment of the ArCH2 unit and is then converted by the action of SmI2 into a vinyl group, so that the substituents on the resulting five-membered ring have the required trans relationship. Epimerization of an intermediate gave access, by the same method to the trans ring fused isomer (-)-ottelione B.

  DOI：

  10.1021/jo702635t