(+/-)-(E)-1-(tert-butyldimethylsilyloxy)-1-(4-methoxyphenyl)pentadec-4-en-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-(E)-1-(tert-butyldimethylsilyloxy)-1-(4-methoxyphenyl)pentadec-4-en-3-one
• 英文别名: (E)-1-[tert-butyl(dimethyl)silyl]oxy-1-(4-methoxyphenyl)pentadec-4-en-3-one
• 化学式: C₂₈H₄₈O₃Si
• 分子量: 460.773
• InChiKey: DSHMLEFCAMQOQE-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one 在 Hoveyda-Grubbs catalyst second generation N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-(E)-1-(tert-butyldimethylsilyloxy)-1-(4-methoxyphenyl)pentadec-4-en-3-one
  参考文献：
  名称：

  Elongation of β-hydroxyenones by cross-metathesis

  摘要：

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.037

文献信息

• Elongation of β-hydroxyenones by cross-metathesis
  作者：Franck A. Silva、Véronique Gouverneur

  DOI：10.1016/j.tetlet.2005.10.037

  日期：2005.12

  Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retroaldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and penterione using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metatbesis reactions, silyl-protected beta-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. (c) 2005 Elsevier Ltd. All rights reserved.