(+/-)-4-(tert-butyldimethylsilyloxy)-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-one | 872428-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-4-(tert-butyldimethylsilyloxy)-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-one
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxy-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-one；4-[tert-butyl(dimethyl)silyl]oxy-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-one
• CAS: 872428-15-4
• 化学式: C₂₃H₃₆O₃Si
• 分子量: 388.623
• InChiKey: HANMSNLJGTXFAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(tert-butyldimethylsilyloxy)-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以76%的产率得到(+/-)-1-cyclohexylidene-4-hydroxy-4-(4-methoxyphenyl)butan-2-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
• 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 (+/-)-4-(tert-butyldimethylsilyloxy)-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-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