(-)-(1E,5R)-1-[4-(benzyloxy)phenyl]-5-(tripropylsilyloxy)isos-1-en-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (-)-(1E,5R)-1-[4-(benzyloxy)phenyl]-5-(tripropylsilyloxy)isos-1-en-3-one
• 英文别名: (E,5R)-1-(4-phenylmethoxyphenyl)-5-tripropylsilyloxyicos-1-en-3-one
• 化学式: C₄₂H₆₈O₃Si
• 分子量: 649.086
• InChiKey: SRVQKFHNIZWOMZ-VGHRPJPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.28
• 重原子数：
  46
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (-)-(1E,5R)-1-[4-(benzyloxy)phenyl]-5-(tripropylsilyloxy)isos-1-en-3-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以67%的产率得到(-)-(R)-1-(4-hydroxyphenyl)-5-(tripropylsilyloxy)isocan-3-one
  参考文献：
  名称：

  Forming Spirocyclohexadienone-Oxocarbenium Cation Species in the Biomimetic Synthesis of Amomols

  摘要：

  The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized for the first time and were biologically evaluated on Plasmodium falciparum.

  DOI：

  10.1021/jo102414s
• 作为产物：
  描述：

  十六醛 在 咪唑 、 四氧化锇 、 正丁基锂 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 (-)-(1E,5R)-1-[4-(benzyloxy)phenyl]-5-(tripropylsilyloxy)isos-1-en-3-one
  参考文献：
  名称：

  Forming Spirocyclohexadienone-Oxocarbenium Cation Species in the Biomimetic Synthesis of Amomols

  摘要：

  The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized for the first time and were biologically evaluated on Plasmodium falciparum.

  DOI：

  10.1021/jo102414s

文献信息

• Forming Spirocyclohexadienone-Oxocarbenium Cation Species in the Biomimetic Synthesis of Amomols
  作者：Mariam Traoré、Marjorie Maynadier、Florence Souard、Luc Choisnard、Henri Vial、Yung-Sing Wong

  DOI：10.1021/jo102414s

  日期：2011.3.4

  The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized for the first time and were biologically evaluated on Plasmodium falciparum.