ethyl (E)-3-(tert-butyldimethylsilyloxy)-3-methyl-5-phenylpent-4-enoate | 1207866-21-4

• 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: ethyl (E)-3-(tert-butyldimethylsilyloxy)-3-methyl-5-phenylpent-4-enoate
• 英文别名: ethyl (E)-3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-5-phenylpent-4-enoate
• CAS: 1207866-21-4
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: OEDQRXDLCLHAKT-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 、 苄叉丙酮 在 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane 、 盐酸 、 水 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.0h， 以51%的产率得到5-氧代-3-苯基己酸乙酯
  参考文献：
  名称：

  Highly Effective Vinylogous Mukaiyama−Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane

  摘要：

  Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) performed as an excellent acid catalyst for the vinylogous Mukaiyama-Michael reaction of alpha,beta-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol %). This carbon acid-mediated VMM reaction provides a powerful synthetic methodology to construct highly substituted gamma-butenolide structure.

  DOI：

  10.1021/jo902641g

文献信息

• Highly Effective Vinylogous Mukaiyama−Michael Reaction Catalyzed by Silyl Methide Species Generated from 1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane
  作者：Arata Takahashi、Hikaru Yanai、Min Zhang、Takaaki Sonoda、Masaaki Mishima、Takeo Taguchi

  DOI：10.1021/jo902641g

  日期：2010.2.19

  Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) performed as an excellent acid catalyst for the vinylogous Mukaiyama-Michael reaction of alpha,beta-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf2CHCH2CHTf2 to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol %). This carbon acid-mediated VMM reaction provides a powerful synthetic methodology to construct highly substituted gamma-butenolide structure.