(E,2R)-4-[tert-butyl(dimethyl)silyl]oxy-1,1,1-trifluoro-4-phenylbut-3-en-2-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E,2R)-4-[tert-butyl(dimethyl)silyl]oxy-1,1,1-trifluoro-4-phenylbut-3-en-2-ol
• 化学式: C₁₆H₂₃F₃O₂Si
• 分子量: 332.438
• InChiKey: VTPPCTNWQGHKGA-YPDDLIOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,2-三氟乙醛 、 tert-butyldimethyl(1-phenylvinyloxy)silane 在 (R)-binaphthol-derived titanium complex 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以14%的产率得到(R)-(+)-(2-hydroxy-3,3,3-trifluoropropyl)phenyl ketone
  参考文献：
  名称：

  Asymmetric Catalytic Friedel−Crafts Reaction of Silyl Enol Ethers with Fluoral:  A Possible Mechanism of the Mukaiyama-Aldol Reactions

  摘要：

  [GRAPHICS]The catalytic asymmetric Friedel-Crafts reaction of silyl enol ethers with fluoral proceeds under Mukaiyama-aldol conditions to give silyl enol ether products. The sequential diastereoselective reactions of the resultant silyl enol ethers with electrophiles provide highly enantiopure functionalized organofluorine compounds of material and pharmaceutical interest.

  DOI：

  10.1021/ol990330s

文献信息

• Asymmetric Catalytic Friedel−Crafts Reaction of Silyl Enol Ethers with Fluoral:  A Possible Mechanism of the Mukaiyama-Aldol Reactions
  作者：Akihiro Ishii、Jun Kojima、Koichi Mikami

  DOI：10.1021/ol990330s

  日期：1999.12.1

  [GRAPHICS]The catalytic asymmetric Friedel-Crafts reaction of silyl enol ethers with fluoral proceeds under Mukaiyama-aldol conditions to give silyl enol ether products. The sequential diastereoselective reactions of the resultant silyl enol ethers with electrophiles provide highly enantiopure functionalized organofluorine compounds of material and pharmaceutical interest.