2,2-dimethyl-4-trimethylsilyloxy-5-phenyl-1,3-dioxola-4-ene | 111718-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-4-trimethylsilyloxy-5-phenyl-1,3-dioxola-4-ene
• 英文别名: (2,2-Dimethyl-5-phenyl-1,3-dioxol-4-yl)oxy-trimethylsilane
• CAS: 111718-69-5
• 化学式: C₁₄H₂₀O₃Si
• 分子量: 264.397
• InChiKey: LVNRPATURXKAQA-UHFFFAOYSA-N

物化性质

• 沸点：
  278.3±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-4-trimethylsilyloxy-5-phenyl-1,3-dioxola-4-ene 在 Merrifield resin - (D)-mandelic acid 作用下， 生成 (S)-(+)-扁桃酸 、 D-扁桃酸
  参考文献：
  名称：

  A first approach to asymmetric protonation via a polymer supported chiral proton donor

  摘要：

  Asymmetric protonation of achiral silyl enol ethers employing chiral proton donors is described for the first time. We have obtained modest enantiomeric excesses by carrying out these reactions in homogeneous solution. The subject of this paper is to report in a preliminary fashion the substantially improved asymmetric induction that can be achieved by supporting the proton donor on a polymeric resin (up to 94% ee). A temperature effect is observed and discussed.

  DOI：

  10.1016/s0040-4039(00)76652-4
• 作为产物：
  描述：

  三甲基氯硅烷 、 2,2-二甲基-5-苯基-1,3-二氧杂烷-4-酮 在 lithium diisopropyl amide 作用下， 生成 2,2-dimethyl-4-trimethylsilyloxy-5-phenyl-1,3-dioxola-4-ene
  参考文献：
  名称：

  Gerlach, Uwe; Huenig, Siegfried, Angewandte Chemie, 1987, vol. 99, # 12, p. 1323 - 1325

  摘要：

  DOI：

文献信息

• Deracemization of silyl enol ethers
  作者：Florine Cavelier、Sylvie Gomez、Robert Jacquier、Jean Verducci

  DOI：10.1016/s0957-4166(00)82229-6

  日期：1993.1

  The deracemization by enantioselective protonation of silyl enol ethers was tested using 2,2-dimethyl 5-phenyl 1,3-dioxolan 4-one 1. The results obtained, especially with pantolactone as a chiral proton donor, are better than when the deracemization is carried out with the lithium enolate of 1.
• Gerlach, Uwe; Huenig, Siegfried, Angewandte Chemie, 1987, vol. 99, # 12, p. 1323 - 1325
  作者：Gerlach, Uwe、Huenig, Siegfried

  DOI：——

  日期：——
• A first approach to asymmetric protonation via a polymer supported chiral proton donor
  作者：Florine Cavelier、Sylvie Gomez、Robert Jacquier、Jean Verducci

  DOI：10.1016/s0040-4039(00)76652-4

  日期：1994.5

  Asymmetric protonation of achiral silyl enol ethers employing chiral proton donors is described for the first time. We have obtained modest enantiomeric excesses by carrying out these reactions in homogeneous solution. The subject of this paper is to report in a preliminary fashion the substantially improved asymmetric induction that can be achieved by supporting the proton donor on a polymeric resin (up to 94% ee). A temperature effect is observed and discussed.