(E,E)-1-(trimethylsilylmethyl)-2-methyl-4-phenyl-1,3-butadiene

• 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: (E,E)-1-(trimethylsilylmethyl)-2-methyl-4-phenyl-1,3-butadiene
• 化学式: C₁₅H₂₂Si
• 分子量: 230.425
• InChiKey: ARYYWXOYXZCSBK-CYZWUHAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  (2-trimethylsilylethylidene)triphenylphosphorane 、 苄叉丙酮 以 四氢呋喃 为溶剂， 生成 (1Z,3E)-1-(trimethylsilylmethyl)-2-methyl-4-phenyl-1,3-butadiene 、 (E,E)-1-(trimethylsilylmethyl)-2-methyl-4-phenyl-1,3-butadiene
  参考文献：
  名称：

  The Stereoselective Synthesis of Conjugated Allylsilanes

  摘要：

  2-trimethylsilylethylidenetriphenylphosphorane (5) (Seyferth-Wittig reagent) reacts stereoselectively with the carbonyl compounds 6a-f to give the conjugated allylsilanes 7a-f, each as a mixture of E- and Z-isomers. The stereoselectivity of reactions of E-cinnamaldehyde (6c) with 5 has been investigated at different temperatures. A successful E-stereoselective synthesis of 7c was achieved by reacting 5 with E-cinnamaldehyde (6c) under the conditions of a Wittig-Schlosser modification reaction. Structures of the allylsilanes 7a-f were deduced by compatible analytical and spectroscopic (IR, (HNMR)-H-1, C-13 NMR, and GC/MS) measurements. An assignment of the E:Z ratios of 7a-f is based on their H-1 NMR spectral data.

  DOI：

  10.1080/10426500600616589

文献信息

• The Stereoselective Synthesis of Conjugated Allylsilanes
  作者：Mohamed Refat H. Mahran、Hisham Abdallah A. Yosef、Franz Effenberger

  DOI：10.1080/10426500600616589

  日期：2006.10.1

  2-trimethylsilylethylidenetriphenylphosphorane (5) (Seyferth-Wittig reagent) reacts stereoselectively with the carbonyl compounds 6a-f to give the conjugated allylsilanes 7a-f, each as a mixture of E- and Z-isomers. The stereoselectivity of reactions of E-cinnamaldehyde (6c) with 5 has been investigated at different temperatures. A successful E-stereoselective synthesis of 7c was achieved by reacting 5 with E-cinnamaldehyde (6c) under the conditions of a Wittig-Schlosser modification reaction. Structures of the allylsilanes 7a-f were deduced by compatible analytical and spectroscopic (IR, (HNMR)-H-1, C-13 NMR, and GC/MS) measurements. An assignment of the E:Z ratios of 7a-f is based on their H-1 NMR spectral data.