(E)-2-methyl-6-phenyl-5-hexene-1,2-diol | 199458-76-9

• 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)-2-methyl-6-phenyl-5-hexene-1,2-diol
• 英文别名: (E)-2-methyl-6-phenylhex-5-ene-1,2-diol
• CAS: 199458-76-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: ZFSHXMPHRJNVIE-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-6-phenyl-5-hexene-1,2-diol 在 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 tert-Butyl-dimethyl-((1R,3S,4R,7R)-1-methyl-3-phenyl-2-oxa-bicyclo[2.2.1]hept-7-yloxy)-silane
  参考文献：
  名称：

  An Intramolecular Prins Double Cyclization Catalyzed by Silyl Triflates¹

  摘要：

  Several intramolecular Prins double cyclizations are reported. The 2-alkyl 5-hepten-1,2-diols and their analogues, 9-11, were prepared and oxidized to the aldehydes 6-8 under Swern conditions. Treatment of these alpha-hydroxy aldehydes with TBSOTf and a hindered base gave the products of an intramolecular Prins double cyclization, namely the 7-(silyloxy)-2-oxabicyclo[2.2.1]heptanes, 17-19, in 84-92% yield. These compounds were formed as single diastereomers with only the anti silyl ethers being obtained. The cyclizations occur when five-membered rings are being formed and when the initially formed cation is highly stabilized. Other substrates do not cyclize, e.g., when the alpha-hydroxy aldehydes 20-22, prepared from 26-28, are treated under similar conditions, none of the corresponding cyclization products, 23-25, were obtained.

  DOI：

  10.1021/jo971337v
• 作为产物：
  描述：

  1-(Tetrahydro-furan-2-yloxy)-propan-2-one 、 (E)-(4-phenylbut-3-en-1-yl)magnesium bromide 在 溶剂黄146 作用下， 生成 (E)-2-methyl-6-phenyl-5-hexene-1,2-diol
  参考文献：
  名称：

  An Intramolecular Prins Double Cyclization Catalyzed by Silyl Triflates¹

  摘要：

  Several intramolecular Prins double cyclizations are reported. The 2-alkyl 5-hepten-1,2-diols and their analogues, 9-11, were prepared and oxidized to the aldehydes 6-8 under Swern conditions. Treatment of these alpha-hydroxy aldehydes with TBSOTf and a hindered base gave the products of an intramolecular Prins double cyclization, namely the 7-(silyloxy)-2-oxabicyclo[2.2.1]heptanes, 17-19, in 84-92% yield. These compounds were formed as single diastereomers with only the anti silyl ethers being obtained. The cyclizations occur when five-membered rings are being formed and when the initially formed cation is highly stabilized. Other substrates do not cyclize, e.g., when the alpha-hydroxy aldehydes 20-22, prepared from 26-28, are treated under similar conditions, none of the corresponding cyclization products, 23-25, were obtained.

  DOI：

  10.1021/jo971337v