(E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enol | 514797-25-2

• 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)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enol
• 英文别名: (E)-3-(2-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol；(E)-3-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-en-1-ol
• CAS: 514797-25-2
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: WMBMKOIOIZDCBB-CSKARUKUSA-N

物化性质

• 沸点：
  338.8±30.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enol 在 吡啶 、 manganese(IV) oxide 、 tris(dibenzylideneacetone)dipalladium (0) 、 bis(diphenylphosphino)butane 、 四丁基氟化铵 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2-phenylchromene
  参考文献：
  名称：

  PALLADIUM(0)-CATALYZED SYNTHESIS OF 2-PHENYL-2H-CHROMENE

  摘要：

  2-Phenyl-2H-chromene is obtained in quite good yield starting from 3-[(2-tert-butyldimethylsilyl)oxyphenyl]prop-2-enal. Condensation of this aldehyde with phenyl magnesium bromide, followed by the acetylation of the alcohol obtained, and then intramolecular cyclization in the presence of a palladium catalyst gave the phenylchromene in an overall 34% yield.

  DOI：

  10.1081/scc-120014986
• 作为产物：
  描述：

  ethyl (E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enoate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以94%的产率得到(E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enol
  参考文献：
  名称：

  PALLADIUM(0)-CATALYZED SYNTHESIS OF 2-PHENYL-2H-CHROMENE

  摘要：

  2-Phenyl-2H-chromene is obtained in quite good yield starting from 3-[(2-tert-butyldimethylsilyl)oxyphenyl]prop-2-enal. Condensation of this aldehyde with phenyl magnesium bromide, followed by the acetylation of the alcohol obtained, and then intramolecular cyclization in the presence of a palladium catalyst gave the phenylchromene in an overall 34% yield.

  DOI：

  10.1081/scc-120014986

文献信息

• Facile Synthesis of <i>Z</i>-Alkenes via Uphill Catalysis
  作者：Kamaljeet Singh、Shannon J. Staig、Jimmie D. Weaver

  DOI：10.1021/ja5019749

  日期：2014.4.9

  Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.