(E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]-1-phenylprop-2-enol | 514797-29-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]-1-phenylprop-2-enol
• 英文别名: (E)-3-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]-1-phenylprop-2-en-1-ol
• CAS: 514797-29-6
• 化学式: C₂₁H₂₈O₂Si
• 分子量: 340.538
• InChiKey: XPHLARVCJJQMPG-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]-1-phenylprop-2-enol 在 吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 bis(diphenylphosphino)butane 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 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：

  (E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enol 在 manganese(IV) oxide 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]-1-phenylprop-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

• PALLADIUM(0)-CATALYZED SYNTHESIS OF 2-PHENYL-<i>2H</i>-CHROMENE
  作者：J.-R. Labrosse、P. Lhoste、D. Sinou

  DOI：10.1081/scc-120014986

  日期：2002.1

  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.