(3E)-4-[allyl(dimethyl)silyl]-1-phenylbut-3-en-1-ol | 909556-18-9

• 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: (3E)-4-[allyl(dimethyl)silyl]-1-phenylbut-3-en-1-ol
• 英文别名: (E)-4-[dimethyl(prop-2-enyl)silyl]-1-phenylbut-3-en-1-ol
• CAS: 909556-18-9
• 化学式: C₁₅H₂₂OSi
• 分子量: 246.425
• InChiKey: ZRESXHKSNOKSQR-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3E)-4-[allyl(dimethyl)silyl]-1-phenylbut-3-en-1-ol 、 4-碘代苯乙酮 在 tris(dibenzylideneacetone)dipalladium (0) 、 乙醇 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 以84%的产率得到1-{4-[(1E)-4-hydroxy-4-phenylbut-1-en-1-yl]phenyl}ethanone
  参考文献：
  名称：

  All-Carbon-Substituted Vinylsilane Stable to TBAF:  Synthesis of Allyldimethylvinylsilane and Its Pd-Catalyzed Cross-Coupling under Mild Conditions

  摘要：

  Allyldimethylvinylsilanes 3 are easily synthesized by the reaction of silylallylmetals, generated from 1 by n-BuLi/t-BuOK, with carbonyl compounds in the absence or presence of metal halides. They can tolerate 2 equiv of TBAF in THF at room temperature for at least 6 h but can be easily activated in the presence of a palladium catalyst and TBAF to perform the cross-coupling reaction with aryl iodides at room temperature.

  DOI：

  10.1021/ol061288l
• 作为产物：
  描述：

  二烯丙基二甲基硅烷 、 苯甲醛 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以67%的产率得到(3E)-4-[allyl(dimethyl)silyl]-1-phenylbut-3-en-1-ol
  参考文献：
  名称：

  All-Carbon-Substituted Vinylsilane Stable to TBAF:  Synthesis of Allyldimethylvinylsilane and Its Pd-Catalyzed Cross-Coupling under Mild Conditions

  摘要：

  Allyldimethylvinylsilanes 3 are easily synthesized by the reaction of silylallylmetals, generated from 1 by n-BuLi/t-BuOK, with carbonyl compounds in the absence or presence of metal halides. They can tolerate 2 equiv of TBAF in THF at room temperature for at least 6 h but can be easily activated in the presence of a palladium catalyst and TBAF to perform the cross-coupling reaction with aryl iodides at room temperature.

  DOI：

  10.1021/ol061288l

文献信息

• All-Carbon-Substituted Vinylsilane Stable to TBAF:  Synthesis of Allyldimethylvinylsilane and Its Pd-Catalyzed Cross-Coupling under Mild Conditions
  作者：Lianhai Li、Neenah Navasero

  DOI：10.1021/ol061288l

  日期：2006.8.1

  Allyldimethylvinylsilanes 3 are easily synthesized by the reaction of silylallylmetals, generated from 1 by n-BuLi/t-BuOK, with carbonyl compounds in the absence or presence of metal halides. They can tolerate 2 equiv of TBAF in THF at room temperature for at least 6 h but can be easily activated in the presence of a palladium catalyst and TBAF to perform the cross-coupling reaction with aryl iodides at room temperature.