(E,E)-[4-(benzyldimethylsilyl)-1,3-butadienyl]dimethylsilanol | 857350-04-0

• 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)-[4-(benzyldimethylsilyl)-1,3-butadienyl]dimethylsilanol
• 英文别名: 1-dimethylhydroxysilyl-4-benzyldimethylsilyl-1,3-butadiene；benzyl-[(1E,3E)-4-[hydroxy(dimethyl)silyl]buta-1,3-dienyl]-dimethylsilane
• CAS: 857350-04-0
• 化学式: C₁₅H₂₄OSi₂
• 分子量: 276.526
• InChiKey: CVOZQIOXMYVCIV-QHKWOANTSA-N

物化性质

• 沸点：
  170 °C(Press: 0.1 Torr)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  18
• 可旋转键数：
  5
• 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：

  (E,E)-[4-(benzyldimethylsilyl)-1,3-butadienyl]dimethylsilanol 、 4-碘代苯乙酮 在 potassium trimethylsilonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以76%的产率得到1-[4-[(1E,3E)-4-[benzyl(dimethyl)silyl]buta-1,3-dienyl]phenyl]ethanone
  参考文献：
  名称：

  Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes

  摘要：

  A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a "one pot" procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.

  DOI：

  10.1021/ja0518373
• 作为产物：
  描述：

  苄基二甲基氯硅烷 在 甲醇 、 Wilkinson's catalyst 、 t-Bu₃P*Pt(DVDS) 、 sodium methylate 作用下， 以 四氢呋喃 、 甲苯 、 xylene 为溶剂， 反应 60.0h， 生成 (E,E)-[4-(benzyldimethylsilyl)-1,3-butadienyl]dimethylsilanol
  参考文献：
  名称：

  Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes

  摘要：

  A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a "one pot" procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.

  DOI：

  10.1021/ja0518373

文献信息

• Total Synthesis of RK-397
  作者：Scott E. Denmark、Shinji Fujimori

  DOI：10.1021/ja052226d

  日期：2005.6.1

  An enantioselective synthesis of the polyene macrolide RK-397 is described. The use of the same eight-carbon building block twice for the construction of the polyol chain allowed for a highly convergent synthesis. The synthesis highlights stereoselective vinylogous aldol addition using a chiral bisphosphoramide as well as a sequential palladium-catalyzed cross-coupling reaction for the preparation

  描述了多烯大环内酯 RK-397 的对映选择性合成。两次使用相同的八碳结构单元构建多元醇链允许高度收敛的合成。该合成突出了使用手性双磷酰胺的立体选择性乙烯基醛醇加成以及用于制备关键片段的连续钯催化交叉偶联反应。
• Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes
  作者：Scott E. Denmark、Steven A. Tymonko

  DOI：10.1021/ja0518373

  日期：2005.6.1

  A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a "one pot" procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.