tert-Butyl-dimethyl-(2-vinyloxy-oct-3-ynyloxy)-silane | 825627-92-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-Butyl-dimethyl-(2-vinyloxy-oct-3-ynyloxy)-silane
• 英文别名: tert-Butyl{[2-(ethenyloxy)oct-3-yn-1-yl]oxy}dimethylsilane；tert-butyl-(2-ethenoxyoct-3-ynoxy)-dimethylsilane
• CAS: 825627-92-7
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: RNAVSTDMBRSKEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-Butyl-dimethyl-(2-vinyloxy-oct-3-ynyloxy)-silane 在 tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到4-Butyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-2-ol
  参考文献：
  名称：

  Gold(I)-Catalyzed Synthesis of Dihydropyrans

  摘要：

  A trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, serves as the catalyst for the stereocontrolled synthesis of 2-hydroxy-3,6-dihydropyrans from propargyl vinyl ethers. Importantly, the rearrangement proceeds with excellent diastereoselectivity, and the rearrangement of chiral nonracemic propargyl vinyl ethers proceeds with excellent chirality transfer to furnish enantioenriched pyrans. Additionally, the reaction is amenable to the synthesis of spiroketals from appropriately functionalized precursors. In this case, from a linear precursor, in a single step, the bicyclic spiroketal framework is established with complete stereocontrol over three centers and an alkene functional group in the product.

  DOI：

  10.1021/ja061344d

文献信息

• Gold(I)-Catalyzed Propargyl Claisen Rearrangement
  作者：Benjamin D. Sherry、F. Dean Toste

  DOI：10.1021/ja044602k

  日期：2004.12.1

  alcohols are prepared from propargyl vinyl ethers using a trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, as a catalyst for propargyl Claisen rearrangement at room temperature. The gold(I)-catalyzed reaction is effective for a diverse collection of propargyl vinyl ethers, including substrates containing aryl and alkyl groups at the propargylic position, and hydrogen, aryl, and alkyl substituents at the alkyne

  使用三核金 (I)-氧代配合物 [(Ph3PAu)3O]BF4 作为炔丙基 Claisen 重排的催化剂，由炔丙基乙烯基醚制备高丙醇。金 (I) 催化的反应对炔丙基乙烯基醚的多种集合有效，包括在炔丙基位置含有芳基和烷基的底物，以及在炔末端含有氢、芳基和烷基取代基的底物。可以在反应中使用叔炔丙基乙烯基醚，在稍微升高的温度下，以提供四取代的丙二烯。重要的是，1,2-二取代乙烯基醚的重排具有极好的非对映选择性，手性非外消旋炔丙基乙烯基醚的重排具有极好的手性转移，以​​提供对映体富集的丙二烯。
• Gold(I)-Catalyzed Synthesis of Dihydropyrans
  作者：Benjamin D. Sherry、Lisa Maus、Brian Ngo Laforteza、F. Dean Toste

  DOI：10.1021/ja061344d

  日期：2006.6.1

  A trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, serves as the catalyst for the stereocontrolled synthesis of 2-hydroxy-3,6-dihydropyrans from propargyl vinyl ethers. Importantly, the rearrangement proceeds with excellent diastereoselectivity, and the rearrangement of chiral nonracemic propargyl vinyl ethers proceeds with excellent chirality transfer to furnish enantioenriched pyrans. Additionally, the reaction is amenable to the synthesis of spiroketals from appropriately functionalized precursors. In this case, from a linear precursor, in a single step, the bicyclic spiroketal framework is established with complete stereocontrol over three centers and an alkene functional group in the product.