1-(2-(trimethylsilyl)ethyl)but-2-yne ether | 1352803-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(trimethylsilyl)ethyl)but-2-yne ether
• CAS: 1352803-61-2
• 化学式: C₉H₁₈OSi
• 分子量: 170.327
• InChiKey: BNXTWJHPQMAVKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(2-(trimethylsilyl)ethyl)but-2-yne ether 在 喹啉 、 5% Pd-BaSO4 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到1-(2-(trimethylsilyl)ethyl)but-2(Z)-ene
  参考文献：
  名称：

  Intermolecular Oxonium Ylide Mediated Synthesis of Medium-Sized Oxacycles

  摘要：

  Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

  DOI：

  10.1021/ol203129d
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 1-溴-2-丁炔 在 sodium hydride 、 sodium iodide 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以94%的产率得到1-(2-(trimethylsilyl)ethyl)but-2-yne ether
  参考文献：
  名称：

  Intermolecular Oxonium Ylide Mediated Synthesis of Medium-Sized Oxacycles

  摘要：

  Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

  DOI：

  10.1021/ol203129d