2-Methoxy-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran-3-ol | 207384-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran-3-ol
• CAS: 207384-98-3
• 化学式: C₁₂H₂₂O₃Si
• 分子量: 242.39
• InChiKey: YMJKGRUIVVZMJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Methoxy-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran-3-ol 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A Reiterative Synthesis of Trans-Fused Polypyrans via Tungsten Pentacarbonyl-Promoted Alkynol Endocyclization

  摘要：

  Endocyclization of 1-alkyn-5-ols occurs in the presence of tungsten pentacarbonyl-THF complex to give cyclic six-membered tungsten oxacarbenes which are easily converted to alpha-stannyl enol ethers by treatment with Bu3SnOTf and Et3N. These stannylated dihydropyrans undergo organocuprate-mediated alkylation to provide 6-(2-propynyl)-3,4-dihydro-2H-pyrans. Oxidation of these propargylated dihydropyrans with m-CPBA followed by reduction with Et3SiH under Lewis acid conditions generates another trans-fused 1-alkyn-5-ol. Repetition of this process provides are iterative synthesis of trans-fused polypyrans.

  DOI：

  10.1021/jo980058k
• 作为产物：
  描述：

  3-(trimethylsilyl)prop-2-ynyl tosylate 在 copper(l) iodide 、 叔丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成 2-Methoxy-2-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  A Reiterative Synthesis of Trans-Fused Polypyrans via Tungsten Pentacarbonyl-Promoted Alkynol Endocyclization

  摘要：

  Endocyclization of 1-alkyn-5-ols occurs in the presence of tungsten pentacarbonyl-THF complex to give cyclic six-membered tungsten oxacarbenes which are easily converted to alpha-stannyl enol ethers by treatment with Bu3SnOTf and Et3N. These stannylated dihydropyrans undergo organocuprate-mediated alkylation to provide 6-(2-propynyl)-3,4-dihydro-2H-pyrans. Oxidation of these propargylated dihydropyrans with m-CPBA followed by reduction with Et3SiH under Lewis acid conditions generates another trans-fused 1-alkyn-5-ol. Repetition of this process provides are iterative synthesis of trans-fused polypyrans.

  DOI：

  10.1021/jo980058k