Triethyl-(5-ethyl-2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-silane | 444816-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Triethyl-(5-ethyl-2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-silane
• 英文别名: Triethyl-[(5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methoxy]silane
• CAS: 444816-10-8
• 化学式: C₁₅H₃₂O₃Si
• 分子量: 288.503
• InChiKey: KEQZWFMTFIMBRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Triethyl-(5-ethyl-2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-silane 在 咪唑 、 水 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 tert-Butyl-(5-ethyl-2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-dimethyl-silane
  参考文献：
  名称：

  Facile Cleavage of Triethylsilyl (TES) Ethers Using o-Iodoxybenzoic Acid (IBX) without Affecting tert-Butyldimethylsilyl (TBS) Ethers

  摘要：

  [GRAPHICS]In DMSO cleavage of triethylsilyl (TES) ethers by o-iodoxybenzoic acid (IBX) was significantly faster than cleavage of tart-butyldimethylsilyl (TBS) ethers or further oxidation into carbonyl compounds. In most cases, TES protecting groups could be removed in good to excellent yields within 1 h, whereas similar TBS protecting groups remained intact under the same conditions. The procedure also could be adapted for direct one-pot conversion of TES ethers into carbonyl compounds.

  DOI：

  10.1021/ol025946n
• 作为产物：
  描述：

  三乙基氯硅烷 、 (5-ethyl-2,2-dimethyl-1,3-dioxan-5-yl)methanol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42.8%的产率得到Triethyl-(5-ethyl-2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-silane
  参考文献：
  名称：

  Facile Cleavage of Triethylsilyl (TES) Ethers Using o-Iodoxybenzoic Acid (IBX) without Affecting tert-Butyldimethylsilyl (TBS) Ethers

  摘要：

  [GRAPHICS]In DMSO cleavage of triethylsilyl (TES) ethers by o-iodoxybenzoic acid (IBX) was significantly faster than cleavage of tart-butyldimethylsilyl (TBS) ethers or further oxidation into carbonyl compounds. In most cases, TES protecting groups could be removed in good to excellent yields within 1 h, whereas similar TBS protecting groups remained intact under the same conditions. The procedure also could be adapted for direct one-pot conversion of TES ethers into carbonyl compounds.

  DOI：

  10.1021/ol025946n