(2S)-1-Ethoxy-2-methoxy-1-(trimethylsiloxy)propane

• 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: (2S)-1-Ethoxy-2-methoxy-1-(trimethylsiloxy)propane
• 英文别名: [(2S)-1-ethoxy-2-methoxypropoxy]-trimethylsilane
• 化学式: C₉H₂₂O₃Si
• 分子量: 206.357
• InChiKey: OROMCXMHXWGTMR-IENPIDJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• 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：

  (2S)-1-Ethoxy-2-methoxy-1-(trimethylsiloxy)propane 、 烯丙基三甲基硅烷 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,3R)-2-Methoxy-5-hexen-3-ol 、 (2S,2S)-2-Methoxy-5-hexen-3-ol
  参考文献：
  名称：

  Preparation of Monosilyl Acetals from Esters via iBu2AlH Reduction and Trapping with N-(Trimethylsilyl)imidazole. Addition of Allyltrimethylsilane To Yield Homoallylic Alcohols or Ethers

  摘要：

  Alkyl esters were reduced with iBu(2)AlH or a 1:1 mixture of iBu(2)AlH and iBu(3)Al (iBu(2)AlH . iBu(3)Al or iBu(5)Al(2)H), followed by trapping of the resulting tetrahedral intermediate with TMS-imidazole to produce monosilyl acetals. Reaction of the mixed acetals with allyltrimethylsilane in the presence of Lewis acids (Hosomi-Sakurai reaction) generated homoallylic alcohols or ethers selectively, depending on the substitution of the monosilyl acetal. TMS methoxy acetals (MeO-CH-OTMS) and TMS ethoxy acetals bearing additional complexing groups such as MeO- or Ph(2)C=N- provided alcohols with 1.5:1-9:1 threoselectivity, while simple TMS ethoxy acetals provided only ethyl ethers as products. The monosilyl acetal configuration was easily epimerized or racemized, and the configuration of the Hosomi-Sakurai product was apparently independent of the initial monosilyl acetal reactant configuration.

  DOI：

  10.1021/jo00112a039
• 作为产物：
  描述：

  S)-(-)-2-甲氧基丙酸乙酯 、 三甲基硅咪唑 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(2S)-1-Ethoxy-2-methoxy-1-(trimethylsiloxy)propane
  参考文献：
  名称：

  Preparation of Monosilyl Acetals from Esters via iBu2AlH Reduction and Trapping with N-(Trimethylsilyl)imidazole. Addition of Allyltrimethylsilane To Yield Homoallylic Alcohols or Ethers

  摘要：

  Alkyl esters were reduced with iBu(2)AlH or a 1:1 mixture of iBu(2)AlH and iBu(3)Al (iBu(2)AlH . iBu(3)Al or iBu(5)Al(2)H), followed by trapping of the resulting tetrahedral intermediate with TMS-imidazole to produce monosilyl acetals. Reaction of the mixed acetals with allyltrimethylsilane in the presence of Lewis acids (Hosomi-Sakurai reaction) generated homoallylic alcohols or ethers selectively, depending on the substitution of the monosilyl acetal. TMS methoxy acetals (MeO-CH-OTMS) and TMS ethoxy acetals bearing additional complexing groups such as MeO- or Ph(2)C=N- provided alcohols with 1.5:1-9:1 threoselectivity, while simple TMS ethoxy acetals provided only ethyl ethers as products. The monosilyl acetal configuration was easily epimerized or racemized, and the configuration of the Hosomi-Sakurai product was apparently independent of the initial monosilyl acetal reactant configuration.

  DOI：

  10.1021/jo00112a039

文献信息

• Preparation of Monosilyl Acetals from Esters via iBu2AlH Reduction and Trapping with N-(Trimethylsilyl)imidazole. Addition of Allyltrimethylsilane To Yield Homoallylic Alcohols or Ethers
  作者：Dalibor Sames、Yunqi Liu、Lynn DeYoung、Robin Polt

  DOI：10.1021/jo00112a039

  日期：1995.4

  Alkyl esters were reduced with iBu(2)AlH or a 1:1 mixture of iBu(2)AlH and iBu(3)Al (iBu(2)AlH . iBu(3)Al or iBu(5)Al(2)H), followed by trapping of the resulting tetrahedral intermediate with TMS-imidazole to produce monosilyl acetals. Reaction of the mixed acetals with allyltrimethylsilane in the presence of Lewis acids (Hosomi-Sakurai reaction) generated homoallylic alcohols or ethers selectively, depending on the substitution of the monosilyl acetal. TMS methoxy acetals (MeO-CH-OTMS) and TMS ethoxy acetals bearing additional complexing groups such as MeO- or Ph(2)C=N- provided alcohols with 1.5:1-9:1 threoselectivity, while simple TMS ethoxy acetals provided only ethyl ethers as products. The monosilyl acetal configuration was easily epimerized or racemized, and the configuration of the Hosomi-Sakurai product was apparently independent of the initial monosilyl acetal reactant configuration.