ethyl 2,2-diethoxy-3-trimethylsilylcyclopropane-1-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,2-diethoxy-3-trimethylsilylcyclopropane-1-carboxylate
• 英文别名: ethyl (1R,3R)-2,2-diethoxy-3-trimethylsilylcyclopropane-1-carboxylate
• 化学式: C₁₃H₂₆O₄Si
• 分子量: 274.433
• InChiKey: CMRNVBSRYFHUAP-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-diethoxy-3-trimethylsilylcyclopropane-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以68%的产率得到(2,2-diethoxy-3-trimethylsilylcyclopropyl)methanol
  参考文献：
  名称：

  Trimethylsilyketene dialkylacetals in organic synthesis: Reactions with alkyldiazoacetates

  摘要：

  The reaction of trimethylsilylketene dialkylacetals with alkyldiazoacetates in the presence of Cu(acac)(2) or Rh-2(OAc)(4) results in the formation of alkyl-2,2-dialkoxy-3-trimethylsilylcyclopropane-1-carboxylates 3-8. The cycloaddition proceeds stereoselectively, giving exclusively one of two possible diastereomers. Compounds 4 and 6 are transformed by reaction with LiAIH(4), to cyclopropylmethanols 9 and 10 in high yields. All compounds have been characterized by elemental analyses, H-1, C-13 NMR and IR spectroscopy.

  DOI：

  10.1016/s0022-328x(96)06504-7
• 作为产物：
  描述：

  重氮乙酸乙酯 、 2,2-二乙氧基乙烯基(三甲基)硅烷 在 dirhodium tetracetate dihydrate 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以76%的产率得到ethyl 2,2-diethoxy-3-trimethylsilylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Trimethylsilyketene dialkylacetals in organic synthesis: Reactions with alkyldiazoacetates

  摘要：

  The reaction of trimethylsilylketene dialkylacetals with alkyldiazoacetates in the presence of Cu(acac)(2) or Rh-2(OAc)(4) results in the formation of alkyl-2,2-dialkoxy-3-trimethylsilylcyclopropane-1-carboxylates 3-8. The cycloaddition proceeds stereoselectively, giving exclusively one of two possible diastereomers. Compounds 4 and 6 are transformed by reaction with LiAIH(4), to cyclopropylmethanols 9 and 10 in high yields. All compounds have been characterized by elemental analyses, H-1, C-13 NMR and IR spectroscopy.

  DOI：

  10.1016/s0022-328x(96)06504-7

文献信息

• Trimethylsilyketene dialkylacetals in organic synthesis: Reactions with alkyldiazoacetates
  作者：Galina S. Zaitseva、Ol'ga P. Novikova、Evgeny V. Grigoriev、Alexander V. Kisin、Evgeni V. Avtomonov、Jörg Lorberth

  DOI：10.1016/s0022-328x(96)06504-7

  日期：1996.11

  The reaction of trimethylsilylketene dialkylacetals with alkyldiazoacetates in the presence of Cu(acac)(2) or Rh-2(OAc)(4) results in the formation of alkyl-2,2-dialkoxy-3-trimethylsilylcyclopropane-1-carboxylates 3-8. The cycloaddition proceeds stereoselectively, giving exclusively one of two possible diastereomers. Compounds 4 and 6 are transformed by reaction with LiAIH(4), to cyclopropylmethanols 9 and 10 in high yields. All compounds have been characterized by elemental analyses, H-1, C-13 NMR and IR spectroscopy.