[1-(trimethylsilyl)cycloprop-2-en-1-yl]methyl 3,3-dimethylacrylate | 682760-67-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [1-(trimethylsilyl)cycloprop-2-en-1-yl]methyl 3,3-dimethylacrylate
• 英文别名: (1-Trimethylsilylcycloprop-2-en-1-yl)methyl 3-methylbut-2-enoate
• CAS: 682760-67-4
• 化学式: C₁₂H₂₀O₂Si
• 分子量: 224.375
• InChiKey: PNLVDSUZNVAGKL-UHFFFAOYSA-N

物化性质

• 沸点：
  258.1±15.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲基锡 、 [1-(trimethylsilyl)cycloprop-2-en-1-yl]methyl 3,3-dimethylacrylate 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到[(1R,2S)-1-trimethylsilyl-2-trimethylstannylcyclopropyl]methyl 3-methylbut-2-enoate
  参考文献：
  名称：

  Catalytic Enantioselective Hydrostannation of Cyclopropenes

  摘要：

  The first examples of catalytic enantioselective hydrostannation of the C=C double bond of cyclopropenes has been demonstrated. This method allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and enantioselectivity. The facial selectivity of this reaction is entirely controlled by steric factors. A variety of functional groups at C-3 of the cyclopropenes were tolerated.

  DOI：

  10.1021/ja0496928
• 作为产物：
  描述：

  3-carbomethoxy-3-(trimethylsilyl)cyclopropene 在 吡啶 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 [1-(trimethylsilyl)cycloprop-2-en-1-yl]methyl 3,3-dimethylacrylate
  参考文献：
  名称：

  Catalytic Enantioselective Hydrostannation of Cyclopropenes

  摘要：

  The first examples of catalytic enantioselective hydrostannation of the C=C double bond of cyclopropenes has been demonstrated. This method allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and enantioselectivity. The facial selectivity of this reaction is entirely controlled by steric factors. A variety of functional groups at C-3 of the cyclopropenes were tolerated.

  DOI：

  10.1021/ja0496928

文献信息

• Catalytic Enantioselective Hydrostannation of Cyclopropenes
  作者：Marina Rubina、Michael Rubin、Vladimir Gevorgyan

  DOI：10.1021/ja0496928

  日期：2004.3.1

  The first examples of catalytic enantioselective hydrostannation of the C=C double bond of cyclopropenes has been demonstrated. This method allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and enantioselectivity. The facial selectivity of this reaction is entirely controlled by steric factors. A variety of functional groups at C-3 of the cyclopropenes were tolerated.