3-hydroxymethyl-3-(trimethylsilyl)cyclopropene | 232269-56-6

• 分子结构分类: 有机化合物
• 英文名称: 3-hydroxymethyl-3-(trimethylsilyl)cyclopropene
• 英文别名: (1-trimethylsilylcycloprop-2-en-1-yl)methanol
• CAS: 232269-56-6
• 化学式: C₇H₁₄OSi
• 分子量: 142.273
• InChiKey: NXZKLHUSYHYBRO-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 200 Torr)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-hydroxymethyl-3-(trimethylsilyl)cyclopropene 在 草酰氯 、 二甲基十二/十四烷基叔胺 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到3-formyl-3-(trimethylsilyl)cyclopropene
  参考文献：
  名称：

  3-取代的3-三甲基甲硅烷基环丙烯的合成和热解

  摘要：

  描述了3-取代的-3-（三甲基甲硅烷基）环丙烯（X ＝ CO 2 Et，CHO，CN）的合成。探讨了它们的酸敏感性和热稳定性，并鉴定了反应产物。在一种情况下，可能涉及到杜瓦呋喃的新颖重排，并且通过动力学和计算探索了该途径。

  DOI：

  10.1016/s0040-4020(99)00276-8
• 作为产物：
  描述：

  3-carbomethoxy-3-(trimethylsilyl)cyclopropene 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以85%的产率得到3-hydroxymethyl-3-(trimethylsilyl)cyclopropene
  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

• Enantioselective, Facially Selective Carbomagnesation of Cyclopropenes
  作者：Xiaozhong Liu、Joseph M. Fox

  DOI：10.1021/ja058101q

  日期：2006.5.1

  Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step.