1-cyclopropyl-1-(dimethyl(phenyl)silyl)hept-2-yn-1-ol

• 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: 1-cyclopropyl-1-(dimethyl(phenyl)silyl)hept-2-yn-1-ol
• 英文别名: 1-Cyclopropyl-1-[dimethyl(phenyl)silyl]hept-2-yn-1-ol；1-cyclopropyl-1-[dimethyl(phenyl)silyl]hept-2-yn-1-ol
• 化学式: C₁₈H₂₆OSi
• 分子量: 286.489
• InChiKey: DCDXGOSGMCSAQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  cyclopropyl(dimethyl(phenyl)silyl)methanone 、 1-己炔 在 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以93%的产率得到1-cyclopropyl-1-(dimethyl(phenyl)silyl)hept-2-yn-1-ol
  参考文献：
  名称：

  Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions

  摘要：

  Silyloxyallenes derived from alpha-hydroxypropargylsilanes undergo efficient addition to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2' process. Enantioenriched propargylsilanes are synthesized by a new zinc-promoted addition of alkynes to acylsilanes in up to 74% ee. This work demonstrates that conversion to the silyloxyallenes occurs with minimal erosion in optical activity. The use of a chiral chromium(III) Lewis acid effects the catalytic asymmetric addition of racemic silyloxyallenes to aromatic aldehydes in up to 92% ee. The overall reaction is broad in scope and accommodates a wide variety of aromatic and aliphatic substituents on both the propargylsilane and aldehyde.

  DOI：

  10.1021/ja0653674

文献信息

• Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions
  作者：Troy E. Reynolds、Ashwin R. Bharadwaj、Karl A. Scheidt

  DOI：10.1021/ja0653674

  日期：2006.12.1

  Silyloxyallenes derived from alpha-hydroxypropargylsilanes undergo efficient addition to aldehydes with catalytic amounts of Lewis acids. The allenes are accessed from the corresponding propargylsilanes in a base-catalyzed 1,2-Brook rearrangement/SE2' process. Enantioenriched propargylsilanes are synthesized by a new zinc-promoted addition of alkynes to acylsilanes in up to 74% ee. This work demonstrates that conversion to the silyloxyallenes occurs with minimal erosion in optical activity. The use of a chiral chromium(III) Lewis acid effects the catalytic asymmetric addition of racemic silyloxyallenes to aromatic aldehydes in up to 92% ee. The overall reaction is broad in scope and accommodates a wide variety of aromatic and aliphatic substituents on both the propargylsilane and aldehyde.