2-((E)-But-2-enyl)-4,4,5,5-tetramethyl-2-[((E)-propenyl)oxy]-[1,3,2]dioxasilolane | 467245-96-1

• 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: 2-((E)-But-2-enyl)-4,4,5,5-tetramethyl-2-[((E)-propenyl)oxy]-[1,3,2]dioxasilolane
• 英文别名: 2-[(E)-but-2-enyl]-4,4,5,5-tetramethyl-2-[(E)-prop-1-enoxy]-1,3,2-dioxasilolane
• CAS: 467245-96-1
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: JGXOBINLHWXSHE-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  环己烷基甲醛 、 2-((E)-But-2-enyl)-4,4,5,5-tetramethyl-2-[((E)-propenyl)oxy]-[1,3,2]dioxasilolane 以 苯 为溶剂， 反应 132.0h， 以60%的产率得到(1R,2S,3R,4S)-1-Cyclohexyl-2,4-dimethyl-hex-5-ene-1,3-diol
  参考文献：
  名称：

  Strained Silacycles in Organic Synthesis:  The Tandem Aldol−Allylation Reaction

  摘要：

  Allyl(crotyl)enolsilanes, when constrained in a five-membered ring with a 1,2-diol, react with aldehydes in a tandem aldol-allylation reaction to give polyketide fragments. These experimentally trivial and efficient reactions establish two new carbon-carbon bonds and up to four new stereocenters. The silane reagents, which owe their reactivity to strain release Lewis acidity, are easily prepared and stable to storage.

  DOI：

  10.1021/ja027655f
• 作为产物：
  描述：

  2-((E)-But-2-enyl)-2-chloro-4,4,5,5-tetramethyl-[1,3,2]dioxasilolane 、 (E)-1-<(trimethylsilyl)oxy>propene 在 甲基锂 作用下， 以 乙醚 为溶剂， 生成 2-((E)-But-2-enyl)-4,4,5,5-tetramethyl-2-[((E)-propenyl)oxy]-[1,3,2]dioxasilolane
  参考文献：
  名称：

  Strained Silacycles in Organic Synthesis:  The Tandem Aldol−Allylation Reaction

  摘要：

  Allyl(crotyl)enolsilanes, when constrained in a five-membered ring with a 1,2-diol, react with aldehydes in a tandem aldol-allylation reaction to give polyketide fragments. These experimentally trivial and efficient reactions establish two new carbon-carbon bonds and up to four new stereocenters. The silane reagents, which owe their reactivity to strain release Lewis acidity, are easily prepared and stable to storage.

  DOI：

  10.1021/ja027655f

文献信息

• Strained Silacycles in Organic Synthesis:  The Tandem Aldol−Allylation Reaction
  作者：Xiaolun Wang、Qinglin Meng、Andrew J. Nation、James L. Leighton

  DOI：10.1021/ja027655f

  日期：2002.9.1

  Allyl(crotyl)enolsilanes, when constrained in a five-membered ring with a 1,2-diol, react with aldehydes in a tandem aldol-allylation reaction to give polyketide fragments. These experimentally trivial and efficient reactions establish two new carbon-carbon bonds and up to four new stereocenters. The silane reagents, which owe their reactivity to strain release Lewis acidity, are easily prepared and stable to storage.