4,4,5,5-tetramethyl-2-[(Z)-prop-1-enoxy]-2-prop-2-enyl-1,3,2-dioxasilolane | 467245-81-4

• 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: 4,4,5,5-tetramethyl-2-[(Z)-prop-1-enoxy]-2-prop-2-enyl-1,3,2-dioxasilolane
• CAS: 467245-81-4
• 化学式: C₁₂H₂₂O₃Si
• 分子量: 242.39
• InChiKey: JOBPHSSWXPWQRX-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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 、 4,4,5,5-tetramethyl-2-[(Z)-prop-1-enoxy]-2-prop-2-enyl-1,3,2-dioxasilolane 以 甲苯 为溶剂， 反应 60.0h， 以38%的产率得到
  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：

  (Z)-(Propenyloxy)trimethylsilane 、 2-Allyl-2-chloro-4,4,5,5-tetramethyl-[1,3,2]dioxasilolane 在 甲基锂 作用下， 以 乙醚 为溶剂， 生成 4,4,5,5-tetramethyl-2-[(Z)-prop-1-enoxy]-2-prop-2-enyl-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.