[(3-Benzylhex-1-yn-1-yl)oxy]tri(propan-2-yl)silane | 765906-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3-Benzylhex-1-yn-1-yl)oxy]tri(propan-2-yl)silane
• 英文别名: 3-benzylhex-1-ynoxy-tri(propan-2-yl)silane
• CAS: 765906-56-7
• 化学式: C₂₂H₃₆OSi
• 分子量: 344.613
• InChiKey: CGVBOQQORBJSNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  399.6±35.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(3-Benzylhex-1-yn-1-yl)oxy]tri(propan-2-yl)silane 在 双三氟甲烷磺酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到Triisopropyl-((R)-3-propyl-3,4-dihydro-naphthalen-1-yloxy)-silane
  参考文献：
  名称：

  Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes

  摘要：

  We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.

  DOI：

  10.1021/ja046586x
• 作为产物：
  描述：

  5-benzyl-2-methyloct-3-yn-2-ol 在 氢氧化钾 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 11.0h， 生成 [(3-Benzylhex-1-yn-1-yl)oxy]tri(propan-2-yl)silane
  参考文献：
  名称：

  Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes

  摘要：

  We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.

  DOI：

  10.1021/ja046586x

文献信息

• Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes
  作者：Liming Zhang、Sergey A. Kozmin

  DOI：10.1021/ja046586x

  日期：2004.8.1

  We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.