5,7,7-trimethylspiro[2.4]heptan-5-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,7,7-trimethylspiro[2.4]heptan-5-ol
• 英文别名: 5,7,7-Trimethylspiro[2.4]heptan-5-ol
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: QLTQHKGIKKXGKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 在 三甲基铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 5,7,7-trimethylspiro[2.4]heptan-5-ol
  参考文献：
  名称：

  Spiro-Cyclopropanation from Oxoallylsilanes

  摘要：

  A novel highly stereoselective spiro-cyclopropanation reaction from oxoallylsilanes is described. Oxoallylsilanes are readily obtained by silylcupration of allene followed by conjugate addition to enones. The former oxoallylsilanes undergo a tandem cyclization-cyclopropanation reaction when treated with CH2I2/Me3Al, leading to hydroxylated polycyclic systems bearing the spiro-cyclopropane moiety. The scope of the process is studied, and a feasible pathway is discussed.

  DOI：

  10.1021/ja051967b

文献信息

• Spiro-Cyclopropanation from Oxoallylsilanes
  作者：Asunción Barbero、Pilar Castreño、Francisco J. Pulido

  DOI：10.1021/ja051967b

  日期：2005.6.1

  A novel highly stereoselective spiro-cyclopropanation reaction from oxoallylsilanes is described. Oxoallylsilanes are readily obtained by silylcupration of allene followed by conjugate addition to enones. The former oxoallylsilanes undergo a tandem cyclization-cyclopropanation reaction when treated with CH2I2/Me3Al, leading to hydroxylated polycyclic systems bearing the spiro-cyclopropane moiety. The scope of the process is studied, and a feasible pathway is discussed.