[2S,5R]-2-(3'-phenyldimethylsilylmethyl-2'-methylbut-3'-en-2-yl)-5-methylcyclohexanone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [2S,5R]-2-(3'-phenyldimethylsilylmethyl-2'-methylbut-3'-en-2-yl)-5-methylcyclohexanone
• 英文别名: (2S,5R)-2-[3-[[dimethyl(phenyl)silyl]methyl]-2-methylbut-3-en-2-yl]-5-methylcyclohexan-1-one
• 化学式: C₂₁H₃₂OSi
• 分子量: 328.57
• InChiKey: CBGQTFDYIVTVHT-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [2S,5R]-2-(3'-phenyldimethylsilylmethyl-2'-methylbut-3'-en-2-yl)-5-methylcyclohexanone 、 二碘甲烷 在 二碘甲烷 、 三甲基铝 、 水 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 48.5h， 以79%的产率得到[1S,3S,6S]-3,7,7-trimethyl-8-spirocyclopropyl-bicyclo[4.3.0]nonan-1-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
• 作为产物：
  描述：

  长叶薄荷酮 、 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以82%的产率得到[2S,5R]-2-(3'-phenyldimethylsilylmethyl-2'-methylbut-3'-en-2-yl)-5-methylcyclohexanone
  参考文献：
  名称：

  Barbero, Asuncion; Castreno, Pilar; Pulido, Francisco J., ARKIVOC, 2010, vol. 2010, # 3, p. 274 - 287

  摘要：

  DOI：

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.
• Barbero, Asuncion; Castreno, Pilar; Pulido, Francisco J., ARKIVOC, 2010, vol. 2010, # 3, p. 274 - 287
  作者：Barbero, Asuncion、Castreno, Pilar、Pulido, Francisco J.、Val, Patricia、Gonzalez-Ortega, Alfonso、Sanudo, M. Carmen

  DOI：——

  日期：——