2-Methyl-4-trimethylsilanylethynyl-non-1-en-4-ol | 140605-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-4-trimethylsilanylethynyl-non-1-en-4-ol
• 英文别名: 2-methyl-4-(2-trimethylsilylethynyl)non-1-en-4-ol
• CAS: 140605-56-7
• 化学式: C₁₅H₂₈OSi
• 分子量: 252.472
• InChiKey: YWFGZCRYEVWTLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-4-trimethylsilanylethynyl-non-1-en-4-ol 在 potassium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以100%的产率得到3-(2-methyl-1-propen)yl-1-octyn-3-ol
  参考文献：
  名称：

  Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo- and stereoselectivity.

  摘要：

  Radical cyclization of (bromomethyl)dimethylsilyl propargyl ether derivatives 1 is a powerful reaction with a high degree of regio-, chemo-, and stereoselectivity. Trisubstituted olefins 3, cyclopentene derivatives 5, and diquinane system 7j are obtained in good yields by a judicious choice of unsaturated substituents. Triquinane frameworks could be obtained stereoselectively from a suitable acyclic substrate of type 1 in a one-pot reaction. First attempts have not yet allowed us to aim at this goal due to interesting (1,5) hydrogen transfers. Moreover, we have intercepted, for the first time, the alpha-cyclopropyl radical which is involved in the Stork-Beckwith mechanism of the 5-versus 6-membered ring formation in the vinyl radical cyclization.

  DOI：

  10.1021/jo00037a026
• 作为产物：
  描述：

  1-(2-Methyl-2-propenoxy)-1-(trimethylsilyl)-1-octyne 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以100%的产率得到2-Methyl-4-trimethylsilanylethynyl-non-1-en-4-ol
  参考文献：
  名称：

  Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo- and stereoselectivity.

  摘要：

  Radical cyclization of (bromomethyl)dimethylsilyl propargyl ether derivatives 1 is a powerful reaction with a high degree of regio-, chemo-, and stereoselectivity. Trisubstituted olefins 3, cyclopentene derivatives 5, and diquinane system 7j are obtained in good yields by a judicious choice of unsaturated substituents. Triquinane frameworks could be obtained stereoselectively from a suitable acyclic substrate of type 1 in a one-pot reaction. First attempts have not yet allowed us to aim at this goal due to interesting (1,5) hydrogen transfers. Moreover, we have intercepted, for the first time, the alpha-cyclopropyl radical which is involved in the Stork-Beckwith mechanism of the 5-versus 6-membered ring formation in the vinyl radical cyclization.

  DOI：

  10.1021/jo00037a026