3-(2-Methyl-2-propenyl)-1,7-bis(trimethylsilyl)-1,6-heptadiyn-3-ol | 140605-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Methyl-2-propenyl)-1,7-bis(trimethylsilyl)-1,6-heptadiyn-3-ol
• 英文别名: 2-methyl-8-trimethylsilyl-4-(2-trimethylsilylethynyl)oct-1-en-7-yn-4-ol
• CAS: 140605-62-5
• 化学式: C₁₇H₃₀OSi₂
• 分子量: 306.596
• InChiKey: IJONOJAZUZVYKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(2-Methyl-2-propenyl)-1,7-bis(trimethylsilyl)-1,6-heptadiyn-3-ol 在 4-二甲氨基吡啶 、 potassium fluoride 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.25h， 生成 4-<(Bromomethyl)dimethylsilyloxy>-4-ethynyl-2-methyl-1-octen-7-yne
  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：

  5-(三甲基硅烷基)-4-戊炔-1-醇 在 六甲基磷酰三胺 、 正丁基锂 、 1,10-菲罗啉 、 乙基溴化镁 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 3-(2-Methyl-2-propenyl)-1,7-bis(trimethylsilyl)-1,6-heptadiyn-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