3-diphenylmethylsilyl-1-cyclohexenyl trimethylsilyl ether | 1025691-26-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-diphenylmethylsilyl-1-cyclohexenyl trimethylsilyl ether
• 英文别名: Trimethyl-[3-[methyl(diphenyl)silyl]cyclohexen-1-yl]oxysilane；trimethyl-[3-[methyl(diphenyl)silyl]cyclohexen-1-yl]oxysilane
• CAS: 1025691-26-2
• 化学式: C₂₂H₃₀OSi₂
• 分子量: 366.651
• InChiKey: ALXNLCHIBKBHND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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-diphenylmethylsilyl-1-cyclohexenyl trimethylsilyl ether 在 air 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以15%的产率得到3-methyldiphenylsilyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Silicon-Induced Ene-Type Reaction in the Thermal Conversion of Enolates to β-Silyl Enones with Molecular Dioxygen

  摘要：

  Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with molecular dioxygen in toluene at 110 degrees C produced the corresponding conjugated enones in yields up to 88% yield. The reaction of the same type failed on replacement of the silyl group at the C-3 position with an isopropyl group. These results indicate the existence of an unprecedented silicon-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed.

  DOI：

  10.1021/ol800007v
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-环己烯-1-酮 、 甲基二苯基氯硅烷 在 lithium 、 氰化亚铜 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以80%的产率得到3-diphenylmethylsilyl-1-cyclohexenyl trimethylsilyl ether
  参考文献：
  名称：

  Silicon-Induced Ene-Type Reaction in the Thermal Conversion of Enolates to β-Silyl Enones with Molecular Dioxygen

  摘要：

  Reaction of alkyl, acetoxy, and silyl enol ethers of 3-(organosilyl)cyclohexanone with molecular dioxygen in toluene at 110 degrees C produced the corresponding conjugated enones in yields up to 88% yield. The reaction of the same type failed on replacement of the silyl group at the C-3 position with an isopropyl group. These results indicate the existence of an unprecedented silicon-induced ene-type reaction. Its reaction mechanism, generality, limitations, and exceptions are discussed.

  DOI：

  10.1021/ol800007v