3-<(E)-4-Iodo-2-methyl-1-butenyl>cyclohexanone | 140926-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<(E)-4-Iodo-2-methyl-1-butenyl>cyclohexanone
• 英文别名: 3-[(E)-4-iodo-2-methylbut-1-enyl]cyclohexan-1-one
• CAS: 140926-64-3
• 化学式: C₁₁H₁₇IO
• 分子量: 292.16
• InChiKey: WAGFONAZVHHQOF-VQHVLOKHSA-N

物化性质

• 沸点：
  322.6±35.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 4-碘-1-丁炔 、 三甲基铝 生成 3-<(E)-4-Iodo-2-methyl-1-butenyl>cyclohexanone
  参考文献：
  名称：

  Transmetalation reactions of alkenylalanes: copper-catalyzed conjugate addition to enones

  摘要：

  An improved synthetic strategy for the in situ preparation of vinyl cuprates from alkynes is presented and used for the stereospecific synthesis of di-, tri-, and tetrasubstituted olefin& Hydroalumination or Cp2ZrCl2-catalyzed carboalumination of alkynes, followed by in situ transmetalation to bis-alkynyl-copper complex [(C4H9C = C)2CuCN]Li2 and addition of enones, led to the isolation of 1,4-addition products in high yields. Stoichiometric or catalytic amounts of copper complex gave similar results. However, in the presence of less than 10 mol % of Cu(I) complex, side products were formed and a significant drop in the yield of the desired conjugate addition product was observed. An ate-transfer mechanism is postulated for the rapid exchange of vinyl ligands from AI(III) to Cu(I) at low temperatures.

  DOI：

  10.1021/jo00037a040

文献信息

• Transmetalation reactions of alkenylalanes: copper-catalyzed conjugate addition to enones
  作者：Peter Wipf、Jacqueline H. Smitrovich、Choong Woon Moon

  DOI：10.1021/jo00037a040

  日期：1992.5

  An improved synthetic strategy for the in situ preparation of vinyl cuprates from alkynes is presented and used for the stereospecific synthesis of di-, tri-, and tetrasubstituted olefin& Hydroalumination or Cp2ZrCl2-catalyzed carboalumination of alkynes, followed by in situ transmetalation to bis-alkynyl-copper complex [(C4H9C = C)2CuCN]Li2 and addition of enones, led to the isolation of 1,4-addition products in high yields. Stoichiometric or catalytic amounts of copper complex gave similar results. However, in the presence of less than 10 mol % of Cu(I) complex, side products were formed and a significant drop in the yield of the desired conjugate addition product was observed. An ate-transfer mechanism is postulated for the rapid exchange of vinyl ligands from AI(III) to Cu(I) at low temperatures.