2-((E)-Prop-1-en-1-yl)-1-acetylcyclohexene | 132079-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((E)-Prop-1-en-1-yl)-1-acetylcyclohexene
• 英文别名: 1-[2-[(E)-prop-1-enyl]cyclohexen-1-yl]ethanone
• CAS: 132079-94-8
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: DAWCVUTUZOMWRO-ZZXKWVIFSA-N

物化性质

• 沸点：
  267.6±19.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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-乙酰基环己酮 在 四(三苯基膦)钯 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 48.0h， 生成 2-((E)-Prop-1-en-1-yl)-1-acetylcyclohexene
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling of .beta.-(methanesulfonyl)oxyenones with organostannanes

  摘要：

  beta-(Methanesulfonyl)oxy enones, derived from 1,3-diones, cross-couple with vinylstannanes in 50-80% yields when a substoichiometric amount of Pd(PPh3)4 and stoichiometric lithium bromide are used. Phenyltributylstannane affords low yields of cross-coupled product. Tetrabutyltin, tributyltin hydride, and ethynyltributyltin do not couple under the reaction conditions. The reaction is proposed to involve in situ formation of the beta-bromo enone, oxidative addition to the Pd(0) catalyst, transmetalation, and reductive elimination to afford cross-coupled products. The analogous enol phosphates undergo coupling in low yields, the major product resulting from regeneration of the 1,3-dione.

  DOI：

  10.1021/jo00004a028

文献信息

• Palladium-catalyzed cross-coupling of .beta.-(methanesulfonyl)oxyenones with organostannanes
  作者：Christina M. Hettrick、James K. Kling、William J. Scott

  DOI：10.1021/jo00004a028

  日期：1991.2

  beta-(Methanesulfonyl)oxy enones, derived from 1,3-diones, cross-couple with vinylstannanes in 50-80% yields when a substoichiometric amount of Pd(PPh3)4 and stoichiometric lithium bromide are used. Phenyltributylstannane affords low yields of cross-coupled product. Tetrabutyltin, tributyltin hydride, and ethynyltributyltin do not couple under the reaction conditions. The reaction is proposed to involve in situ formation of the beta-bromo enone, oxidative addition to the Pd(0) catalyst, transmetalation, and reductive elimination to afford cross-coupled products. The analogous enol phosphates undergo coupling in low yields, the major product resulting from regeneration of the 1,3-dione.