3-methyl-3-(prop-1-enyl)cyclohexanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-3-(prop-1-enyl)cyclohexanone
• 英文别名: 3-Methyl-3-prop-1-enylcyclohexan-1-one
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: DWBLRWZEUJWCMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-3-(prop-1-enyl)cyclohexanone 、 溴化环丙基三苯鏻 在 sodium hydride 、 三(3,6-二氧杂庚基)胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.5h， 以32%的产率得到3-cyclopropylidene-1-methyl-1-(prop-1-enyl)cyclohexane
  参考文献：
  名称：

  Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes

  摘要：

  Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,S-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.

  DOI：

  10.1021/jo400139g
• 作为产物：
  描述：

  3-甲基-2-环己烯-1-酮 、 1-丙烯基溴化镁 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以71%的产率得到3-methyl-3-(prop-1-enyl)cyclohexanone
  参考文献：
  名称：

  Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes

  摘要：

  Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,S-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.

  DOI：

  10.1021/jo400139g

文献信息

• Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes
  作者：Ryan J. Felix、Osvaldo Gutierrez、Dean J. Tantillo、Michel R. Gagné

  DOI：10.1021/jo400139g

  日期：2013.6.7

  Gold(I) catalysts effectively promote the Cope rearrangement of acyclic 1,S-dienes bearing a terminal cyclopropylidene. When this methodology is applied to cyclic substrates an unexpected transformation occurs, resulting in the formation of a tricyclic compound incorporating a bicyclo[4.2.0]oct-1-ene core, a portion of which is found in a number of natural products. Density functional theory calculations (M06 and M06-2X) reveal insight into the mechanism and thermodynamics of this unique transformation.