2-(1-phenylallyl)cyclohexanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1-phenylallyl)cyclohexanone
• 英文别名: (2S)-2-[(1S)-1-phenylprop-2-enyl]cyclohexan-1-one
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: NBOHSYPQDMVHPO-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-(1-phenylallyl)cyclohexanone 在 4-二甲氨基吡啶 、 L-Selectride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 反应 6.0h， 生成 [(1R,2R)-2-[(1R)-1-phenylprop-2-enyl]cyclohexyl] [(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonate
  参考文献：
  名称：

  Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines

  摘要：

  alpha-Carbanions of cyclic and acyclic imines have been successfully applied as nucleophiles in the Pd-catalyzed allylic alkylation reaction. Tuning of chemo- and regioselectivity has been realized by using t-BuOK/THF and LDA/toluene to give branched and linear products, respectively, with high regio- and diastereoselectivities. A plausible mechanism is proposed on the basis of the experimental results and DFT calculations.

  DOI：

  10.1021/ja2039503
• 作为产物：
  描述：

  肉桂基氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 、 异丙醇 为溶剂， 反应 3.5h， 生成 2-(1-phenylallyl)cyclohexanone 、 2-(1-phenylallyl)cyclohexanone
  参考文献：
  名称：

  Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines

  摘要：

  alpha-Carbanions of cyclic and acyclic imines have been successfully applied as nucleophiles in the Pd-catalyzed allylic alkylation reaction. Tuning of chemo- and regioselectivity has been realized by using t-BuOK/THF and LDA/toluene to give branched and linear products, respectively, with high regio- and diastereoselectivities. A plausible mechanism is proposed on the basis of the experimental results and DFT calculations.

  DOI：

  10.1021/ja2039503

文献信息

• The stereoselectivity of ketal Claisen rearrangements with ketals of simple cyclic ketones
  作者：G.William Daub、David A Griffith

  DOI：10.1016/s0040-4039(00)87795-3

  日期：1986.1

  Claisen rearrangements of the ketals of cyclopentanone, cyclohexanone and cycloheptanone give mixtures of and products favoring the isomer by as much as 19:1. The selectivity is attenuated by enolization processes in the 5- and 6-membered ring systems.

  环戊酮，环己酮和环庚酮的缩酮的克莱森重排给出了异构体的混合物和产物，它们的异构体比例高达19：1。在五元和六元环系统中，烯醇化过程会削弱选择性。
• Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines
  作者：Jian-Ping Chen、Qian Peng、Bai-Lin Lei、Xue-Long Hou、Yun-Dong Wu

  DOI：10.1021/ja2039503

  日期：2011.9.14

  alpha-Carbanions of cyclic and acyclic imines have been successfully applied as nucleophiles in the Pd-catalyzed allylic alkylation reaction. Tuning of chemo- and regioselectivity has been realized by using t-BuOK/THF and LDA/toluene to give branched and linear products, respectively, with high regio- and diastereoselectivities. A plausible mechanism is proposed on the basis of the experimental results and DFT calculations.