trans-1-(2-vinylcyclohexyl)propan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-(2-vinylcyclohexyl)propan-1-one
• 英文别名: 1-(2-Ethenylcyclohexyl)propan-1-one；1-(2-ethenylcyclohexyl)propan-1-one
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: JHRQBZJERBURGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 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

• 作为反应物：
  描述：

  trans-1-(2-vinylcyclohexyl)propan-1-one 在 盐酸羟胺 、 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 27.5h， 生成 trans-(E)-diethyl 1-(2-vinylcyclohexyl)propylideneaminooxyphosphonate
  参考文献：
  名称：

  Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes

  摘要：

  Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 degrees C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a beta-aryl moiety possibly due to the stabilizing pi-pi stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.

  DOI：

  10.3987/com-11-12396
• 作为产物：
  描述：

  1-(2-乙烯基环己基)乙酮 在 正丁基锂 、 sodium methylate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 66.8h， 生成 trans-1-(2-vinylcyclohexyl)propan-1-one
  参考文献：
  名称：

  Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes

  摘要：

  Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 degrees C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a beta-aryl moiety possibly due to the stabilizing pi-pi stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.

  DOI：

  10.3987/com-11-12396

文献信息

• [EN] LOW MOLECULAR WEIGHT POLYGLUCOSAMINES AND POLYGALACTOSAMINES<br/>[FR] POLYGLUCOSAMINES ET DE POLYGALACTOSAMINES DE FAIBLE MASSE MOLECULAIRE
  申请人：DU PONT

  公开号：WO2007001282A2

  公开（公告）日：2007-01-04

  [EN] Compositions containing enriched populations of beta linked low molecular weight polymers of galactosamine and glucosamine are provided. The compositions are useful, for example, as antibacterial additives for food and other edible applications, as precursors for synthesizing other biologically active molecules related to chitin/chitosan oligomers, and/or as pharmaceutical compounds.
  [FR] L'invention concerne des compositions contenant des populations enrichies de polymères de faible masse moléculaire à liaison bêta de galactosamine et de glucosamine. Ces compositions conviennent, par exemple, en tant qu'additifs antibactériens pour des aliments et pour d'autres applications comestibles, en tant précurseurs pour la synthèse d'autres molécules bioactives liées aux oligomères chitine/chitosane et/ou en tant que composés pharmaceutiques.
• Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes
  作者：Jia-Liang Zhu、Sheng-Wei Tsao

  DOI：10.3987/com-11-12396

  日期：——

  Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 degrees C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a beta-aryl moiety possibly due to the stabilizing pi-pi stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.