trans-2-vinylcyclohexanecarbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: trans-2-vinylcyclohexanecarbaldehyde
• 英文别名: 2-Ethenylcyclohexane-1-carbaldehyde
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: KXRGCMHBLSLIKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-2-vinylcyclohexanecarbaldehyde 在 盐酸羟胺 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以398 mg的产率得到
  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：

  2-vinylcyclohexanecarbaldehyde 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以870 mg的产率得到trans-2-vinylcyclohexanecarbaldehyde
  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.
• [EN] CHEMICAL SYNTHESIS OF LOW MOLECULAR WEIGHT POLYGLUCOSAMINES AND POLYGALACTOSAMINES<br/>[FR] SYNTHESE CHIMIQUE DE POLYGLUCOSAMINES ET DE POLYGALACTOSAMINES DE FAIBLE MASSE MOLECULAIRE
  申请人：DU PONT

  公开号：WO2007001283A2

  公开（公告）日：2007-01-04

  [EN] A process for the synthesis of beta linked low molecular weight polymers of galactosamine and glucosamine has been developed. Through the use of high amounts of activating agents, efficient coupling of stable monomers is achieved. Using this process, chain extension is through the addition of single monomers, providing populations of single chain length polyhexosamines.
  [FR] L'invention concerne un procédé de synthèse de polymères de faible masse moléculaire à liaison bêta de galactosamine et de glucosamine. Un couplage efficace de monomères stables est obtenu au moyen de taux élevés d'agents activants. Dans ce procédé, l'allongement de chaîne se fait par l'addition de monomères uniques, de façon à produire des populations de polyhexosamines à une seule longueur de chaîne.
• 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.