2-cyclohexyl-4,6-diphenyl-4H-pyran-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-cyclohexyl-4,6-diphenyl-4H-pyran-3-carbaldehyde
• 英文别名: mdk-3-148；mdk-4-110
• 化学式: C₂₄H₂₄O₂
• 分子量: 344.453
• InChiKey: SGAKJOVIQZLPES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyclohexyl-4,6-diphenyl-4H-pyran-3-carbaldehyde 、 2,4-二硝基苯肼 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以92%的产率得到mdk-3-058
  参考文献：
  名称：

  N-Heterocyclic Carbene-Promoted Annulation Reaction of Allenals with Chalcones: Synthesis of Polysubstituted Pyranyl Aldehydes

  摘要：

  A general N-heterocyclic carbene (NHC)-promoted annulation reaction of allenals with chalcones affording polysubstituted pyranyl aldehydes has been developed. Three mechanistic possible pathways have been proposed. The NHC attacks the center carbon of allenals or acts as a base for deprotonation and then undergoes a 1,4-addition with chalcones, followed by sequential reactions giving the final products.

  DOI：

  10.1021/ol5021509
• 作为产物：
  描述：

  3-环己基亚基丙烯醛 、 苯亚甲基苯乙酮 在 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 以84%的产率得到2-cyclohexyl-4,6-diphenyl-4H-pyran-3-carbaldehyde
  参考文献：
  名称：

  N-Heterocyclic Carbene-Promoted Annulation Reaction of Allenals with Chalcones: Synthesis of Polysubstituted Pyranyl Aldehydes

  摘要：

  A general N-heterocyclic carbene (NHC)-promoted annulation reaction of allenals with chalcones affording polysubstituted pyranyl aldehydes has been developed. Three mechanistic possible pathways have been proposed. The NHC attacks the center carbon of allenals or acts as a base for deprotonation and then undergoes a 1,4-addition with chalcones, followed by sequential reactions giving the final products.

  DOI：

  10.1021/ol5021509

文献信息

• <i>N</i>-Heterocyclic Carbene-Promoted Annulation Reaction of Allenals with Chalcones: Synthesis of Polysubstituted Pyranyl Aldehydes
  作者：Dengke Ma、Youai Qiu、Jianxin Dai、Chunling Fu、Shengming Ma

  DOI：10.1021/ol5021509

  日期：2014.9.19

  A general N-heterocyclic carbene (NHC)-promoted annulation reaction of allenals with chalcones affording polysubstituted pyranyl aldehydes has been developed. Three mechanistic possible pathways have been proposed. The NHC attacks the center carbon of allenals or acts as a base for deprotonation and then undergoes a 1,4-addition with chalcones, followed by sequential reactions giving the final products.