4-[1-(2,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-2,5-dimethoxy-1-(4-methyl-benzyl)-cyclohexa-2,5-dienecarbaldehyde | 192457-81-1

• 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: 4-[1-(2,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-2,5-dimethoxy-1-(4-methyl-benzyl)-cyclohexa-2,5-dienecarbaldehyde
• 英文别名: 4-[(2,5-dimethoxyphenyl)methylidene]-2,5-dimethoxy-1-[(4-methylphenyl)methyl]cyclohexa-2,5-diene-1-carbaldehyde
• CAS: 192457-81-1
• 化学式: C₂₆H₂₈O₅
• 分子量: 420.505
• InChiKey: FPEHGGYHCZAYQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[1-(2,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-2,5-dimethoxy-1-(4-methyl-benzyl)-cyclohexa-2,5-dienecarbaldehyde 反应 0.5h， 以67%的产率得到1,4-dimethoxy-2-(2,5-dimethoxybenzyl)-5-(4-methylbenzyl)benzene
  参考文献：
  名称：

  Phenyl−Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide

  摘要：

  By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl- carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.

  DOI：

  10.1021/jo9702498
• 作为产物：
  描述：

  在 氯化亚砜 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 4-[1-(2,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-2,5-dimethoxy-1-(4-methyl-benzyl)-cyclohexa-2,5-dienecarbaldehyde
  参考文献：
  名称：

  Phenyl−Carbonyl Coupling Reactions Promoted by Samarium Diiodide and Hexamethylphosphoramide

  摘要：

  By mediation of samarium diiodide and hexamethylphosphoramide, benzaldehydes and acetophenones underwent self- and cross-couplings to give the products having linkages at the para-carbons of phenyl rings and the carbonyl groups. The phenyl- carbonyl coupling of 2,5-dimethoxybenzaldehyde generated a Sm(III)-enolate intermediate, which was trapped by alkyl halides in a stereospecific manner to give uncommon 1,4-dialkyl-2,5-cyclohexadiene-1-carboxaldehydes. The benzaldehydes bearing tethered carbonyl chains proceeded with intramolecular phenyl-carbonyl couplings to afford fused benzocycles.

  DOI：

  10.1021/jo9702498