(E)-2-(2-(2-methyl-3-oxo-3-phenylprop-1-enyl)phenoxy)acetaldehyde | 1093957-61-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-(2-(2-methyl-3-oxo-3-phenylprop-1-enyl)phenoxy)acetaldehyde
• CAS: 1093957-61-9
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: OMBSWZXLHZFOMJ-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(2-methyl-3-oxo-3-phenylprop-1-enyl)phenoxy)acetaldehyde 在 N₂-mesityl-N₄-methyl-5-methyltriazolium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以70%的产率得到4-(1-oxo-1-phenylpropan-2-yl)chroman-2-one
  参考文献：
  名称：

  NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins

  摘要：

  N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4 through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst Is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.

  DOI：

  10.1021/ol802448c
• 作为产物：
  描述：

  在 Amberlyst 15 resin 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 (E)-2-(2-(2-methyl-3-oxo-3-phenylprop-1-enyl)phenoxy)acetaldehyde
  参考文献：
  名称：

  NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins

  摘要：

  N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4 through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst Is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.

  DOI：

  10.1021/ol802448c