(E)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetaldehyde | 1093957-66-4

• 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-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy)acetaldehyde
• 英文别名: (E)-2-(2-(3-oxo-3-phenylprop-1-enyl)phenoxy)acetaldehyde；2-[2-[(E)-3-oxo-3-phenylprop-1-enyl]phenoxy]acetaldehyde
• CAS: 1093957-66-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: UGICXKAUMGRSHI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)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 3.0h， 以83%的产率得到4-(2-oxo-2-phenylethyl)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， 以81%的产率得到(E)-2-(2-(3-oxo-3-phenylprop-1-en-1-yl)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

文献信息

• NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins
  作者：Eric M. Phillips、Manabu Wadamoto、Howard S. Roth、Andrew W. Ott、Karl A. Scheidt

  DOI：10.1021/ol802448c

  日期：2009.1.1

  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.
• Enantioselective Formation of Substituted 3,4-Dihydrocoumarins by a Multicatalytic One-Pot Process
  作者：Christian Borch Jacobsen、Łukasz Albrecht、Jonas Udmark、Karl Anker Jørgensen

  DOI：10.1021/ol302627u

  日期：2012.11.2

  The formation of optically active 3,4-dihydrocoumarins is presented by merging aminocatalysis with an N-heterocyclic carbene-catalyzed internal redox reaction. The products are formed in good to excellent yields and in general with excellent enantioselectivities. Moreover, the developed procedure demonstrates the potential of enantioselective, multicatalytic sequences. By employing an enantiopure aminocatalyst in the enantiodifferentiating step, the challenges related to achieving high stereoinductions by deployment of optically active NHC-catalysts can be circumvented.