(E)-3-ethylidene-7-(trifluoromethyl)chroman-4-one | 1610423-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-ethylidene-7-(trifluoromethyl)chroman-4-one
• 英文别名: (3E)-3-ethylidene-7-(trifluoromethyl)chromen-4-one
• CAS: 1610423-81-8
• 化学式: C₁₂H₉F₃O₂
• 分子量: 242.197
• InChiKey: FUWXAFQGHCKEQB-FARCUNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-2-((4-bromobut-2-en-1-yl)oxy)-4-(trifluoromethyl)benzaldehyde 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以76%的产率得到(E)-3-ethylidene-7-(trifluoromethyl)chroman-4-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Intramolecular Acylation of Allylic Electrophiles

  摘要：

  The N-heterocyclic carbene (NHC) catalyzed addition reaction has been well documented recently; however, the NHC-catalyzed substitution reaction especially the S(N)2' type reaction remains a challenge. As one of the most fundamental reaction types in organic chemistry, the S(N)2' reaction catalyzed by NHC would be a powerful tool in organic synthesis. Therefore, the first NHC-catalyzed intramolecular S(N)2' substitution reaction of aldehyde with allylic electrophiles has been developed. A variety of alpha,beta-unsaturated chromanones were obtained under a domino S(N)2' reaction and isomerization. Mechanistic experiments were conducted to confirm the nature of this S(N)2' reaction.

  DOI：

  10.1021/ol501046p