2-(4-methoxyphenyl)-2-(naphthalen-2-yl)-1-phenylethanone | 1218936-98-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-methoxyphenyl)-2-(naphthalen-2-yl)-1-phenylethanone
• CAS: 1218936-98-1
• 化学式: C₂₅H₂₀O₂
• 分子量: 352.433
• InChiKey: OGLKLEWMQLSQHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-(naphthalen-2-yl)-1-phenyl-2-(phenylselanyl)ethan-1-ol 在 肉桂酸 、 rose bengal 作用下， 19.0~23.0 ℃ 、101.33 kPa 条件下， 以72 %的产率得到2-(4-methoxyphenyl)-2-(naphthalen-2-yl)-1-phenylethanone
  参考文献：
  名称：

  Hydrogen‐Bond‐Modulated Nucleofugality of Se ^III Species to Enable Photoredox‐Catalytic Semipinacol Manifolds

  摘要：

  AbstractChemical bond activations mediated by H‐bond interactions involving highly electronegative elements such as nitrogen and oxygen are powerful tactics in modern catalysis research. On the contrary, kindred catalytic regimes in which heavier, less electronegative elements such as selenium engage in H‐bond interactions to co‐activate C−Se σ‐bonds under oxidative conditions are elusive. Traditional strategies to enhance the nucleofugality of selenium residues predicate on the oxidative addition of electrophiles onto SeII‐centers, which entails the elimination of the resulting SeIV moieties. Catalytic procedures in which SeIV nucleofuges are substituted rather than eliminated are very rare and, so far, not applicable to carbon‐carbon bond formations. In this study, we introduce an unprecedented combination of O−H⋅⋅⋅Se H‐bond interactions and single electron oxidation to catalytically generate SeIII nucleofuges that allow for the formation of new C−C σ‐bonds by means of a type I semipinacol process in high yields and excellent selectivity.

  DOI：

  10.1002/anie.202208611

文献信息

• Lewis Acid-Promoted Friedel−Crafts Alkylation Reactions with α-Ketophosphate Electrophiles
  作者：Austin G. Smith、Jeffrey S. Johnson

  DOI：10.1021/ol100410k

  日期：2010.4.16

  The BF3·OEt2-promoted nucleophilic substitution of α-aryl-α-ketophosphates to afford α,α-diaryl ketone products is described. Electron-rich α-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic, and nonaromatic nucleophiles, with yields ranging from 44% to 84%. Enantioenriched starting material

  描述了BF 3 ·OEt 2促进的α-芳基-α-酮磷酸盐的亲核取代，以提供α，α-二芳基酮产物。富含电子的α-酮磷酸酯的性能最佳，同时还可以耐受电子中性和贫电子的底物。该反应可耐受多种芳族，杂芳族和非芳族亲核试剂，收率范围为44％至84％。富含对映体的原料产生外消旋产物，表明通过酰基carb离子的S N 1途径。