2-(3-bromophenyl)-4-oxo-4-phenylbutanal | 1437776-16-3

• 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: 2-(3-bromophenyl)-4-oxo-4-phenylbutanal
• 英文别名: 2-(3-Bromophenyl)-4-oxo-4-phenylbutanal
• CAS: 1437776-16-3
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: FTANLWLWBYOKLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(3-溴苯基)-1-苯基丙-2-烯-1-酮 、 D-阿拉伯糖 在 3,4,5-三甲基噻唑碘化物 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 130.0 ℃ 、413.69 kPa 条件下， 反应 0.17h， 以61%的产率得到2-(3-bromophenyl)-4-oxo-4-phenylbutanal
  参考文献：
  名称：

  Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones

  摘要：

  We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C-C bone cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.

  DOI：

  10.1021/ja401511r

文献信息

• Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones
  作者：Junmin Zhang、Chong Xing、Bhoopendra Tiwari、Yonggui Robin Chi

  DOI：10.1021/ja401511r

  日期：2013.6.5

  We disclose the first catalytic activation of carbohydrates as formaldehyde equivalents to generate acyl anions as one-carbon nucleophilic units for a Stetter reaction. The activation involves N-heterocyclic carbene (NHC)-catalyzed C-C bone cleavage of carbohydrates via a retro-benzoin-type process to generate the acyl anion intermediates. This Stetter reaction constitutes the first success in generating formal formaldehyde-derived acyl anions as one-carbon nucleophiles for non-self-benzoin processes. The renewable nature of carbohydrates, accessible from biomass, further highlights the practical potential of this fundamentally interesting catalytic activation.