imidazol-1-yl-pyren-1-yl-methanone | 197157-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: imidazol-1-yl-pyren-1-yl-methanone
• 英文别名: (1H-Imidazol-1-yl)(pyren-1-yl)methanone；imidazol-1-yl(pyren-1-yl)methanone
• CAS: 197157-66-7
• 化学式: C₂₀H₁₂N₂O
• 分子量: 296.328
• InChiKey: YVMCUYUULOOICD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  imidazol-1-yl-pyren-1-yl-methanone 、 (S)-4-((E)-(R)-13-Amino-1-hydroxy-tridec-2-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-4-{(E)-(R)-1-Hydroxy-13-[(pyrene-1-carbonyl)-amino]-tridec-2-enyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Fluorescence-labeled sphingosines as substrates of sphingosine kinases 1 and 2

  摘要：

  Fluorescently labeled D-erythro-sphingosines have been successfully synthesized in 9 and 12 steps starting from commercially available Garner aldehyde. Determining the influence of the nature, position and linkage of the label on the in vitro phosphorylation rate by sphingosine kinases 1 and 2 resulted in the identification of a pyrene- and a NBD-labeled sphingosine which are both phosphorylated with efficiency comparable to the natural substrate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.099

文献信息

• Energy-Transfer-Enabled Radical Acylation Using Free Alkyl Boronic Acids through Photo and NHC Dual Catalysis
  作者：Wan-Cong Liu、Xiang Zhang、Lin Chen、Rong Zeng、Yuan-Hang Tian、En-Dian Ma、Ya-Peng Wang、Bin Zhang、Jun-Long Li

  DOI：10.1021/acscatal.3c06027

  日期：2024.3.1

  for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they are rarely utilized as radical precursors for acylative coupling reactions. Herein, we reported an energy-transfer-enabled radical acylation using free alkyl boronic acids via NHC/photo dual catalysis. This protocol could efficiently

  交叉偶联反应作为最流行的酮合成方案之一而广受好评。作为重要的偶联伙伴，实验室稳定且市售的烷基硼酸广泛用于过渡金属催化，但很少用作酰化偶联反应的自由基前体。在此，我们报道了通过 NHC/光双催化使用游离烷基硼酸实现能量转移的自由基酰化。该方案可以有效促进烷基硼酸与酰基咪唑之间的铃木型交叉偶联以及烯烃的多组分烷基酰化，从而产生具有结构多样性的各种酮。此外，酮产品可以很容易地转化为大量结构有趣的精细化学品。初步机理研究揭示了独特的自由基反应机理。