2-bromobenzyl 2-fluorobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromobenzyl 2-fluorobenzoate
• 英文别名: (2-Bromophenyl)methyl 2-fluorobenzoate
• 化学式: C₁₄H₁₀BrFO₂
• mdl: MFCD25563473
• 分子量: 309.135
• InChiKey: QCGXWWCXLQBODC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromobenzaldehyde hydrazone 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 氘代氯仿 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 生成 2-bromobenzyl 2-fluorobenzoate
  参考文献：
  名称：

  An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion

  摘要：

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.

  DOI：

  10.1021/ol200402m

文献信息

• Titration of Nonstabilized Diazoalkane Solutions by Fluorine NMR
  作者：Victor L. Rendina、Jason S. Kingsbury

  DOI：10.1021/jo202214e

  日期：2012.1.20

  A new protocol for titrating nonstabilized diazoalkane solutions by quantitative 19F NMR is reported. An excess of 2-fluorobenzoic acid dissolved in CDCl3 is treated with the diazoalkane solution at a low temperature, immediately forming the corresponding 2-fluorobenzoate ester upon warming. A significant difference in the 19F chemical shift between the ester and acid is seen, allowing facile and accurate

  报道了通过定量19 F NMR滴定不稳定的重氮烷溶液的新方案。用重氮烷溶液在低温下处理溶解在CDCl 3中的过量的2-氟苯甲酸，在加热后立即形成相应的2-氟苯甲酸酯。观察到酯和酸之间在19 F化学位移方面存在显着差异，从而可以轻松，准确地积分来确定滴度。该过程安全，快速，并且可以高精度指示活性重氮烷浓度。
• An Enantioselective Synthesis of 2-Aryl Cycloalkanones by Sc-Catalyzed Carbon Insertion
  作者：Victor L. Rendina、David C. Moebius、Jason S. Kingsbury

  DOI：10.1021/ol200402m

  日期：2011.4.15

  Current methods for asymmetric alpha-arylation require blocking groups to prevent reaction at the alpha'-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.