ethyl difluoro(4-hydroxyphenyl)acetate | 1394928-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl difluoro(4-hydroxyphenyl)acetate
• 英文别名: ethyl 2,2-difluoro-2-(4-hydroxyphenyl)acetate；Ethyl difluoro(4-hydroxyphenyl)acetate
• CAS: 1394928-30-3
• 化学式: C₁₀H₁₀F₂O₃
• 分子量: 216.184
• InChiKey: SCNCWIZDHYOHSB-UHFFFAOYSA-N

物化性质

• 沸点：
  302.2±37.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl difluoro(4-hydroxyphenyl)acetate 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 silver nitrate 、 Selectfluor 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 N-Boc氟西汀
  参考文献：
  名称：

  Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes

  摘要：

  Treatment of readily available alpha,alpha-difluoro- and alpha-fluoroarylacetic acids with Selecffluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [F-18]labeling is demonstrated using [F-18]Selectfluor bis(triflate), a reagent affording [F-18]tri- and [F-18]difluoromethylarenes not within reach with [F-18]F-2.

  DOI：

  10.1021/ol4009377
• 作为产物：
  描述：

  4-碘苯酚 、 二氟溴乙酸乙酯 在 铜 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以38%的产率得到ethyl difluoro(4-hydroxyphenyl)acetate
  参考文献：
  名称：

  Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes

  摘要：

  Treatment of readily available alpha,alpha-difluoro- and alpha-fluoroarylacetic acids with Selecffluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [F-18]labeling is demonstrated using [F-18]Selectfluor bis(triflate), a reagent affording [F-18]tri- and [F-18]difluoromethylarenes not within reach with [F-18]F-2.

  DOI：

  10.1021/ol4009377

文献信息

• Synthesis of α-Fluorinated Areneacetates through Photoredox/Copper Dual Catalysis
  作者：Guillaume Levitre、Albert Granados、María Jesús Cabrera-Afonso、Gary A. Molander

  DOI：10.1021/acs.orglett.2c00969

  日期：2022.5.6

  report a metallaphotoredox method for the preparation of fluoroalkyl arenes based on the synergistic combination of Ir/Cu dual catalysis from boronic acids. The mild conditions allow broad functional group tolerance, including substrates containing aldehydes, free phenols, and N-Boc-protected amines. Mechanistic investigations support a process proceeding via photoredox/copper dual catalysis.

  开发芳烃氟烷基化的温和且实用的条件是化学有机合成中持续存在的挑战。在此，我们报道了一种基于硼酸 Ir/Cu 双重催化协同组合的金属光氧化还原制备氟代烷基芳烃的方法。温和的条件允许广泛的官能团耐受性，包括含有醛、游离酚和N -Boc 保护的胺的底物。机理研究支持通过光氧化还原/铜双重催化进行的过程。
• Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes
  作者：Satoshi Mizuta、Ida S. R. Stenhagen、Miriam O’Duill、Jamie Wolstenhulme、Anna K. Kirjavainen、Sarita J. Forsback、Matthew Tredwell、Graham Sandford、Peter R. Moore、Mickael Huiban、Sajinder K. Luthra、Jan Passchier、Olof Solin、Véronique Gouverneur

  DOI：10.1021/ol4009377

  日期：2013.6.7

  Treatment of readily available alpha,alpha-difluoro- and alpha-fluoroarylacetic acids with Selecffluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stage fluorination strategy. Translation to [F-18]labeling is demonstrated using [F-18]Selectfluor bis(triflate), a reagent affording [F-18]tri- and [F-18]difluoromethylarenes not within reach with [F-18]F-2.