4-methyl-2-oxo-3-(trifluoromethyl)-2H-chromen-7-yl acetate | 1562426-88-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methyl-2-oxo-3-(trifluoromethyl)-2H-chromen-7-yl acetate
• 英文别名: 7-acetyloxy-4-methyl-3-(trifluoromethyl)-2H-1-benzopyran-2-one；[4-Methyl-2-oxo-3-(trifluoromethyl)chromen-7-yl] acetate
• CAS: 1562426-88-3
• 化学式: C₁₃H₉F₃O₄
• 分子量: 286.207
• InChiKey: GSMHXMWQQVLSPE-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  331.5±42.0 °C(predicted)
• 密度：
  1.404±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-苯二醇单乙酸酯 在 硫酸 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 24.25h， 生成 4-methyl-2-oxo-3-(trifluoromethyl)-2H-chromen-7-yl acetate
  参考文献：
  名称：

  锰（III）介导的香豆素与三氟甲亚磺酸钠的直接Csp2-H自由基三氟甲基化。

  摘要：

  描述了用CF3SO2Na（Langlois试剂）对香豆素进行Mn（OAc）3介导的Csp2-H自由基三氟甲基化，以中等至良好的产率提供选择性的3-三氟甲基香豆素。该方法也可以应用于喹啉酮和嘧啶酮的三氟甲基化。

  DOI：

  10.1039/c3cc49689a

文献信息

• Catalyst-free electrochemical trifluoromethylation of coumarins using CF₃SO₂NHNHBoc as the CF₃ source
  作者：Nannan Cen、Han Wang、YiCheng Zhou、Ruoqu Gong、Dandan Sui、Wenbo Chen

  DOI：10.1039/d2ob01925f

  日期：——

  An efficient electrochemical trifluoromethylation of coumarins using CF₃SO₂NHNHBoc as the source of the trifluoromethyl group was developed.

  使用CF₃SO₂NHNHBoc作为三氟甲基基团的来源，开发了一种高效的香豆素的电化学三氟甲基化反应。
• Scalable decarboxylative trifluoromethylation by ion-shielding heterogeneous photoelectrocatalysis
  作者：Yixin Chen、Yuchen He、Yong Gao、Jiakun Xue、Wei Qu、Jun Xuan、Yiming Mo

  DOI：10.1126/science.adm8902

  日期：2024.5.10

  Electrochemistry offers a sustainable synthesis route to value-added fine chemicals but is often constrained by competing electron transfer between the electrode and redox-sensitive functionalities distinct from the target site. Here, we describe an ion-shielding heterogeneous photoelectrocatalysis strategy to impose mass-transfer limitations that invert the thermodynamically determined order of electron transfer. This strategy is showcased to enable decarboxylative trifluoromethylation of sensitive (hetero)arenes by using trifluoroacetate, an inexpensive yet relatively inert trifluoromethyl group (CF 3 ) source. An ion-shielding layer, formed by trifluoroacetate anions electrostatically adsorbed on a positive molybdenum-doped tungsten trioxide (WO 3 ) photoanode, prevents undesired electron transfer between substrates and photogenerated holes. The practicality of the developed method was demonstrated with robust photoanode stability (approximately 380 hours), a good substrate scope, and scaling capability to achieve 100-gram synthesis by using photoelectrochemical flow cells.