(E)-2-(5,5,5-trifluoropent-3-en-1-yl)-1H-isoindole-1,3(2H)-dione | 1422056-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (E)-2-(5,5,5-trifluoropent-3-en-1-yl)-1H-isoindole-1,3(2H)-dione
• 英文别名: (E)-2-(5,5,5-trifluoropent-3-en-1-yl)isoindoline-1,3-dione；2-(5,5,5-trifluoropent-3-en-1-yl)isoindoline-1,3-dione
• CAS: 1422056-58-3
• 化学式: C₁₃H₁₀F₃NO₂
• 分子量: 269.223
• InChiKey: KASVMGYRZOPKGL-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-(3-bromo-5,5,5-trifluoropentyl)isoindoline-1,3-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到(E)-2-(5,5,5-trifluoropent-3-en-1-yl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  铜介导的未活化烯烃的卤代三氟甲基化

  摘要：

  开发了使用梅梅特试剂和卤化铜（I）（CuX，X = Cl，Br和I）的未激活的烯烃的铜介导的卤代三氟甲基化。选择CuX物种（CuI，CuBr和CuCl）作为铜和卤化物的来源，因为它们具有台式稳定性，商业可用性以及相对较低的成本。铜盐的简单交换提供了卤原子和CF 3基团同时和区域选择性地结合到各种烯烃上的期望效果。该方案为各种β-卤代三氟甲基化烷烃提供了一种有效而实用的途径。将CBr键进一步修饰为CB，CN和CS键。这些衍生化显示了后期修改的可行性。

  DOI：

  10.1002/adsc.201500731

文献信息

• Transition‐Metal‐Free Radical Hydrotrifluoromethylation of Alkynes
  作者：Kiran Matcha、Andrey P. Antonchick

  DOI：10.1002/ejoc.201800291

  日期：2019.1.23

  A combination of readily available and bench‐stable CF3SO2Na and tBuOOH was efficiently used for hydrotrifluoromethylation of alkynes. An excellent trans‐selectivity was demonstrated in the synthesis of alkenes. The developed mild reaction conditions allow the supression of the competing Meyer–Schuster‐type rearrangement.

  容易获得且稳定的CF 3 SO 2 Na和t BuOOH的组合有效地用于炔烃的加氢三氟甲基化。在烯烃的合成中表现出优异的反选择性。发达的温和反应条件可以抑制竞争性的Meyer–Schuster型重排。
• Catalytic Hydrotrifluoromethylation of Unactivated Alkenes
  作者：Satoshi Mizuta、Stefan Verhoog、Keary M. Engle、Tanatorn Khotavivattana、Miriam O’Duill、Katherine Wheelhouse、Gerasimos Rassias、Maurice Médebielle、Véronique Gouverneur

  DOI：10.1021/ja401022x

  日期：2013.2.20

  A visible-light-mediated hydrotrifluoromethylation of unactivated alkenes that uses the Umemoto reagent as the CF(3) source and MeOH as the reductant is disclosed. This effective transformation operates at room temperature in the presence of 5 mol % Ru(bpy)(3)Cl(2); the process is characterized by its operational simplicity and functional group tolerance.

  公开了使用 Umemoto 试剂作为 CF(3) 源和 MeOH 作为还原剂的未活化烯烃的可见光介导的氢三氟甲基化。这种有效的转变在室温下在 5 mol % Ru(bpy)(3)Cl(2) 存在下进行；该过程的特点是其操作简单和官能团耐受性。
• Metal-Free Photocatalytic Radical Trifluoromethylation Utilizing Methylene Blue and Visible Light Irradiation
  作者：Spencer P. Pitre、Christopher D. McTiernan、Hossein Ismaili、Juan C. Scaiano

  DOI：10.1021/cs5005823

  日期：2014.8.1

  The use of organofluorine compounds, especially those with an incorporated trifluoromethyl moiety, has increased dramatically in both the pharmaceutical and agrochemical industry. It has therefore become imperative to develop a mild and efficient synthetic technique for the inclusion of trifluoromethyl groups. Herein, we report the first use of methylene blue as a photosensitizer for the catalytic radical trifluoro- and hydrotrifluoromethylation of electron-rich heterocycles as well as terminal alkenes and alkynes under visible light irradiation. These reactions proceed with moderate to good yields at low catalyst concentrations; short irradiation times; and most importantly, without the need for potentially toxic transition-metal catalysts. In this work, considerable emphasis was also placed on understanding the kinetics of the mechanistically key steps through the use of laser flash photolysis techniques to more efficiently optimize the reaction conditions.