5-(trifluoromethyl)benzo[d][1,3]dioxole | 1254164-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(trifluoromethyl)benzo[d][1,3]dioxole
• 英文别名: 5-(Trifluoromethyl)-1,3-benzodioxole；5-(trifluoromethyl)-1,3-benzodioxole
• CAS: 1254164-46-9
• 化学式: C₈H₅F₃O₂
• 分子量: 190.122
• InChiKey: KPBAALQWUKRVRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-[2-(methylthio)-1,3-dithian-2-yl]benzo[d][1,3]dioxole 在 iodine pentafluoride-pyridine-hydrogen fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以60%的产率得到5-(trifluoromethyl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  IF5–pyridine–HF: air- and moisture-stable fluorination reagent

  摘要：

  IF5-pyridine-HF, an air- and moisture-stable solid, can be used as a fluorination reagent for the introduction of fluorine atoms to the alpha-position of the sulfur atom in sulfides. The desulfurizing-fluorination reactions of benzylic sulfides, thioacetals, and 2-(methylthio)-1,3-dithiane derivatives were also performed using this reagent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.104

文献信息

• Cross‐Coupling through Ag(I)/Ag(III) Redox Manifold
  作者：Luca Demonti、Nathalie Saffon‐Merceron、Nicolas Mézailles、Noel Nebra

  DOI：10.1002/chem.202102836

  日期：2021.11.5

  trifluoromethylation via AgI/AgIII redox shuttles are herein deciphered. This innovative cross-coupling, analogous to the CEL coupling popularized by copper, involves: i) easy AgI/AgIII 2e− oxidation; ii) phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) benzotrifluoride production from aryl-AgIII intermediates. Now, AgIIICF3 chemistry is safe and reachable from AgF, KF, CF3TMS and air.

  教银做伎俩。通过Ag I / Ag III氧化还原穿梭进行氧化三氟甲基化的最关键步骤在本文中被破译。这种创新的交叉耦合类似于铜普及的 CEL 耦合，包括：i)容易的 Ag I /Ag III 2 e -氧化；ii)苯连接到 Ag III 上；iii)硼到 Ag III芳基转移；和ⅳ）三氟甲苯产量从芳基的Ag III中间体。现在，Ag III CF 3化学是安全的，可以从 AgF、KF、CF 3 TMS 和空气中获得。
• Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids
  作者：Lingling Chu、Feng-Ling Qing

  DOI：10.1021/ol1023135

  日期：2010.11.5

  A copper-mediated oxidative cross-coupling of aryl- and alkenylboronic acids with (trifluoromethyl)trimethylsilane (Me3SiCF3) under mild conditions has been developed. This method allows a wide range of functional group tolerant trifluoromethylated arenes and alkenes to be easily prepared. This oxidative trifluoromethylation has the potential to introduce trifluoromethyl groups into advanced, highly

  已经开发了在温和条件下铜介导的芳基和烯基硼酸与（三氟甲基）三甲基硅烷（Me 3 SiCF 3）的氧化交叉偶联。该方法允许容易地制备宽范围的耐官能团的三氟甲基化的芳烃和烯烃。这种氧化三氟甲基化有可能将三氟甲基引入先进的，高度官能化的有机分子中。
• Transition-metal-free oxidative trifluoromethylation of unsymmetrical biaryls with trifluoromethanesulfinate
  作者：Yu-Dong Yang、Kanji Iwamoto、Etsuko Tokunaga、Norio Shibata

  DOI：10.1039/c3cc41667d

  日期：——

  A transition-metal-free direct oxidative trifluoromethylation of unsymmetrical biaryls has been achieved by the simple combination of trifluoromethanesulfinate and phenyliodine bis(trifluoroacetate). The trifluoromethylation is selectively observed in the electron-rich arenes.

  实现了一种无过渡金属的直接氧化三氟甲基化不对称联苯的方法，采用了三氟甲基磺酸盐和二（三氟乙酸）碘苯的简单组合。三氟甲基化在富电子芳烃中具有选择性。
• Oxidative Trifluoromethylation of Arylboronates with Shelf-Stable Potassium (Trifluoromethyl)trimethoxyborate
  作者：Bilal A. Khan、Annette E. Buba、Lukas J. Gooßen

  DOI：10.1002/chem.201102652

  日期：2012.2.6

  Introducing CF3: Arylboronic acid pinacol esters are converted into the corresponding benzotrifluorides with the easy‐to‐use one‐component trifluoromethylating reagent potassium (trifluoromethyl)trimethoxyborate, mediated by copper acetate under an oxygen atmosphere (see scheme).

  引入CF 3：芳氧硼酸频哪醇酯与易用的单组分三氟甲基化试剂（三氟甲基）三甲氧基硼酸钾在氧气气氛下通过乙酸铜转化为相应的苯并三氟化物（参见方案）。
• Copper-catalyzed trifluoromethylation of aryl- and vinylboronic acids with generation of CF3-radicals
  作者：Yang Li、Lipeng Wu、Helfried Neumann、Matthias Beller

  DOI：10.1039/c2cc36554e

  日期：——

  The selective trifluoromethylation of aryl- and vinylboronic acids proceeds smoothly with CF3SO2Na (Langlois reagent) in the presence of copper catalysts and t-BuOOH. Therefore, the method relies both on transition metal catalysis and selective radical reactions. Advantageously, the protocol can be performed at room temperature under an air atmosphere and avoids the issue of poor regioselectivity.

  在铜催化剂和 t-BuOOH 的存在下，CF3SO2Na（朗格卢瓦试剂）可顺利进行芳基和乙烯基硼酸的选择性三氟甲基化反应。因此，该方法既依赖于过渡金属催化，又依赖于选择性自由基反应。更有利的是，该方法可在室温和空气环境下进行，避免了区域选择性差的问题。