6-methyl-4-(4-(trifluoromethyl)phenyl)-2H-pyran-2-one | 1334224-68-8

• 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: 6-methyl-4-(4-(trifluoromethyl)phenyl)-2H-pyran-2-one
• 英文别名: 4-(4-trifluoromethylphenyl)-6-methyl-2-pyranone；6-methyl-4-(4-(trifluoromethyl)phenyl)-2-pyrone；6-methyl-4-[4-(trifluoromethoxy)phenyl]-2(2H)-pyranone；6-Methyl-4-[4-(trifluoromethyl)phenyl]pyran-2-one；6-methyl-4-[4-(trifluoromethyl)phenyl]pyran-2-one
• CAS: 1334224-68-8
• 化学式: C₁₃H₉F₃O₂
• 分子量: 254.208
• InChiKey: JYMHGFNKHOJXSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methyl-4-(4-(trifluoromethyl)phenyl)-2H-pyran-2-one 在 4-二甲氨基吡啶 、 selenium 、 三氯硅烷 作用下， 反应 6.0h， 以63%的产率得到6-methyl-4-(4-(trifluoromethyl)phenyl)-2H-pyran-2-selone
  参考文献：
  名称：

  2-吡喃酮和香豆素的第一个硒异构体：合成、结构和反应

  摘要：

  2-吡喃酮和香豆素与氢氯硅烷、元素硒和 4-二甲氨基吡啶 (DMAP) 的反应以中等至良好的产率得到 2-硒吡喃酮和硒香豆素。他们的...

  DOI：

  10.1246/cl.170341
• 作为产物：
  描述：

  5-iodo-5-methyl-3-(4-(trifluoromethyl)phenyl)cyclopent-2-en-1-one 在 air 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以54%的产率得到6-methyl-4-(4-(trifluoromethyl)phenyl)-2H-pyran-2-one
  参考文献：
  名称：

  α-碘代环戊烯酮无催化剂和无添加剂的Baeyer-Villiger型氧化为α-吡喃酮：使用空气作为氧化剂†

  摘要：

  描述了一种有效的合成方法，该方法通过使用空气作为环境良性氧化剂的无催化剂和无添加剂系统，通过α-碘代环戊烯的Baeyer-Villiger型氧化来合成α-吡喃酮。该反应显示出优异的官能团相容性，并为在温和的反应条件下构建高度官能化的α-吡喃酮提供了简单有效的方案。

  DOI：

  10.1039/c9gc02725d

文献信息

• An Economical Access to 3,4-Diaryl-2(5<i>H</i>)-furanones and 4-Aryl-6-methyl-2(2<i>H</i>)-pyranones by Pd-Catalyzed Suzuki-Type Arylation of 3-Aryl-4-tosyloxy-2(5<i>H</i>)-furanones and 6-Methyl-4-tosyloxy-2(2<i>H</i>)-pyranones, Respectively
  作者：Fabio Bellina、Chiara Marchetti、Renzo Rossi

  DOI：10.1002/ejoc.200900581

  日期：2009.9

  4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosyloxy-2(5H)-furanones as the key step. The mild conditions of this arylation protocol have also been used for the high yielding synthesis of 4-aryl-6-methyl-2(2H)-pyranones from 6-methyl-4-tosyloxy-2(2H)-pyranone. (© Wiley-VCH

  对称和非对称 3,4-二芳基取代的 2(5H)-呋喃酮均已使用廉价的方法高效合成，该方法涉及 Pd(OAc)2/PCy3 催化的 Suzuki 型芳基化容易获得的 3-芳基-4-甲苯磺酰氧基-2(5H)-呋喃酮是关键步骤。该芳基化方案的温和条件也已用于从 6-甲基-4-甲苯磺酰氧基-2(2H)-吡喃酮高产合成 4-芳基-6-甲基-2(2H)-吡喃酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Multisubstituted naphthalene synthesis from 4-hydroxy-2-pyrones through [4+2] cycloaddition with <i>o</i>-silylaryl triflates
  作者：Koyo Numata、Shinya Tabata、Akihiro Kobayashi、Suguru Yoshida

  DOI：10.1039/d3nj03831a

  日期：——

  for multisubstituted naphthalenes from 4-hydroxy-2-pyrones through cycloaddition with aryne intermediates is disclosed. Various highly functionalized 2-pyrones were synthesized through 4-hydroxy-2-pyrones in short steps. The resulting 2-pyrones reacted smoothly with a wide range of aryne intermediates generated from o-silylaryl triflates to provide multisubstituted naphthalenes by the Diels–Alder reaction

  公开了一种通过与芳炔中间体环加成从4-羟基-2-吡喃酮有效合成多取代萘的方法。通过4-羟基-2-吡喃酮在短时间内合成了各种高功能化的2-吡喃酮。所得的 2-吡喃酮与由邻甲硅烷基芳基三氟甲磺酸酯生成的各种芳基中间体顺利反应，通过 Diels-Alder 反应和随后的脱羧芳构化提供多取代的萘​​。2-吡喃酮的芳炔反应通过与4-叠氮基-2-吡喃酮的三唑形成结合，用于合成具有1,2,3-三唑部分的多种萘。
• [Pd(PPh3)2(saccharinate)2]—general catalyst for Suzuki–Miyaura, Negishi cross-coupling and C–H bond functionalization of coumaryl and pyrone substrates
  作者：Parin Shah、M. Dolores Santana、Joaquín García、J. Luis Serrano、Minal Naik、Suhas Pednekar、Anant R. Kapdi

  DOI：10.1016/j.tet.2012.12.030

  日期：2013.2

  The potential of complex [Pd(PPh3)(2)(saccharinate)(2)] 1 in catalyzing Suzuki-Miyaura cross-coupling of 4-halo and 4-bromomethyl coumaryl and pyrone substrates with different aryl boronic acids has been explored. Excellent yields of the desired products are obtained in competitive reaction time and under relatively mild conditions. Negishi cross-coupling of 4-coumaryl tosylate with aryl and allcylzinc reagents has also been performed with good yields of the cross-coupled products obtained in most cases. Intramolecular C-H bond functionalization of coumaryl ethers also furnished very high yields of synthetically attractive tetracyclic ring systems exhibiting the potential of I as a powerful catalyst in synthetically important reactions. (C) 2012 Elsevier Ltd. All rights reserved.
• Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C–OH bond activation
  作者：Yi Hu、Qiuping Ding、Shengqing Ye、Yiyuan Peng、Jie Wu

  DOI：10.1016/j.tet.2011.07.048

  日期：2011.9

  An efficient palladium-catalyzed cross-coupling reaction of 4-hydroxy-pyrone or 4-hydroxy-2(5H)-furanone with arylboronic acid is described, which affords the 4-substituted-pyrones and 2(5H)-furanones in good yields. This transformation proceeds through a C-OH bond activation under mild conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• The First Selenium Isologues of 2-Pyrones and Coumarins: Synthesis, Structures, and Reactions
  作者：Toshiaki Murai、Akihito Yoshida、Tomohiko Mizutani、Hiroaki Kubuki、Kirara Yamaguchi、Toshifumi Maruyama、Fumitoshi Shibahara

  DOI：10.1246/cl.170341

  日期：2017.7.5

  The reactions of 2-pyrones and coumarins with hydrochlorosilane, elemental selenium, and 4-dimethylaminopyridine (DMAP) gave 2-selenopyrones and selenocoumarins in moderate to good yields. Their fo...

  2-吡喃酮和香豆素与氢氯硅烷、元素硒和 4-二甲氨基吡啶 (DMAP) 的反应以中等至良好的产率得到 2-硒吡喃酮和硒香豆素。他们的...