4-(4-fluorophenyl)-6-methyl-2H-chromen-2-one | 879416-96-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(4-fluorophenyl)-6-methyl-2H-chromen-2-one
• 英文别名: 2H-1-Benzopyran-2-one, 4-(4-fluorophenyl)-6-methyl-；4-(4-fluorophenyl)-6-methylchromen-2-one
• CAS: 879416-96-3
• 化学式: C₁₆H₁₁FO₂
• 分子量: 254.261
• InChiKey: YAONVVLBLBMRSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  398.4±42.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基香豆素 在 四(三苯基膦)钯 、 caesium carbonate 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 生成 4-(4-fluorophenyl)-6-methyl-2H-chromen-2-one
  参考文献：
  名称：

  钯催化的三氟硼酸钾芳基与4-甲苯磺酰香豆素或4-甲苯磺酰喹啉-2（1 H）-的Suzuki-Miyaura偶联

  摘要：

  Pd（PPh 3）4催化4-甲苯磺酰香豆素或4-甲苯磺酰喹啉-2（1 H）-之一与各种芳基三氟硼酸钾盐的Suzuki-Miyaura交叉偶联反应，得到相应的4-取代香豆素或4-取代喹啉-2（ 1 H）-良至优异的收率。

  DOI：

  10.1016/j.tetlet.2006.01.020

文献信息

• RhCl(PPh3)3/DPPF: A Useful and Efficient Catalyst for Cross-Coupling Reactions of Activated Alkenyl Tosylates with Arylboronic Acids
  作者：Jie Wu、Liang Zhang、Ke Gao

  DOI：10.1002/ejoc.200600469

  日期：2006.12

  Suzuki–Miyaura cross-coupling of activated alkenyl tosylates is described. The results not only represent the first examples of the rhodium-catalyzed Suzuki–Miyaura coupling of activated alkenyl tosylates with arylboronic acids under mild conditions, but also provide an efficient route for the synthesis of some natural product-like compounds, such as furan-2(5H)-one, coumarin, pyrone, and quinolin-2(1H)-one

  描述了一种有用且有效的铑催化剂体系 - [RhCl(PPh3)3/DPPF] - 用于活化甲苯磺酸烯基酯的 Suzuki-Miyaura 交叉偶联。该结果不仅代表了在温和条件下活化的甲苯磺酸烯基与芳基硼酸在铑催化下 Suzuki-Miyaura 偶联的第一个例子，而且还为合成一些天然产物类化合物（如呋喃-2）提供了有效途径。 (5H)-one、香豆素、吡喃酮和喹啉-2(1H)-one 衍生物。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006）
• Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
  作者：Maddali L.N. Rao、Abhijeet Kumar

  DOI：10.1016/j.tet.2014.07.059

  日期：2014.9

  4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2–4 h conditions

  在钯催化下，使用三芳基铋作为三重芳基化试剂，研究了不同取代的4-氯香豆素的交叉偶联反应。证明了4-氯香豆素的高反应性以化学选择性方式递送单芳基化和双芳基化产物。所采用的反应条件简单，稳定，并且在2-4小时的条件下，三芳基铋试剂的三重偶联反应性得到了良好的证明。在合成一些天然存在的新黄酮（3.27 – 3.30）中探索了该方法的实用性。另外，4-芳基香豆素3.1产物是制备（R）-托特罗定的有用前体。
• Palladium-Catalyzed Synthesis of 4-Arylcoumarins Using Triarylbismuth Compounds as Atom-Efficient Multicoupling Organometallic Nucleophiles
  作者：Maddali L. N. Rao、Varadhachari Venkatesh、Deepak N. Jadhav

  DOI：10.1002/ejoc.201000134

  日期：——

  Triarylbismuth compounds have been cross-coupled as atom-efficient multicoupling organometallic nucleophiles with 4-bromo- and 4-(trifluoromethylsulfonyloxy)coumarins under palladium catalysis conditions. These reactions afforded an array of 4-arylcoumarins in high yields. The general palladium protocol has been demonstrated to be efficient for the coupling of both bromide and triflate derivatives

  在钯催化条件下，三芳基铋化合物作为原子高效多偶联有机金属亲核试剂与 4-溴和 4-（三氟甲基磺酰氧基）香豆素交叉偶联。这些反应以高产率提供了一系列 4-芳基香豆素。通用钯方案已被证明对于香豆素的溴化物和三氟甲磺酸酯衍生物与三芳基铋试剂的偶联是有效的。
• Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates
  作者：Jie Wu、Liang Zhang、Yong Luo

  DOI：10.1016/j.tetlet.2006.07.085

  日期：2006.9

  RhCl(PPh3)3/DPPF was successfully employed as an efficient catalyst in the Suzuki–Miyaura cross-coupling reactions of potassium aryltrifluoroborates with alkenyl tosylates, affording the corresponding products in good to excellent yields.

  RhCl（PPh 3）3 / DPPF已成功地用作芳基三氟硼酸钾与烯基甲苯磺酸盐的Suzuki-Miyaura交叉偶联反应的有效催化剂，以良好的收率获得了相应的产物。
• An efficient route to 4-substituted coumarins, 2(5H)-furanones, and pyrones via palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents
  作者：Wei Gao、Yong Luo、Qiuping Ding、Yiyuan Peng、Jie Wu

  DOI：10.1016/j.tetlet.2009.10.096

  日期：2010.1

  Highly efficient palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents under mild conditions are described, which give rise to 4-substituted coumarins, 2(5H)-furanones, and pyrones in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.