6,7-dimethyl-4-tosyloxycoumarin | 879416-91-8

• 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: 6,7-dimethyl-4-tosyloxycoumarin
• 英文别名: 6,7-Dimethyl-2-oxo-2H-1-benzopyran-4-yl 4-methylbenzene-1-sulfonate；(6,7-dimethyl-2-oxochromen-4-yl) 4-methylbenzenesulfonate
• CAS: 879416-91-8
• 化学式: C₁₈H₁₆O₅S
• 分子量: 344.388
• InChiKey: YOLZBMOUUKIMMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-dimethyl-4-tosyloxycoumarin 、 triphenylindium 在 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到6,7-二甲基-4-苯基色烯-2-酮
  参考文献：
  名称：

  An efficient route to 4-substituted coumarins, 2(5H)-furanones, and pyrones via palladium-catalyzed couplings of alkenyl tosylates with organoindium reagents

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.10.096
• 作为产物：
  描述：

  4-羟基-6,7-二甲基香豆素 、 对甲苯磺酰氯 在 三乙胺 作用下， 生成 6,7-dimethyl-4-tosyloxycoumarin
  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）
• 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。
• Palladium-catalyzed Suzuki–Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one
  作者：Jie Wu、Liang Zhang、Hong-Guang Xia

  DOI：10.1016/j.tetlet.2006.01.020

  日期：2006.3

  Pd(PPh3)4 catalyzed Suzuki–Miyaura cross-coupling reactions of 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one with various potassium aryl trifluoroborates afforded the corresponding 4-substituted coumarins or 4-substituted quinolin-2(1H)-ones in good to excellent yield.

  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。
• 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.