4-(hex-1-yn-1-yl)furan-2(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-(hex-1-yn-1-yl)furan-2(5H)-one
• 英文别名: 4-(hex-1-ynyl)-2(5H)-furanone；3-hex-1-ynyl-2H-furan-5-one
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: GSNIBAOLPVFASK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-oxo-2,5-dihydrofuran-3-yl 4-nitrobenzenesulfonate 、 1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以83%的产率得到4-(hex-1-yn-1-yl)furan-2(5H)-one
  参考文献：
  名称：

  乙烯基磺酸盐：钯催化交叉偶联反应的理想伴侣

  摘要：

  赶紧离开！在各种钯催化的交叉偶联反应中，如Suzuki，Stille，Heck和Sonogashira反应（参见方案），Nosylates都是极好的离去基团。结晶，稳定且便宜的乙烯基和芳基壬酸酯被证明比传统的卤化物和三氟甲磺酸酯更好，始终提供更高的偶联产物收率。它们的有用性用C  C键的形成也是由生物碱dubamine的快速合成证明。

  DOI：

  10.1002/chem.201300127

文献信息

• Vinyl Nosylates: An Ideal Partner for Palladium-Catalyzed Cross-Coupling Reactions
  作者：Nicolas P. Cheval、Anna Dikova、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1002/chem.201300127

  日期：2013.7.1

  In a hurry to leave! Nosylates act as an excellent leaving group in various palladium‐catalyzed cross‐couplings, such as Suzuki, Stille, Heck, and Sonogashira reactions (see scheme). Crystalline, stable, and cheap vinyl and aryl nosylates proved better than classical halides and triflates, consistently giving higher yields of coupling products. Their usefulness in CC bond formation was also demonstrated

  赶紧离开！在各种钯催化的交叉偶联反应中，如Suzuki，Stille，Heck和Sonogashira反应（参见方案），Nosylates都是极好的离去基团。结晶，稳定且便宜的乙烯基和芳基壬酸酯被证明比传统的卤化物和三氟甲磺酸酯更好，始终提供更高的偶联产物收率。它们的有用性用C  C键的形成也是由生物碱dubamine的快速合成证明。
• Syntheses of 4-(1-alkynyl)-2(5H)-furanones and coumarins via the palladium catalyzed cross-coupling reactions of potassium alkynyltrifluoroborates
  作者：George W. Kabalka、Gang Dong、Bollu Venkataiah

  DOI：10.1016/j.tetlet.2004.04.150

  日期：2004.6

  An efficient synthesis of 4-(1-alkynyl)-2(5H)-furanones has been developed utilizing a palladium catalyzed coupling reaction of β-tetronic acid bromide with potassium alkynyltrifluoroborates in the absence of base. 4-Alkynylcoumarins were also synthesized using this method. The reactions are straightforward and the yields are excellent.

  在不存在碱的情况下，利用β-四氢硼酸溴化物与炔基三氟硼酸钾的钯催化偶合反应，已开发出4-（1-炔基）-2（5H）-呋喃酮的有效合成方法。还使用该方法合成了4-炔基香豆素。反应简单，收率优异。
• Selective palladium-mediated synthesis of racemic 4,5-disubstituted 5H-furan-2-ones from 3-ynoic acids and organic halides
  作者：Renzo Rossi、Fabio Bellina、Matteo Biagetti、Luisa Mannina

  DOI：10.1016/s0040-4039(98)01652-9

  日期：1998.10

  Racemic 4,5-disubstitued 5H-furan-2-ones have been selectively synthesized by addition of 1.2-1.6 equiv of aryl, alkenyl or 1-alkynyl halides and catalytic amounts of Pd(OAc)(2) and a soft ligand such as tri-2-furylphosphine or triphenylarsine to the reaction mixtures obtained by treatment of 3-ynoic acids with 1.1 equiv of t-BuOK in DMSO at 20 degrees C. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions
  作者：Nicolas P. Cheval、Barbara Hoffmann、Anna Dikova、Fatih Sirindil、Philippe Bertus、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1016/j.tet.2018.10.017

  日期：2018.12

  Vinyl nosylates, readily obtained from β-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, either cocatalyzed by copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). These new leaving group and mild conditions could be applied to the synthesis of acetylenic

  容易从β-二羰基衍生物中获得的乙烯基Nosylates，可以有效地参与Sonogashira交叉偶联反应，可以通过铜盐或银盐共同催化。的对位-nitrobenzenesulfonate（硝基苯磺酸酯）基团可以在非常温和条件下（室温）下进行该偶联。这些新的离去基团和温和的条件可用于炔属香豆素衍生物的合成以及炔属单萜天然产物氯维立利德的总合成。