(Z)-5-(2-methylbenzylidene)-4-methylfuran-2(5H)-one | 1188413-95-7

• 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: (Z)-5-(2-methylbenzylidene)-4-methylfuran-2(5H)-one
• 英文别名: (Z)-4-methyl-5-(2-methylbenzylidene)furan-2(5H)-one；(5Z)-4-methyl-5-[(2-methylphenyl)methylidene]furan-2-one
• CAS: 1188413-95-7
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: YXOKDVLTYCVUON-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 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：
  2

反应信息

• 作为产物：
  描述：

  2-乙炔基甲苯 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 (IPr)AgCl 、 二异丙胺 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、1.0 MPa 条件下， 反应 52.0h， 生成 (Z)-5-(2-methylbenzylidene)-4-methylfuran-2(5H)-one 、 4-methyl-6-(2-methylphenyl)-2H-pyran-2-one
  参考文献：
  名称：

  SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives

  摘要：

  C-C bond forming carboxylation, and cyclization: of trimethyl(2-rnethylenbut-3,7yl)silaile derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the:corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2:furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig-cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.

  DOI：

  10.1021/acs.orglett.5b03023

文献信息

• Copper-Catalyzed Preparation of γ-Alkylidenebutenolides and Isocoumarins under Mild Palladium-Free Conditions
  作者：Samuel Inack-Ngi、Raphaël Rahmani、Laurent Commeiras、Gaëlle Chouraqui、Jérôme Thibonnet、Alain Duchêne、Mohamed Abarbri、Jean-Luc Parrain

  DOI：10.1002/adsc.200800757

  日期：2009.3

  Abstractmagnified imageA general and efficient copper(I)‐catalyzed cross‐coupling and heterocyclization reaction of terminal alkynes and β‐iodo‐α,β‐unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5‐ylidenebutenolides and 3‐substituted isocoumarins with excellent regio‐ and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium‐free.