(Z)-5-(2-(4-methoxybenzyloxy)ethylidene)furan-2(5H)-one | 1188414-02-9

• 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-(4-methoxybenzyloxy)ethylidene)furan-2(5H)-one
• 英文别名: (5Z)-5-[2-[(4-methoxyphenyl)methoxy]ethylidene]furan-2-one
• CAS: 1188414-02-9
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: KKXKNWOKJOIBMB-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-3-碘丙烯酸 、 1-甲氧基-4-甲基苯基炔丙基醚 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 以70%的产率得到(Z)-5-(2-(4-methoxybenzyloxy)ethylidene)furan-2(5H)-one
  参考文献：
  名称：

  Pd/C–Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

  摘要：

  10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of gamma-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.040

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.
• Pd/C–Cu mediated direct and one-pot synthesis of γ-ylidene butenolides
  作者：D. Rambabu、S. Bhavani、Kumara Swamy Nalivela、Soumita Mukherjee、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2013.02.040

  日期：2013.4

  10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of gamma-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry. (C) 2013 Elsevier Ltd. All rights reserved.