5-(3-methoxyphenyl)-pent-2-en-4-ynoic acid butyl ester | 1041003-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3-methoxyphenyl)-pent-2-en-4-ynoic acid butyl ester
• 英文别名: butyl (E)-5-(3-methoxyphenyl)pent-2-en-4-ynoate
• CAS: 1041003-20-6
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: OQIDEKGCADNNGV-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-(1,2-diiodovinyl)-3-methoxybenzene 、 丙烯酸丁酯 在 hydroxyapatite-supported palladium(II) complex N-甲基吗啉 、 potassium carbonate 作用下， 反应 6.0h， 以85%的产率得到5-(3-methoxyphenyl)-pent-2-en-4-ynoic acid butyl ester
  参考文献：
  名称：

  Hydroxyapatite-Supported Palladium-Catalyzed Efficient Synthesis of (E)-2-Alkene-4-ynecarboxylic Esters. Intense Fluorescene Emission of Selected Compounds

  摘要：

  A simple procedure for the synthesis of substituted (E)-2-alkene-4-ynecarboxylic esters has been achieved using hydroxyapatite-supported palladium as efficient catalyst surface. The catalyst is recycled, and the turnover number (TON) based on Pd is 16000. A naphthyl-substituted derivative gives very intense fluorescence emission.

  DOI：

  10.1021/jo800209z

文献信息

• Synthesis of substituted acetylenes, aryl–alkyl ethers, 2-alkene-4-ynoates and nitriles using heterogeneous mesoporous Pd-MCM-48 as reusable catalyst
  作者：Subhash Banerjee、Hari Khatri、Vagulejan Balasanthiran、Ranjit T. Koodali、Grigoriy Sereda

  DOI：10.1016/j.tet.2011.05.132

  日期：2011.8

  Pd-MCM-48 has been employed as a heterogeneous catalyst for the synthesis of substituted acetylenes via Sonogashira reactions under copper and amine-free reaction conditions. In addition, the catalyst exhibited excellent regioselectivity for primary alcohols towards C-O coupling leading to formation of alkyl aryl ethers in high yields. A green procedure for the stereoselective synthesis of 2-alkene-4-ynoates and nitriles from the reactions of vic-(E)-diiodoalkenes with activated alkenes has also been demonstrated using Pd-MCM-48 catalyst. The catalyst was easily recovered from the reaction mixture by filtration and reused for at least six times with minimal loss of activity. (C) 2011 Elsevier Ltd. All rights reserved.