5-phenyl-pent-2-en-4-ynoic acid butyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-phenyl-pent-2-en-4-ynoic acid butyl ester
• 英文别名: butyl (E)-5-phenylpent-2-en-4-ynoate
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: SYUZPLHIJYIBJE-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  苯乙烯 在 四丁基溴化铵 、 碘 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 5-phenyl-pent-2-en-4-ynoic acid butyl ester
  参考文献：
  名称：

  Synthesis of substituted acetylenes, aryl–alkyl ethers, 2-alkene-4-ynoates and nitriles using heterogeneous mesoporous Pd-MCM-48 as reusable catalyst

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.05.132

文献信息

• A New Route to the Synthesis of (<i>E</i>)- and (<i>Z</i>)-2-Alkene-4-ynoates and Nitriles from <i>vic</i>-Diiodo-(<i>E</i>)-alkenes Catalyzed by Pd(0) Nanoparticles in Water
  作者：Brindaban C. Ranu、Kalicharan Chattopadhyay

  DOI：10.1021/ol0708121

  日期：2007.6.1

  and (Z)-2-alkene-4-ynoates and -nitriles by a simple reaction of vic-diiodo-(E)-alkenes with acrylic esters and nitriles catalyzed by in situ prepared Pd(0) nanoparticles in water has been developed. Addition of acrylic esters leads to (E)-isomers exclusively, whereas (Z)-isomers are obtained in high stereoselectivity from reactions of acrylonitrile. The aqueous slurry of Pd nanoparticles is recycled

  通过vic-二碘代-（E）-烯烃与丙烯酸酯和腈原位催化的简单反应，立体选择性合成（E）-和（Z）-2-烯基-4-炔酸酯和-腈的有效方法已开发出在水中制备的Pd（0）纳米粒子。丙烯酸酯的添加仅导致（E）-异构体，而从丙烯腈的反应以高立体选择性获得（Z）-异构体。钯纳米颗粒的水浆液被回收。已经提出了一种可能的机制。
• Hydroxyapatite-Supported Palladium-Catalyzed Efficient Synthesis of (<i>E</i>)-2-Alkene-4-ynecarboxylic Esters. Intense Fluorescene Emission of Selected Compounds
  作者：Brindaban C. Ranu、Laksmikanta Adak、Kalicharan Chattopadhyay

  DOI：10.1021/jo800209z

  日期：2008.7.1

  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.
• Palladium-Catalyzed Oxidative Alkynylation of Alkenes via C−C Bond Cleavage under Oxygen Atmosphere
  作者：Takahiro Nishimura、Hitoshi Araki、Yasunari Maeda、Sakae Uemura

  DOI：10.1021/ol0348405

  日期：2003.8.1

  graphicPalladium-catalyzed oxidative alkynylation of alkenes using tert-propargylic alcohols as alkynylation reagents via C-C bond cleavage under an oxygen atmosphere affords the corresponding ene-yne compounds.
• 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.