ethyl (2Z)-3-phenylnon-2-en-4-ynoate | 911047-11-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-3-phenylnon-2-en-4-ynoate
• 英文别名: ethyl (Z)-3-phenylnon-2-en-4-ynoate
• CAS: 911047-11-5
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: SMBYHGYUBVZUEL-JQIJEIRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-3-phenylnon-2-en-4-ynoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 3-phenyl-2-nonen-4-ynal
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q
• 作为产物：
  描述：

  苯丙炔酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溶剂黄146 、 三乙胺 、 sodium iodide 作用下， 反应 6.17h， 生成 ethyl (2Z)-3-phenylnon-2-en-4-ynoate
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q

文献信息

• Palladium-Catalyzed One-Pot Highly Regioselective 6-<i>Endo</i> Cyclization and Alkylation of Enynoates: Synthesis of 2-Alkanone Pyrones
  作者：Tanveer Ahmad、Sheng-Qi Qiu、Yun-He Xu、Teck-Peng Loh

  DOI：10.1021/acs.joc.8b02198

  日期：2018.11.2

  The Pd(II)-catalyzed one-pot tandem cyclization/alkylation reactions of enynoates with allylic alcohols have been demonstrated. In this reaction, an innovative protocol proceeded well through Pd-catalyzed intramolecular selective 6-endo cyclization, insertion of allylic alcohols into the Pd–C bond of vinylpalladium species generated in situ, and β-hydrogen elimination processes. This conversion provides

  烯醇与烯丙基醇的Pd（II）催化一锅串联串联环化/烷基化反应已得到证明。在该反应中，一种创新的协议，通过进行公Pd催化的分子内选择性6-内环化，烯丙基醇成原位生成的vinylpalladium物种，和β氢消除过程的的Pd-C键的插入。该转化为中等产率至良好产率的2-链烷酮吡喃酮的合成提供了方便而有效的方法。
• Palladium-Catalyzed Cascade Intramolecular Cyclization and Allylation of Enynoates with Allylic Alcohols
  作者：Sheng-Qi Qiu、Tanveer Ahmad、Yun-He Xu、Teck-Peng Loh

  DOI：10.1021/acs.joc.9b00461

  日期：2019.6.7

  A Pd(II)-catalyzed mild and highly regioselective 6-endo cyclization/allylation reaction of enynoates with simple allylic alcohols has been developed. Under mild reaction conditions, the vinyl palladium species generated in situ after cyclization could insert C–C double bond of allylic alcohol through cross-coupling reaction and lead to the formation of allyl pyrone via β-OH elimination. This cascade

  钯（II）催化的温和和高度选择性6-内用简单的烯丙基醇enynoates的环化/烯丙基化反应已经研制成功。在温和的反应条件下，环化后原位生成的乙烯基钯物种可通过交叉偶联反应插入烯丙基醇的C–C双键，并通过β-OH消除导致烯丙基吡喃形成。该级联交叉偶联反应代表了以中等至良好收率构建新型烯丙基吡喃酮的直接和原子经济的方法。
• Preparation and decarboxylative rearrangement of (Z)-enyne esters
  作者：Jacqueline C.S. Woo、Shawn D. Walker、Margaret M. Faul

  DOI：10.1016/j.tetlet.2007.06.012

  日期：2007.8

  A method to assemble (Z)-enyne esters via palladium-catalyzed cross coupling reactions of enol tosylates is reported. A base-mediated one-pot decarboxylative rearrangement of the enynes to enones is described. The scope of this process is examined. (c) 2007 Elsevier Ltd. All rights reserved.
• Research on a compact adsorption room air conditioner
  作者：G.Z. Yang、Z.Z. Xia、R.Z. Wang、Daou Keletigui、D.C. Wang、Z.H. Dong、X. Yang

  DOI：10.1016/j.enconman.2005.12.005

  日期：2006.9

  A novel compact adsorption room air conditioner with a cooling capacity of 1 kW has been designed, and two prototypes have been built. A two bed, continuous adsorption refrigeration cycle with heat recovery and mass recovery is adopted. Micropore spherical silica gel and water are selected as the working pair. A gravity heat pipe with methanol as working medium is designed to output the cooling. Experimental investigations have indicated that under typical air conditioning conditions, for the first prototype, a cooling capacity of 687 W and a COP (coefficient of performance) of 0.307 can be obtained. However, for the improved one, a cooling capacity of 790 W and a COP of 0.446 can be reached. It is also proved that the operating temperatures have strong influences on the performance. The designed room air conditioner can be driven by a low grade heat source (< 90 degrees C) and has small dimensions of 300 mm (depth), 500 mm (width) and 950 mm (height). (c) 2006 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Alkoxycarbonylation of (<i>Z</i>)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates
  作者：G. Eray Akpınar、Melih Kuş、Muhammed Üçüncü、Erman Karakuş、Levent Artok

  DOI：10.1021/ol102989q

  日期：2011.2.18

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.