(E)-1-hexen-2-yl 4-acetoxybenzoate | 1137972-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (E)-1-hexen-2-yl 4-acetoxybenzoate
• CAS: 1137972-63-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: QRCFPOMAXZKHHD-IZZDOVSWSA-N

物化性质

• 沸点：
  372.5±34.0 °C(predicted)
• 密度：
  1.087±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-乙酰氧基苯甲酸 、 1-己炔 在 [RuCl₂(p-cymene)(P(Fur)3)] 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.33h， 生成 (Z)-1-hexen-2-yl 4-acetoxybenzoate 、 (E)-1-hexen-2-yl 4-acetoxybenzoate 、 hex-1-en-2-yl 4-acetoxybenzoate
  参考文献：
  名称：

  微波催化钌催化羧酸与炔烃加成合成乙烯基酯

  摘要：

  描述了一种快速有效的方法，用于通过微波促进羧酸加成至末端炔烃来选择性合成烯醇酯。该方法使用易于获得的[RuCl 2（对-cymene）（PPh 3）]络合物作为催化剂，无需碱，反应在20分钟内完成。

  DOI：

  10.1071/ch08480

文献信息

• Synthesis and Catalytic Evaluation of Ruthenium–Arene Complexes Bearing Imidazol(in)ium-2-thiocarboxylate Ligands
  作者：Morgan Hans、Quentin Willem、Johan Wouters、Albert Demonceau、Lionel Delaude

  DOI：10.1021/om2006529

  日期：2011.11.28

  iocarboxylate zwitterions bearing cyclohexyl, 2,4,6-trimethylphenyl (mesityl), or 2,6-diisopropylphenyl groups on their nitrogen atoms in CH2Cl2 at −20 °C. All the products were fully characterized by IR and NMR spectroscopy, and the molecular structures of [RuCl2(p-cymene)(SOC·IMes)] (3) and [RuCl2(p-cymene)(SOC·SIMes)] (5) were determined by X-ray diffraction analysis. Coordination of the NHC·COS

  与通式五个新络合物将[RuCl 2（p -cymene）（SOC · NHC）]（2 - 6）通过将[RuCl反应以高收率进行分离2（p -cymene）] 2二聚体与一系列咪唑的在-20°C下，CH 2 Cl 2中氮原子上带有环己基，2,4,6-三甲基苯基（甲磺酰基）或2,6-二异丙基苯基的（二）2-硫代羧酸盐两性离子。所有产物均通过IR和NMR光谱进行了充分表征，[RuCl 2（p- Cymene）（SOC · IMes）]（3）和[RuCl通过X射线衍射分析确定了2（对-异丙基）（SOC · SIMes）]（5）。NHC · COS配体通过硫原子进行配位。上的次甲基质子的一个显着屏蔽p通过观察-cymene异丙基1个H NMR光谱对络合物3 - 6。这很可能是由相邻的1,3,6-二异丙基苯基取代基的芳环电流引起的。化合物2 – 6的催化活性在环辛烯的开环复分解聚合（ROMP），甲基丙
• Novel, Highly Efficient and Selective Ruthenium Catalysts for the Synthesis of Vinyl Esters from Carboxylic Acids and Alkynes
  作者：François Nicks、Rosario Aznar、Daniel Sainz、Guillermo Muller、Albert Demonceau

  DOI：10.1002/ejoc.200900697

  日期：2009.10

  An efficient and highly selective synthesis of vinyl esters was developed that employed carboxylic acids and terminal alkynes as reagents, and novel tethered (η1:η6-phosphanoarene)ruthenium complexes as catalyst precursors. With these catalyst systems, the reactions were somewhat slower than when using the best catalysts reported to date, but the selectivities were excellent with up to 98 % of the

  开发了一种高效且高选择性的乙烯基酯合成方法，其使用羧酸和末端炔作为试剂，并使用新型系链 (η1:η6-膦芳基) 钌配合物作为催化剂前体。使用这些催化剂体系时，反应比使用迄今为止报道的最佳催化剂时稍慢，但选择性非常好，马尔可夫尼科夫异构体高达 98%。此外，这些催化剂的营业额 (TON) 为 5000，大大优于竞争对手。微量的水对反应速率有有益的影响，同时保持相同的选择性。此外，160 °C 的微波加热也大大加速了反应，尽管会损害选择性。最后，
• Catalytic activity assessment of [RuCl2 (p-cymene) (PTA)] in the synthesis of enol esters
  作者：Eric Musengimana、Claver Fatakanwa

  DOI：10.1007/s13738-015-0732-7

  日期：2016.2

  The addition of carboxylic acids onto 1-hexyne was catalyzed by [RuCl2 (p-cymene) (PTA)] complex to give enol esters. Accordingly, the Markovnikov addition-type product was selectively obtained. The microwave-assisted reactions at 160 °C confirmed the influence of the temperature, where quantitative to excellent yields were obtained in 30 min. The catalyst loading test proved that [RuCl2 (p-cymene) (PTA)] complex can be efficiently used with a 1/1500 ratio to carboxylic acid providing the TON value of 1500.

  通过催化[RuCl2 (p-cymene) (PTA)]复合物将羧酸加成到1-己炔，生成烯醇酯。因此，选择性获得了马尔科尼科夫加成型产物。160°C的微波辅助反应确认了温度的影响，30分钟内获得了定量到优异的产率。催化剂负载测试证明[RuCl2 (p-cymene) (PTA)]复合物可以高效地以1/1500的比例与羧酸结合，提供了1500的单位转化数（TON）。
• Ruthenium–arene complexes bearing imidazol(in)ium-2-dithiocarboxylate ligands: Evaluation of their catalytic activity in the synthesis of enol esters
  作者：Quentin Willem、François Nicks、Xavier Sauvage、Lionel Delaude、Albert Demonceau

  DOI：10.1016/j.jorganchem.2009.08.028

  日期：2009.12

  The catalytic activity of four ruthenium imidazol(in)ium-2-dithiocarboxylates was evaluated for the synthesis of vinyl esters through addition of 4-acetoxybenzoic acid to 1-hexyne, and compared to those of the parent ruthenium-N-heterocyclic carbene complexes and [RuCl2(p-cymene)(PPh3)] (a standard catalyst). It turned out that ruthenium imidazol(in)ium-2-dithiocarboxylates were poorly active and selective. Quantitative yields, indeed, were obtained only after extended reaction times. However, the catalytic activity could be improved significantly under microwave heating or conventional heating in a sealed tube at 160 degrees C, driving the reaction to completion in less than 4 h of reaction. (C) 2009 Elsevier B. V. All rights reserved.