hex-1-en-2-yl-4-methoxy benzoate

• 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: hex-1-en-2-yl-4-methoxy benzoate
• 英文别名: Hex-1-en-2-yl 4-methoxybenzoate
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: MRQZVIWMVOCILJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  大茴香酸 、 1-己炔 在 dichlororuthenium(II) (p-cymene)(1,3,5-triaza-7-phosphaadamantane) 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 100.0h， 以46%的产率得到hex-1-en-2-yl-4-methoxy benzoate
  参考文献：
  名称：

  Catalytic activity assessment of [RuCl2 (p-cymene) (PTA)] in the synthesis of enol esters

  摘要：

  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）。

  DOI：

  10.1007/s13738-015-0732-7

文献信息

• Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl estersWe thank Prof. Dr. M. T. Reetz for generous support and constant encouragement, and gratefully acknowledge the DFG, the FCI, and the BMBF for financial support.
  作者：Lukas J. Goossen、Jens Paetzold、Debasis Koley

  DOI：10.1039/b211277a

  日期：2003.3.6

  The catalytic activity of commercially available, air and water stable ruthenium complexes in the addition of carboxylic acids to terminal alkynes was found to be drastically enhanced by the addition of small quantities of base. Moreover, the regioselectivity of the reaction can be controlled by the choice of the base so that both the Markovnikov (Na2CO3) and the anti-Markovnikov products (DMAP) are now easily accessible in excellent selectivities.

  商业可得的，在空气和水中稳定的钌配合物在羧酸与末端炔烃加成反应中的催化活性，采用少量碱的添加后显著增强。此外，反应的区域选择性可以通过选择不同的碱来控制，从而使得Markovnikov（Na2CO3）和反Markovnikov产物（DMAP）都能以优良的选择性轻松获得。
• Microwave-Assisted Synthesis of Vinyl Esters through Ruthenium-Catalyzed Addition of Carboxylic Acids to Alkynes
  作者：François Nicks、Lionel Libert、Lionel Delaude、Albert Demonceau

  DOI：10.1071/ch08480

  日期：——

  A rapid and efficient method is described for the selective synthesis of enol esters via the microwave-accelerated addition of carboxylic acids to terminal alkynes. The method employs the readily available [RuCl2(p-cymene)(PPh3)] complex as catalyst without the need of bases, and reactions are complete in 20 min.

  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。
• 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，
• Copper porphyrin as efficient catalysts for esterification of allyl sp3 C H bond with carboxylic acid
  作者：Ming-Feng Xiong、Atif Ali、Waseem Akram、Hao Zhang、Li-Ping Si、Hai-Yang Liu

  DOI：10.1016/j.catcom.2019.04.001

  日期：2019.5

  We described that copper 5,10,15,20-tetrakis (ethoxycarbonyl)porphyrin (TECP) catalyzed oxidative cross dehydrogenative coupling of allyl sp3 CH bond with acid for the synthesis of allyl esters in a homogeneous system. This reaction proceeded with broad substrate scope and good functional group tolerance. In the gram-level test, the turnover number (TON) reached to 8100 at 0.01 mol% catalyst loading

  我们描述了5,10,15,20-四（乙氧基羰基）卟啉铜（TECP）催化烯丙基sp 3 C H键与酸的氧化交叉脱氢偶联，用于在均相系统中合成烯丙基酯。该反应在宽的底物范围和良好的官能团耐受性下进行。在克级测试中，在催化剂负载量为0.01 mol％时，周转率（TON）达到8100，产率为81％。
• Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes
  作者：Bathoju Chandra Chary、Sunggak Kim

  DOI：10.1021/jo101543q

  日期：2010.11.19

  Au(I)-catalyzed hydroacyloxylation of alkynes with carboxylic acids is described PPh3AuCl/AgPF6 catalyst affords the Markonikov addition products, whereas PPh3AuCl/AgOTf catalyst gives the more stable isomerized products via the Markonikov products