(Z)-tridec-8-en-1-yl acetate

• 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: (Z)-tridec-8-en-1-yl acetate
• 英文别名: 8Z-Tridecenyl acetate；[(Z)-tridec-8-enyl] acetate
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: PXLZBHTYUDYDTH-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  5-癸烯 在 (pivalate)(o-isopropoxyphenylmethylene)(1,3-di(2,4,6-trimethylphenyl)imidazolidin-2-yl-H)ruthenium 、 [Ru(pivalate)(CHC6H4OiPr)(C10H14C3H4N2Mes)] 作用下， 以 四氢呋喃 为溶剂， 35.0 ℃ 、506.66 kPa 条件下， 反应 6.0h， 生成 (Z)-tridec-8-en-1-yl acetate
  参考文献：
  名称：

  Z-Selective Ethenolysis with a Ruthenium Metathesis Catalyst: Experiment and Theory

  摘要：

  The Z-selective ethenolysis activity of chelated ruthenium metathesis catalysts was investigated with experiment and theory. A five-membered chelated catalyst that was successfully employed in Z-selective cross metathesis reactions has now been found to be highly active for Z-selective ethenolysis at low ethylene pressures, while tolerating a wide variety of functional groups. This phenomenon also affects its activity in cross metathesis reactions and prohibits crossover reactions of internal olefins via trisubstituted ruthenacyclobutane intermediates. In contrast, a related catalyst containing a six-membered chelated architecture is not active for ethenolysis and seems to react through different pathways more reminiscent of previous generations of ruthenium catalysts. Computational investigations of the effects of substitution on relevant transition states and ruthenacyclobutane intermediates revealed that the differences of activities are attributed to the steric repulsions of the anionic ligand with the chelating groups.

  DOI：

  10.1021/ja4010267

文献信息

• Improved Ruthenium Catalysts for <i>Z</i>-Selective Olefin Metathesis
  作者：Benjamin K. Keitz、Koji Endo、Paresma R. Patel、Myles B. Herbert、Robert H. Grubbs

  DOI：10.1021/ja210225e

  日期：2012.1.11

  carboxylate ligand and the aryl group of the N-heterocyclic carbene have been altered and the resulting catalysts evaluated using a range of metathesis reactions. Substitution of bidentate with monodentate X-type ligands led to a severe attenuation of metathesis activity and selectivity, while minor differences were observed between bidentate ligands within the same family (e.g., carboxylates). The use of nitrato-type

  已经合成了几种用于 Z-选择性烯烃复分解反应的新型 CH 活化钌催化剂。N-杂环卡宾的羧酸配体和芳基均已改变，并使用一系列复分解反应对所得催化剂进行了评估。用单齿X型配体取代双齿会导致复分解活性和选择性严重减弱，而同一家族内的双齿配体（例如，羧酸盐）之间观察到微小差异。使用硝基型配体代替羧酸盐显着提高了复分解活性和选择性。使用这些催化剂，各种交叉复分解反应的周转数可能接近 1000，包括工业相关产品的合成。
• Highly Active Ruthenium Metathesis Catalysts Exhibiting Unprecedented Activity and <i>Z</i>-Selectivity
  作者：Lauren E. Rosebrugh、Myles B. Herbert、Vanessa M. Marx、Benjamin K. Keitz、Robert H. Grubbs

  DOI：10.1021/ja311916m

  日期：2013.1.30

  A novel chelated ruthenium-based metathesis catalyst bearing an N-2,6-diisopropylphenyl group is reported and displays near-perfect selectivity for the Z-olefin (>95%), as well as unparalleled TONs of up to 7400, in a variety of homodimerization and industrially relevant metathesis reactions. This derivative and other new catalytically active species were synthesized using an improved method employing

  报道了一种带有 N-2,6-二异丙基苯基的新型螯合钌基复分解催化剂，它对 Z-烯烃表现出近乎完美的选择性 (>95%)，以及无与伦比的高达 7400 的 TONs，在各种同二聚化和工业相关的复分解反应。这种衍生物和其他新的催化活性物质是使用改进的方法合成的，该方法采用羧酸钠来诱导这些螯合配合物的盐复分解和 CH 活化。所有这些新型钌基催化剂在末端烯烃的均二聚反应中都具有高度的 Z 选择性。
• Continuous Flow <i>Z</i> ‐Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**
  作者：Jennifer Morvan、Tom McBride、Idriss Curbet、Sophie Colombel‐Rouen、Thierry Roisnel、Christophe Crévisy、Duncan L. Browne、Marc Mauduit

  DOI：10.1002/anie.202106410

  日期：2021.9

  The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times

  报道了第一个连续流动 Z-选择性烯烃复分解过程。Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. 设计的连续工艺允许各种自、交叉和大环闭环复分解反应，以高选择性和短停留时间提供产品。该技术通过直接应用于一系列信息素和大环气味分子的制备来举例说明，并在一个伸缩的 Z 选择性交叉复分解/迪克曼环化序列中达到高潮，以获取 ( Z )-Civetone，并结合一系列连续搅拌罐反应堆。
• [EN] Z-SELECTIVE METATHESIS CATALYSTS<br/>[FR] CATALYSEURS DE MÉTATHÈSE SÉLECTIFS POUR Z
  申请人：CALIFORNIA INST OF TECHN

  公开号：WO2014093687A1

  公开（公告）日：2014-06-19

  A novel chelated ruthenium-based metathesis catalyst bearing an N-2,6- diisopropylphenyl group is reported and displays near-perfect selectivity for the Z-olefin (>95%), as well as unparalleled TONs of up to 7,400, in a variety of homodimerization and industrially relevant metathesis reactions. This derivative and other new catalytically-active species were synthesized using an improved method employing sodium carboxylates to induce the salt metathesis and C-H activation of these chelated complexes. All of these new ruthenium-based catalysts are highly Z-selective in the homodimerization of terminal olefins.

  报告了一种含有N-2,6-二异丙基苯基团的新型螯合钌基烯烃复分解催化剂，该催化剂在多种同二聚和工业相关复分解反应中表现出对Z-烯烃的高选择性（>95%），并且具有无与伦比的转化数（TONs）高达7,400。使用改进的方法合成了这种衍生物和其他新的催化活性物种，该方法使用钠羧酸盐诱导这些螯合配合物的盐复分解和C-H活化。所有这些新的钌基催化剂在端烯烃的同二聚反应中都具有高度Z选择性。
• Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.
  作者：Michio HORIIKE、Masaru TANOUCHI、Chisato HIRANO

  DOI：10.1271/bbb1961.44.257

  日期：——

  (Z)-Alkenols and Their acetates have been synthesized by the Wittig reaction of (ω-hydroxyalkyl)triphenylphosphonium salts with alkanals by a convenient procedure. The geometrical purity of the products was evaluated to be no less than 95% of the (Z)-configu-ration by means of GLC with a glass capillary column coated with CHDMS.

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。