(Z)-1,3-diphenyl-1-triethylsilyloxy-1-propene | 82798-43-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-1,3-diphenyl-1-triethylsilyloxy-1-propene
• 英文别名: (Z)-(1,3-diphenylprop-1-enyloxy)triethylsilane；(Z)-1,3-diphenyl-1-triethylsiloxy-1-propene；[(Z)-1,3-diphenylprop-1-enoxy]-triethylsilane
• CAS: 82798-43-4
• 化学式: C₂₁H₂₈OSi
• 分子量: 324.538
• InChiKey: IBVYFUIDEFLXQY-UZYVYHOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基硅烷 、 苯亚甲基苯乙酮 在 SiO₂-supported palladium-gold alloy catalyst 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以38%的产率得到(Z)-1,3-diphenyl-1-triethylsilyloxy-1-propene
  参考文献：
  名称：

  支持的钯-金合金催化剂，在温和的条件下，以分离的单个钯原子在合金纳米颗粒中为主要活性部位，可进行高效且选择性的氢硅烷化

  摘要：

  负载型Pd-Au合金催化剂是为α，β-不饱和酮和炔烃的高效选择性氢化硅烷化而开发的。Pd–Au合金和载体材料的Pd / Au原子比影响催化活性，并且具有低Pd / Au原子比的负载Pd–Au合金纳米粒子在温和的反应条件下起着高活性的多相催化剂的作用。通过X射线衍射，X射线吸收光谱（XAS）和透射电子显微镜对负载的Pd-Au合金催化剂的结构表征表明，在载体上形成了均匀大小约为3 nm的无规Pd-Au合金纳米颗粒。此外，XAS和X射线光电子能谱阐明了从Pd到Au的电荷转移以及低Pd / Au比的无规Pd-Au合金中孤立的单个Pd原子的形成，

  DOI：

  10.1021/acscatal.6b02767

文献信息

• Stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone using cationic rhodium complex-catalyzed 1,4-hydrosilylation
  作者：Gen Onodera、Ryosuke Hachisuka、Tomomi Noguchi、Hiroki Miura、Toru Hashimoto、Ryo Takeuchi

  DOI：10.1016/j.tetlet.2013.10.085

  日期：2014.1

  The stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone is reported. Highly (Z)-selective conditions were the use of [Rh(cod)2]BF4/DPPE at room temperature with no solvent, whereas (E)-selective conditions were the use of [Rh(cod)2]BF4/P(1-Nap)3 (1-Nap = 1-naphthyl) under refluxing dichloromethane.

  据报道从相同的无环α，β-不饱和酮立体合成（E）-或（Z）-甲硅烷基烯醇醚。高度（Z）选择性条件是在室温下无溶剂下使用[Rh（cod）2 ] BF 4 / DPPE，而（E）选择性条件是使用[Rh（cod）2 ] BF 4 /在回流的二氯甲烷下，P（1-Nap）3（1-Nap ＝ 1-萘基）。
• Palladium-Catalyzed Preparation of Silyl Enolates from α,β-Unsaturated Ketones or Cyclopropyl Ketones with Hydrosilanes
  作者：Yuto Sumida、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/jo901513v

  日期：2009.10.16

  α,β-Unsaturated ketones and cyclopropyl ketones undergo palladium-catalyzed hydrosilylation with hydrosilanes to yield (Z)-silyl enolates.

  α，β-不饱和酮和环丙基酮与氢化硅烷进行钯催化的氢化硅烷化反应，生成（Z）-甲硅烷基烯醇化物。
• Graphene-enhanced platinum-catalysed hydrosilylation of amides and chalcones: a sustainable strategy allocated with in situ heterogenization and multitask application of H₂PtCl₆
  作者：Ning Li、Xiao-Yun Dong、Jing-Lei Zhang、Ke-Fang Yang、Zhan-Jiang Zheng、Wei-Qiang Zhang、Zi-Wei Gao、Li-Wen Xu

  DOI：10.1039/c7ra10541j

  日期：——

  simple hydrosilylation-type reduction could be further used in the 1,4-hydrosilylation of chalcones. The rationally designed and in situ formed Pt@G@Si nanocatalyst is demonstrated to be highly effective in the 1,4-hydrosilylation of α,β-unsaturated enones, allowing for the facile synthesis of a variety of otherwise inaccessible substituted silyl enolates. In addition, with the aid of platinum catalyst

  我们描述了在不同的有机转化中综合利用铂催化剂的新可持续战略，其中由简单的氢化硅烷化型还原制备的有机硅/石墨烯负载的铂催化剂可以进一步用于查耳酮的1,4-氢化硅烷化中。事实证明，合理设计和原位形成的Pt @ G @ Si纳米催化剂在α，β-不饱和烯酮的1,4-氢化硅烷化中非常有效，从而可以轻松合成各种本来无法获得的取代的甲硅烷基烯醇酸酯。另外，在这项工作中，还报道了借助铂催化剂残留物和TBAF，将一锅下游迈克尔取代的烯丙基甲硅烷基化物添加到丙烯酸烷基酯中。
• Rhodium-Catalyzed, Efficient Deutero- and Tritiosilylation of Carbonyl Compounds from Hydrosilanes and Deuterium or Tritium
  作者：Miguel Rubio、Jesús Campos、Ernesto Carmona

  DOI：10.1021/ol202117t

  日期：2011.10.7

  A cationic rhodium compound which is an active catalyst for both the hydrogen isotope exchange in hydrosilanes and the hydrosilylation of carbonyl compounds permits, in a one-flask, two-step procedure, efficient deutero- and tritiosilylations using SiEt3H under D-2 (0.5 bar) or T-2, at low catalyst loadings (0.1-0.5 mol%).
• Controlled Hydrosilylation of Carbonyls and Imines Catalyzed by a Cationic Aluminum Alkyl Complex
  作者：Jürgen Koller、Robert G. Bergman

  DOI：10.1021/om2008277

  日期：2012.4.9

  The synthesis, characterization, and unprecedented catalytic activity of cationic aluminum alkyl complexes toward hydrosilylation are described. X-ray crystallographic analysis of Tp*AlMe2 (1) and [Tp*AlMe][I-3] (3) revealed the preference of Al for a tetrahedral coordination environment and the versatility of the Tp* ligand in stabilizing Al in bi- and tridentate coordination modes. [Tp*AlMe][MeB(C6F5)(3)] (2) is highly active toward the hydrosilylation of a wide variety of carbonyls and imines, thus providing an inexpensive and versatile alternative to late transition metal catalysts.