acetic acid 1-(dimethylphenylsilyl)prop-2-enyl ester | 127541-72-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: acetic acid 1-(dimethylphenylsilyl)prop-2-enyl ester
• 英文别名: 1-(acetyloxy)-1-(dimethylphenylsilyl)-2-propene；1-[Dimethyl(phenyl)silyl]prop-2-enyl acetate
• CAS: 127541-72-4
• 化学式: C₁₃H₁₈O₂Si
• 分子量: 234.37
• InChiKey: DKHOQSPCFUJQBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  298.9±33.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  acetic acid 1-(dimethylphenylsilyl)prop-2-enyl ester 以 四氢呋喃 、 氯仿 为溶剂， 生成 (η3-1-acetoxy-allyl)(1,2-bis(diphenylphosphino)ethane)palladium(II) tetrafluoroborate
  参考文献：
  名称：

  Synthesis and structural features of α-acyloxy-(η3-allyl)palladium complexes

  摘要：

  alpha-Acetoxy (eta(3)-allyl)palladium complexes were prepared from acyloxy functionalized allylsilanes under mild conditions and in good isolated yields. The substituent and ligand effects of the acetoxy group on the palladium-allyl bonding were studied by X-ray diffraction. These studies show that the acetoxy group generates a strongly deformed bonding between the metal atom and the allyl moiety. This unsymmetrical bonding is modulated by the sigma-donor/pi-acceptor properties of the ligands. The C-13 NMR studies indicated that the shift values correlate with the carbon-palladium bond lengths and the inductive effects of the acetoxy group. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.05.013
• 作为产物：
  描述：

  1-(dimethylphenylsilyl)prop-2-en-1-ol 、 乙酸酐 在 吡啶 作用下， 以85%的产率得到acetic acid 1-(dimethylphenylsilyl)prop-2-enyl ester
  参考文献：
  名称：

  Enzymatic kinetic resolution of α-hydroxysilanes

  摘要：

  The enzymatic kinetic resolution of alpha-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various alpha-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active alpha-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.030

文献信息

• Palladium Pincer Complex Catalyzed Substitution of Vinyl Cyclopropanes, Vinyl Aziridines, and Allyl Acetates with Tetrahydroxydiboron. An Efficient Route to Functionalized Allylboronic Acids and Potassium Trifluoro(allyl)borates
  作者：Sara Sebelius、Vilhelm J. Olsson、Kálmán J. Szabó

  DOI：10.1021/ja052885q

  日期：2005.8.1

  Palladium-catalyzed boronation of vinyl cyclopropane, vinyl aziridine, and allyl acetate substrates could be accomplished using tetrahydroxydiboron reagent in the presence of SeCSe pincer complex catalyst 1a. These reactions result in allyl boronic acids, which were converted to synthetically useful trifluoro(allyl)borates or allyl boronates. The catalytic transformations proceed under mild and neutral

  钯催化的乙烯基环丙烷、乙烯基氮丙啶和乙酸烯丙酯底物的硼化可以在 SeCSe 钳形配合物催化剂 1a 存在下使用四羟基二硼试剂完成。这些反应产生烯丙基硼酸，其被转化为合成有用的三氟（烯丙基）硼酸酯或烯丙基硼酸酯。催化转化在温和和中性条件下进行，因此可以耐受许多官能团 Br、COOEt、ArSO2(NH)、OAc 和 SiRMe2。所提出的方法的选择性非常高，提供了包含反式双键的线性产品。