(E)-2-(1-triethylsilanyl-hept-1-enyl)-benzaldehyde

• 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: (E)-2-(1-triethylsilanyl-hept-1-enyl)-benzaldehyde
• 英文别名: (E)-2-[1-(triethylsilyl)hept-1-enyl]benzaldehyde；2-[(E)-1-triethylsilylhept-1-enyl]benzaldehyde
• 化学式: C₂₀H₃₂OSi
• 分子量: 316.559
• InChiKey: CRDCSLBUERPADA-CAPFRKAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘苯甲醛 在 platinum(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (E)-2-(1-triethylsilanyl-hept-1-enyl)-benzaldehyde
  参考文献：
  名称：

  Platinum Oxide Catalyzed Hydrosilylation of Unsymmetrical Internal Aryl Alkynes under Ortho-Substituent Regiocontrol

  摘要：

  [GRAPHICS]PtO2- and H2PtCl6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed and compared. The regioselectivity of the H-Si bond addition was found to be controlled by the ortho substituent rather than the nature of the platinum catalyst. Arylallcynes with an ortho substituent, regardless of its electronic nature, directed the silyl substituent mainly to the a-position. PtO2 proved to be a versatile and powerful catalyst compared to H2PtCl6 since it prevents the alkyne reduction.

  DOI：

  10.1021/ol052245s

文献信息

• Regiochemical Aspects of the Platinum Oxide Catalyzed Hydrosilylation of Alkynes
  作者：Mouâd Alami、Abdallah Hamze、Olivier Provot、Jean-Daniel Brion

  DOI：10.1055/s-2007-983742

  日期：2007.7

  The platinum-catalyzed hydrosilylation of unsymmetrical substituted arylalkynes with various hydrosilanes was investigated and the reaction selectivity of various para-substituted substrates was compared with that of their corresponding ortho-substituted derivatives. We showed that heterogeneous platinum oxide is a very efficient catalyst for such hydrosilylations and that H-Si bond addition proceeds in a stereoselective cis-fashion. The regioselectivity was found to be under the control of the ortho-substituent rather than due to the nature of the platinum catalyst. Aryl­alkynes with an ortho-substituent provided predominantly to exclusively α-selectivity, regardless of the electronic nature of the substituent. The precise contributions of steric, electronic, and coordinative factors controlling the regioselectivity of the H-Si bond addition are discussed.

  对不对称取代的芳基炔与各种氢硅烷的铂催化氢硅化反应进行了研究，并比较了不同对位取代底物的反应选择性与其相应的邻位取代衍生物的反应选择性。我们展示了异相铂氧化物是一种高效的催化剂用于此类氢硅化反应，且H-Si键的加成以立体选择性的顺式方式进行。区域选择性被发现是由邻位取代基控制，而不是由铂催化剂的性质决定。带有邻位取代基的芳基炔提供了主要到完全的α-选择性，无论取代基的电子性质如何。我们还讨论了影响H-Si键加成的区域选择性的立体、电子和配位因素的精确贡献。
• Platinum Oxide Catalyzed Hydrosilylation of Unsymmetrical Internal Aryl Alkynes under Ortho-Substituent Regiocontrol
  作者：Abdallah Hamze、Olivier Provot、Mouâd Alami、Jean-Daniel Brion

  DOI：10.1021/ol052245s

  日期：2005.12.1

  [GRAPHICS]PtO2- and H2PtCl6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed and compared. The regioselectivity of the H-Si bond addition was found to be controlled by the ortho substituent rather than the nature of the platinum catalyst. Arylallcynes with an ortho substituent, regardless of its electronic nature, directed the silyl substituent mainly to the a-position. PtO2 proved to be a versatile and powerful catalyst compared to H2PtCl6 since it prevents the alkyne reduction.