3-(三乙基甲硅烷基)丙醛 | 15184-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(三乙基甲硅烷基)丙醛
• 英文名称: 3-(Triethylsilyl)propanal
• 英文别名: 3-triethylsilanyl-propionaldehyde；3-Triaethylsilyl-propionaldehyd；3-Triethylsilylpropionaldehyd；3-Triethylsilylpropanal
• CAS: 15184-39-1
• 化学式: C₉H₂₀OSi
• 分子量: 172.343
• InChiKey: RPEYZWJSTOSYGE-UHFFFAOYSA-N

物化性质

• 沸点：
  77-78 °C(Press: 5 Torr)
• 密度：
  0.8693 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (allyloxy)triethylsilane 在 六甲基磷酰三胺 、 叔丁基锂 、 三氯乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 2.75h， 生成 3-(三乙基甲硅烷基)丙醛
  参考文献：
  名称：

  在硅上的不对称Retro- [1,4] Brook重排及其立体化学过程。

  摘要：

  DOI：

  10.1002/anie.200503734

文献信息

• Sadych-Sade; Petrow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3194,3196; engl. Ausg. S. 3159, 3160
  作者：Sadych-Sade、Petrow

  DOI：——

  日期：——
• The regioselective hydroformylation of vinylsilanes. a remarkable difference in the selectivity and reactivity of cobalt, rhodium, and iridium catalysts
  作者：Cathleen M. Crudden、Howard Alper

  DOI：10.1021/jo00090a029

  日期：1994.6

  The zwitterionic rhodium complex, Rh(COD)BPh(4), produces 2-(trimethylsilyl)propanal selectively in the hydroformylation of trimethylvinylsilane under quite mild conditions [100 degrees C, 200 psi (CO:H-2 = 1:2), 1.5-3 h]. Excess hydrogen is crucial for obtaining the branched aldehyde as the major product (B:L = 70:30). This is the first reported example of an alpha-selective hydroformylation of vinylsilanes. The potentially useful alpha-silyl aldehydes are difficult to prepare and isolate by other means, but using this procedure they can be obtained in one step from commercially available vinyltrimethylsilane, albeit in low isolated yields (20-30%). The addition of as little as 2 equiv of PPh(3) causes a complete shift in the selectivity yielding the linear isomer as the major product in the hydroformylation of vinyltriethylsilane (B:L = 7:93). The isolated yield increases from 30% to 91% after only 1.5 h. Iridium catalysts yielded the linear aldehydes (3-(trialkylsilyl)propanal) with excellent regioselectivities (90-100%) without the addition of any phosphine. A competing reaction is hydrogenation of the starting material. This can be suppressed by increasing the amount of CO in the gas mixture (CO:H-2 = 7:1). Of those complexes examined, hydrated IrCl3 (after preactivation at 160 degrees C) gave the best selectivity for the linear isomer (98-100%). The cationic complex, [Ir(COD)(2)](BF4-)-B-+, also gave the linear aldehyde predominantly (95-97%) in 75-80% yields. Although most of the cobalt complexes tested were unreactive, the cationic cobalt cluster [Co-3(eta(6)-C6H6)(3)(mu(3)-CO)(2)]BPh(4) was the most active catalyst for the hydroformylation of vinyltriethylsilane. At 100 degrees C, this complex completed six turnovers per minute, yielding the linear silyl aldehyde as the major product (B:L = 24:76).
• Containing Nitrogen and Phosphorus Porous Organic Polymer-Supported Rhodium Catalyst for Hydroformylation of Olefins
  作者：Yongcheng Lan、Dong Yun、Chungu Xia、Bo Qian、Jianhua Liu

  DOI：10.1007/s10562-024-04602-4

  日期：——
• Asymmetric Retro-[1,4] Brook Rearrangement and Its Stereochemical Course at Silicon
  作者：Atsuo Nakazaki、Takeshi Nakai、Katsuhiko Tomooka

  DOI：10.1002/anie.200503734

  日期：2006.3.27