2-(trimethylsilyl)propanal | 18146-04-8

• 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: 2-(trimethylsilyl)propanal
• 英文别名: 2-trimethylsilylpropanal；2-trimethylsilanyl-propionaldehyde；2-Trimethylsilyl-propionaldehyd；2-Trimethylsilyl-1-propanal
• CAS: 18146-04-8
• 化学式: C₆H₁₄OSi
• 分子量: 130.262
• InChiKey: LSUMROSSVWBUMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  乙烯基三甲基硅烷 生成 2-(trimethylsilyl)propanal
  参考文献：
  名称：

  MAGOMEDOV, G. K. -I.;MOROZOVA, L. V., ZH. OBSHCH. XIMII, 1981, 51, N 10, 2266-2270

  摘要：

  DOI：

文献信息

• Iron Catalyzed Hydroformylation of Alkenes under Mild Conditions: Evidence of an Fe(II) Catalyzed Process
  作者：Swechchha Pandey、K. Vipin Raj、Dinesh R. Shinde、Kumar Vanka、Varchaswal Kashyap、Sreekumar Kurungot、C. P. Vinod、Samir H. Chikkali

  DOI：10.1021/jacs.8b01286

  日期：2018.3.28

  4-chloro styrene (S18), 4-vinylbenzonitrile (S19), 4-vinylbenzoic acid (S20), and allyl benzene (S21) to corresponding aldehydes in good to excellent yields. Both electron donating and electron withdrawing substituents could be tolerated and excellent conversions were obtained for S11-S20. Remarkably, the addition of 1 mol % acetic acid promotes the reaction to completion within 16-24 h. Detailed mechanistic

  地球上储量丰富的第一排过渡金属为稀有和贵金属提供了一种廉价且可持续的替代品。然而，在催化中使用第一行金属需要苛刻的反应条件，活性有限，并且不能耐受官能团。这里报道的是一种在温和条件下高效铁催化的烯烃加氢甲酰化反应。该协议在低于 100 °C 的 10-30 bar 合成气压力下运行，利用现成的配体，并适用于一系列烯烃。因此，铁前体 [HFe(CO)4]-[Ph3PNPPh3]+ (1) 在三苯基膦存在下催化 1-己烯 (S2)、1-辛烯 (S1)、1-癸烯 (S3) 的加氢甲酰化, 1-十二烯 (S4), 1-十八烯 (S5), 三甲氧基(乙烯基)硅烷 (S6), 三甲基(乙烯基)硅烷 (S7), 腰果酚 (S8), 2,3-二氢呋喃 (S9), 烯丙基丙二酸(S10), 苯乙烯 (S11), 4-甲基苯乙烯 (S12), 4-异丁烯-苯乙烯 (S13), 4-丁丁-苯乙烯 (S14), 4-甲氧基苯乙烯
• Magomedov, G. K.-I.; Morozova, L. V.; Sigachev, S. A., Journal of general chemistry of the USSR, 1986, vol. 56, p. 984 - 987
  作者：Magomedov, G. K.-I.、Morozova, L. V.、Sigachev, S. A.、Krivykh, V. V.、Taits, E. S.、Rybinskaya, M. I.

  DOI：——

  日期：——
• Magomedov, G. K.-I.; Morozova, L. V., Journal of general chemistry of the USSR, 1981, p. 1947 - 1950
  作者：Magomedov, G. K.-I.、Morozova, L. V.

  DOI：——

  日期：——
• Hydroformylation of alkenes having organosilicon substituents
  作者：Ryo Takeuchi、Nobuhiro Sato

  DOI：10.1016/0022-328x(90)87193-h

  日期：1990.8
• 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).