88075-18-7

基本信息
(4-羥苯炔基)三甲基硅烷
(4-羥苯乙炔基)三甲基硅烷
4-[(三甲基硅基)乙炔基]苯酚
4-((三甲基甲硅烷基)乙炔)苯酚
4-((三甲基甲硅烷基)乙炔基)苯酚
4-((Trimethylsilyl)ethynyl)phenol
4-[2-(TriMethylsilyl)ethynyl]-phenol
Phenol, 4-[2-(trimethylsilyl)ethynyl]-
物理化學(xué)性質(zhì)
制備方法

540-38-5

1066-54-2

88075-18-7
以4-碘苯酚和三甲基硅乙炔為原料合成(4-羥苯炔基)三甲基硅烷的一般步驟如下:將4-碘苯酚(2g,9.09mmol,1當(dāng)量)溶解于20mL無水甲苯中。向該溶液中依次加入PdCl2(PPh3)2(191.4mg,0.27mmol,0.03當(dāng)量)、碘化銅(I)(172.8mg,0.909mmol,0.1當(dāng)量)、N,N-二異丙基乙胺(1.58mL,9.09mmol,1當(dāng)量),隨后加入三甲基硅乙炔(1.28mL,9.09mmol,1當(dāng)量)。將反應(yīng)混合物在室溫下攪拌24小時(shí)。反應(yīng)完成后,蒸發(fā)除去溶劑,殘余物通過柱色譜法(洗脫劑:EtOAc/己烷=1:10)進(jìn)行純化,得到目標(biāo)產(chǎn)物(4-羥苯炔基)三甲基硅烷(1.73g,定量收率),為棕色油狀物。產(chǎn)物結(jié)構(gòu)經(jīng)1H-NMR(CDCl3, 500MHz)和13C-NMR(CDCl3, 75MHz)確認(rèn):1H-NMR δ 7.37(2H, d, J = 8.8Hz, Ar-H),6.76(2H, d, J = 8.8Hz, Ar-H),4.92(1H, brs, Ar-OH),0.24(9H, s, -Si(CH3)3);13C-NMR δ 155.76, 133.69, 115.49, 115.31, 105.02, 92.50, 0.05。
參考文獻(xiàn):
[1] Chemical Communications, 2009, # 39, p. 5832 - 5834
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 37, p. 9311 - 9316
[3] Angew. Chem., 2012, vol. 124, # 37, p. 9445 - 9450,6
[4] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1247 - 1249
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2015, vol. 70, # 9, p. 637 - 641