88075-18-7 (4-羟苯炔基)三甲基硅烷

运输信息：冰袋运输。危险描述：危险性质：否。海关编码：2931900090

化学合成

化学合成

路线1：以4-碘苯酚和三甲基硅乙炔为原料合成(4-羟苯炔基)三甲基硅烷

• 原料：4-碘苯酚（2g，9.09mmol，1当量）、三甲基硅乙炔（1.28mL，9.09mmol，1当量）、PdCl₂(PPh₃)₂（191.4mg，0.27mmol，0.03当量）、碘化铜(I)（172.8mg，0.909mmol，0.1当量）、N,N-二异丙基乙胺（1.58mL，9.09mmol，1当量）、无水甲苯（20mL）
• 步骤：将4-碘苯酚溶解于无水甲苯中，依次加入PdCl₂(PPh₃)₂、碘化铜(I)、N,N-二异丙基乙胺，随后加入三甲基硅乙炔；室温搅拌24小时；蒸发溶剂，残余物经柱色谱（EtOAc/己烷=1:10）纯化
• 收率：定量（1.73g）
• 产物性状：棕色油状物
• 结构确认：¹H-NMR（CDCl₃,500MHz）δ7.37（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（CDCl₃,75MHz）δ155.76,133.69,115.49,115.31,105.02,92.50,0.05
• 参考文献：[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；[6] Organic Letters, 2014, vol.16, #3, p.948-951；[7] Chemistry - A European Journal, 2014, vol.20, #25, p.7655-7664；[8] ChemMedChem, 2013, vol.8, #3, p.521-526；[9] European Journal of Organic Chemistry, 2014, vol.2014, #7, p.1547-1556；[10] European Journal of Organic Chemistry, 2014, vol.2014, #7, p.1547-1556；[11] Tetrahedron, 2004, vol.60, #44, p.9977-9982；[12] Journal of Chemical Research, 2007, #12, p.728-732；[13] Angewandte Chemie - International Edition, 2016, vol.55, #40, p.12243-12247；[14] Angew. Chem., 2016, vol.128, #40, p.12431-12435,5；[15] Angewandte Chemie - International Edition, 2010, vol.49, #50, p.9644-9647；[16] Macromolecules, 2011, vol.44, #14, p.5693-5700；[17] Tetrahedron Letters, 2013, vol.54, #13, p.1761-1764；[18] Molecular Crystals and Liquid Crystals, 2014, vol.588, #1, p.17-27；[19] Chemistry - A European Journal, 2011, vol.17, #33, p.9164-9179；[20] Angewandte Chemie - International Edition, 2010, vol.49, #2, p.419-423；[21] Journal of the American Chemical Society, 2012, vol.134, #5, p.2766-2774；[22] RSC Advances, 2013, vol.3, #11, p.3697-3706；[23] Patent: WO2018/160967, 2018, A1. Location in patent: Page/Page column 85-86；[24] Dalton Transactions, 2007, #35, p.3885-3892；[25] Journal of Polymer Science, Part A: Polymer Chemistry, 2018, vol.56, #16, p.1884-1893；[26] Patent: JP2018/145124, 2018, A. Location in patent: Paragraph 0068; 0069；[27] Tetrahedron Letters, 2002, vol.43, #39, p.7091-7094；[28] Patent: EP1215195, 2002, A1. Location in patent: Scheme 6；[29] Canadian Journal of Chemistry, 2008, vol.86, #5, p.410-415；[30] ACS Chemical Neuroscience, 2015, vol.6, #8, p.1317-1330；[31] European Journal of Organic Chemistry, 2015, vol.2015, #30, p.6710-6726；[32] Chemical Communications, 2016, vol.52, #90, p.13237-13240